Inorganic Pharmaceutical & Medicinal Chemistry Organic Pharmaceutical & Medicinal Chemistry
Inorganic Pharmaceutical & Medicinal Chemistry Organic Pharmaceutical & Medicinal Chemistry
Inorganic Pharmaceutical & Medicinal Chemistry Organic Pharmaceutical & Medicinal Chemistry
INORGANIC PHARMACEUTICAL
& MEDICINAL CHEMISTRY
ORGANIC PHARMACEUTICAL
& MEDICINAL CHEMISTRY
GENERAL CHEMISTRY
ORGANIC CHEMISTRY
INORGANIC CHEMISTRY
INORGANIC COMPOUNDS
GENERAL CHEMISTRY Matter
Composition/Constituents:
(3) changes that matter undergoes
(4) energy involved in such Elements Compounds
changes
Pure
Impure/ Mixture
composed predominantly of
atoms, molecules, ions - Time - Second Proportion Suspension
interconvertible w/ energy
▪ Mass refers to the amount of - Temperature - Kelvin Colloids
matter present in the material ▪
Weight = Mass x pull of gravity Classification of Matter:
Units of Measurement Homogenous
*Law of Heterogenous
Fundamental Quantity SI U Definite
Proportion
- Length - Meter
*Law of Solution
- Mass - Kilogra Multiple
Properties of Matter 1 kind of material or atom
(1) Intensive/ Intrinsic mass independent has definite chemical composition
are characteristics of any sample of the cannot be decomposed by simple physical/
substance regardless of the shape or size of the chemical means into two or more different substances
sample ▪ Compound substance composed of two or more elements unites
Examples: *Density *Melting point chemically in definite proportion
*pH *Freezing point cannot be changed into sipler substance under
*Color *Sublimation temperature normal laboratory conditions
*Concentration *Optical activity
▪ Element simplest form of matter
*Law of Definite Proportions always the same regardless
*Boiling point
same w/ Law Constant Composition Elements
(2) Extensive/ Extrinsic mass dependent
combined in different ratios of whole numbers to
Examples: *Volume
form different
*Weight
compounds
*Pressure
*Law of Multiple Proportions
*Heat content
Elements combined in fixed ratios of whole
*Temperature
numbers to form compounds states that the
elemental composition of a pure compound is
Changes that Matter undergoes:
has solid like properties
(1)Physical Change change in phase
resemble those of a crystal in the formation of loosely
(2)Chemical Change in both intrinsic & extrinsic
ordered molecular arrays similar to a regular crystalline
properties Evidences of Chemical Change:
lattice & anisotropic refraction of light
*Evolution of Gas
-Crystal lattice ordered arrangement of atoms
*Formation of a precipitate
-flow properties
*Emission of light
-LCD liquid crystal display
*Generation of Electricity
*Two main types of Liquid Crystals:
*Production of Mechanical Energy
*Absorption/liberation of Heat -Smectic (soap- or grease-like)
-Nematic (thread-like)
Physical State/ Phase *Six Distict Crystal System:
a. solid (lowest) 1. Cubic (sodium chloride)
b. liquid 2. Tetragonal (urea)
c. gas (highest) 3. Hexagonal (iodofrom)
d. Plasma aka “Mesophase”, “Liquid Crystals” 4. Rhombic (iodine)
5. Monoclinic (sucrose)
6. Triclinic (boric Acid) 3. Freezing from liquid to solid, caused by cooling a liquid. 4.
▪ Mixture composed of two or more elements/ substances which Boiling from liquid to gaseous (vapor) at a temperature called
are not chemically combined boiling point.
5. Evaporation from liquid to gaseous (vapor) due to the escape
Classification of Mixture of molecule from the surface.
▪ Heterogenous two or more distinct phases Vapor refers to the gaseous phase of a substance, which
▪ Homogenous only one phase or single phase is normally liquid or solid at room temperature.
-Solution uniform mixture 6. Liquefaction from gas to liquid at a substance which is gas at
composed of solute & solvent room temperature & pressure. It is caused by
wherein atoms, molecules or ions of the substance cooling & increasing pressure.
become dispersed 7. Condensation from gaseous to liquid, of a substance which is
-Suspension homogenous dispersion insoluble in a liquid a liquid at room temperature & pressure. It is
aka Coarse Mixture naturally caused by cooling.
finely divided solid materials distributed in a 8. Sublimation from solid to gaseous on heating, & from
liquid gaseous directly to solid on cooling.
-Colloids contain particles bigger than those in solutions but 9. Deposition direct transition from vapor state to the solid state
smaller that those in suspension
particle of solute are not broken down to the size of Process of Separating Components of Mixture:
the molecules but are small dispersed throughout 1. Decantation Difference in Specific Gravity
the medium. 2. Distillation Evaporation & then condensation
exhibit the light scattering effect 3. Magnetic separation for metals
Properties of Colloids 4. Sorting mechanical separation; darbling
1. Tyndall Effect light scattering effect 5. Filtration solid to liquid
2. Brownian Movement zigzag movement of 6. Centrifugation speeding up of settling process of a precipitate
colloidal particles 7. Functional Crystallization lowering of temperature so that the
3. Electrically charge more insoluble component crystallizes
*Electrophoresis Gel-electrophoresis out first.
SDS-PAGE 9. Chromatography difference in solvent affinity
(used to separate
protein & nucleic acids) Process involved in Chemical Change:
-Cathode (−) reduction takes place 1. Combustion chemical union of oxygen w/ another substance
-Anode (+) oxidation takes place 2. Reduction oxygen is removed from compound or H is added
4. Adsorption 3. Neutralization acid reacts with a base to form salt & water 4.
Other Laws of Chemical Changes: Hydrolysis reaction of water on a salt forming an acid and base
*Rate of Hydrolysis depends on: pH of the solution
*Law of In a chemical reaction, the total mass
Temperature
Conservation of of reactant is equal to the total mass of
5. Saponification a reaction between an alkali & fats/ oils
Mass products or mass is neither created nor
forming soap & glycerol
destroyed in any transformation of
6. Fermentation action of bacterial/ microorganism on organic
matter. by Antoine Van Lavoisier
substances resulting to the production of
alcohol.
12
32 2−
S 16 18 16
16 Meyer & Mendeleev (Lothar Meyer & Dmitri
Mendeleev) First Periodic Law
*Isotopes same elements, same 3 of protons, “The Physical & Chemical Properties
different # of neutrons are periodic functions of their atomic weight”
same atomic #; different mass number Moseley (Henry Moseley)
Classes: (1) Stable elements are arranged based on atomic numbers
(2) Unstable or Radioactive Isotopes − increasing atomic number
*Isobars different elements, same mass #
*Isotones different elements, same # of neutrons
*Negatron → neutron converts to proton
*Positron → protron changes to neutron
▪ Allotropism
Allotrope atoms of different elements can link together in different
ways to form substances with different properties.
Principles:
Pauli’s Exclusion Principle
No two electrons can have the same set of quantum number
Each atomic orbital can only accommodate 2 electrons (Ex: 1s2)
Aufbau/ Building Up Principle
energy: Lower Higher (lower energy levels are filled up
first) the higher the n value, the higher the energy level
* 4s: (n+Ɩ) = 4+0 = 4 (energy level)
Hund’s Rule of Maximum Multiplicity
orbital are filled up singly before pairing up.
Heisenberg Uncertainty (4f) −1st 14 elements
It is impossible to determine simultaneously the momentum = Lanthanoids/ Lanthanide series/ Rare Earth Metals
& position of an electron.
= 57-70th element
Periodic Table:
(5f) −2 14 elements
nd
Antoine-Laurent Lavoisier
= Actinoids/ Actinide Series/ Heavy Rare Earth Metals
Father of Modern Chemistry
first true periodic table = 89-102th element
*Base on classes: −Gases− −Metals− −Minerals−
Oxygen Fe Chalk Group/ Family: Column; Top to Bottom (18
Nitrogen Co Silica groups/families) Period: Row; Left to Right (7 periods)
Chlorine Cu
Dobereiner (Johann Dobereiner)
proposed the Law of ”TRIADS” based on physical &
chemical properties of elements. Summary: Periodic Properties
Li, Na, K, TB LR
Ca, Ba, Sr,
S, Sc, Tc
1. Atomic Size/
Newlands (John Newlands)
“octaves” (set of eight)
LR = IP
Atomic Radius
*Noble Gases very high IP
3. Electron affinity is the amount of energy release when a neutral
2. Ionization Energy Potential atom accepts an electron in its outermost shell
to convert
3. Electron Affinity it to negatively charge ion.
is the energy change that occurs when an electron is
4. Electronegativity added to a gaseous atom because it measures the
attraction of the atom for the added atom
5. Metallic Property TB = EA
LR = EA
Non-metallic Property 4. Electronegativity the tendency of an atom to attract
electrons to itself when its chemically
TB = Metallic Property & combined w/ another
Atomic size LR = Metallic atom.
TB = EN
Property & Atomic size
LR = EN
*Halogens very high EN (F> O> N ≉Cl)
5. Metallic Property: TB = metallic property
LR = metallic property
Periodic Properties:
Nonmetallic Property: TB = nonmetallic property
1. Atomic Size: w/ in Group (TB) = atomic size/ atomic
LR = nonmetallic property
radius w/ in the Period (LR) = atomic size/
*Metalloids directly below the ladder
atomic radius
are elment possessing both metallic & nonmetallic
2. Ionization Energy Potential is amount of energy required to
in character
remove en electron from a
-Boron
neutral
-Silicon
atom to convert it to positively charge
-Germanium
ion.
TB = IP
−Group IA VIIIA −Group IB VIIIB
Family A Family B -Arsenic -Antimony -Tellurium
−Representative Elements −s & p −Transition Elements −d & f blocks -Polonium
blocks
=����/���� ��
�� ��
6. Molality (m) more accurate ��
Supersaturated Solution ��
more solvent that solute �� =������ ��
��
=�������������
��������� ����
������������ ��
����
��������������
��
Colligative Properties ?FP = kfm
1. Vapor Pressure Lowering the addition of a non-volatile solute Freezing point of water is 0°C
lowers the VP of the liquid Kf= 1.86°C/m
A liquid in a closed container will established an 4. Osmotic Pressure
equilibrium with its vapor. Pressure needed to prevent osmosis
When equilibrium is reached, the vapor exerts a Osmosis net movement of solvent molecules through a
pressure (vapor pressure) semipermeable membrane from a more dilute solution to
Volatile exhibits vapor pressure a more concentrated solution
most use Lower Temperature Zone lower to higher concentration of solute
Nonvolatile no measurable vapor pressure Reverse Osmosis move under high pressure from
Raoult’s Law is applied in the determination of vapor more concentrated to less
pressure P= (1x Xsolute) P° concentrated
lowering of a vapor pressure of a solvent is equal to process of water purification
the product of the mole fraction of the solute & vapor Gas Laws (PV=nRT)
pressure of the solvent. 1. Boyle’s Law Volume is inversely proportional to
follow ideal solution pressure nonlinear relation for volume
?P=P° of pure solvent x mole fraction of the solute & pressure ��1��1 = ��2��2
2. Boiling Point Elevation Constant: n, R, T
Boiling Point equilibrium between the liquid & the gas, point Variable: P, V
at which the VP equals atmospheric P. Relationship: Inverse
3. Freezing Point Depression
Presence of salt/ solute will cause lowering of freezing
point Ice cream making
2. Charle’s Law Volume is directly proportional to 8. Grahams Law The rate of the effusion of two gases (&
temperature (Kelvin), 273K−standard diffusion) are inversely proportional to the
square roots of their densities providing
��1=��2 the temperature & pressure are the same
��1 for two gases.
��2 ��2 ����1
Constant: P, n, R
��1
Variable: V, T
Relationship: Direct ����2
*Diffusion gradual mixing of
3. Avogadro’s Law Volume is directly proportional to molecules of one gas w/ the
molecules of
moles ��1=��2 another gas by virtue of their kinetic
��1 properties
��2 *Effusion passage of a gas under
pressure through a small opening
Constant: P, R, T
Variable: V, n
Relationship: Direct
*Avogadro’s Number: 6.02 x 1023
Acids & Bases
4. Combined/ combination of Boyle’s, Charle’s, Electrolytes Allow conductase of electricity
Ideal Gas Law WEAK electrolytes: Incomplete/PartiaI dissolution
Avogadro’s ��1��1=��2��2 Poor electric conductor
��1��1 STRONG electrolytes: Strong acids & bases
Complete dissolution
��2��2 Best electric conductor
*Ideal Gas exist at STP Non-Electrolytes will not dissociate, will not conduct electricity
T= O°C / 273 K do not ionized in water
P= 1 atm
= 760 mmHg Acid-Base Theory
N= 1 mol ACID BASE
V= 22.4 L
Arrhenius yield H+ yield OH Bronsted-Lowry proton donor
*Ideal Gas Constant: R
proton acceptor Lewis e- acceptor e- donor
R= 0.08205 Latm/ mol k
R= 8.314 J/mol k
R= 1.987 cal/mol/k Arrhenius Theory water ion theory of Acidity
Bronsted-Lowry H+(hydronium ion)
5. Dalton’s Law State that the Pressure exerted by a conjugate acid-base pairs
of Partial Pressure mixture of gasses (non-reacting gases) is protonic concept
the sum of the partial pressures that elaborated as HA <-> H++ A
each gas in the mixture exert individually natural direction of a bronsted-lowry acid-base
gaseous mixtures reaction: SA+SB WA+WB
������������ = ���� + ���� * H30+ strongest acid in aqueous solution
+ ���� … ���� Lewis Theory coordinate covalent bond
*Heavy metals + chelating agents (2or more donor atoms)
EDTA -^ donor atoms
6. Gay-Lussac’s Pressure is directly proportional to
law or *Chelates (cage-like structures)
temperature, if V is constant
Amonton’s *Coordinate Covalent Bond − interaction wherein both lectrons in
Law the bond arise from a single orbital
on one of the atoms forming the
bond.
7.
Clausius-Clapeyron ��������2 1. SA + SB neutral salt
��1=∆���� (��2 − ��1) HCl + NaOH NaCl +H2O
2. SA + WB acidic salt
2.303 ����2��1 HCl + NH4OH NH4Cl + H2O
Where: P= Pressure 3. WA + SB basic salt
T= Temperature CH3COOH + NaOH NaCH3COO + H2O
ΔHv = heat of vaporization 4. WA+WB neutral, acidic, basic salt
R= gas constant + 8.314 J/molK CH3COOH + NH4OH NH4CH4COO + H20
* Latent heat heat required for kA = kB neutal
phase transition to kA>kB acidic salt
happen. kA<kB basic salt
-Hf heat of fusion (S⇌L)
-Hv heat of vaporization (L⇌G)
-Hs heat of sublimation (S⇌G)
*In a complex, the metal acts as a Lewis Acid (e- acceptor).
General Properties:
ACIDS sour taste
Alkali Metal NaOH
Litmus: Blue to Red
aqueous solutions conduct electricity (hydroxides) KOH
reacts with metal to produce Hydrogen gas LiOH
reacts with carbonate & bicarbonate
to produce Carbon dioxide gas Alkaline Earth Be(OH2)
turns colorless w/ Phenolphthalein (metal
turns pink w/ methyl orange indicator hydroxides)
Most common acids:
Strong Acids Weak Acids
B. Buffer Capacity
→ ability/ degree (magnitude) of a buffer solution to resist
changes in pH upon addition of acid/alkali
→depends on the amount of the acid & the base from which
the buffer can neutralize before pH begins to change to an
appreciable degree
Van slyke
∙ was responsible for a quantitative expression
∙ amount in g/l of strong acid or a strong base required to be
added to a solution to change its pH by 1 unit.
∙ higher buffer capacity, lower change in pH.
Pearson’s HSAB principle:
“Hard acids are electron acceptor w/ high positive charges & relatively
small sizes while soft acids have low positive charges & relatively large
sizes. “
Thermodynamics deals w/ energy transformation System ΔH = Hf − Hi
any part of the universe which is isolated from the rest by a B. Non-state Function path-dependent
boundary on a wall First Law of Thermodynamics
Surrounding everything outside the system “Law of Conservation of Energy”
Energy is not created nor destroyed, it can only be
Three Types of Thermodynamic System transformed. −The Energy of the universe is constant.
1. Open allow exchange of both matter & energy − ΔV = 9xw
-you can add/withdraw
2. Closed allows exchange of energy but not of matter 3. Second Law of Thermodynamics
Isolated does not allow the exchange of both matter & energy. “Spontaneous Law”
*Adiabatic doest not allow energy or heat flow A process that occurs by itself must be increased in the entropy in
*Diathermal allows energy & heat flow order to be SPONTANEOUS!
−accompanied by an increase of entropy
ΔG = (−) spontaneous
Thermodynamic Functions: ΔG = (+) non-spontaneous
1. Internal Energy (U or E) total energy content of a system, ΔG = (0) equilibrium
composed of thermal energy & chemical ΔG = ΔH −TΔS
energy (−) (+) (−) spontaneous
is the heat content of a system evaluated at (+) (−) (+) non-spontaneous
contant volume (+) (+) spontaneous
*Heat content = constant volume (isochoric) X X non-spontaneous
refers to the heat required to Above 0 degree − melt spontaneously
increase the internal energy & to
Below 0 degree − not melt spontaneously
perform work of expansion
2. Enthalpy (H) Energy of a reaction Exacly 0 − equilibrium
heat content evaluated at constant pressure − solid & liquid –Physical State @ Freezing point
*Heat content = constant pressure ( Isobaric) Triple Point the condition of temperature & pressure where a
3. Entropy (S) measure of degree of randomness or disorderliness of substance can exist solid, liquid & gas @ the same
a system. time
*If the Entropy is Zero, Freezing Point 0°C matter @ solid
the reaction is Spontaneous & Irreversible. Boiling Point matter @ liquid
4. Gibb’s Free Energy (G) expendable amount of
energy combines enthalpy & Third Law of Thermodynamics
entropy “The entropy of a pure crystalline solid at a zero Kelvin is zero.“
determines spontaneity of a reaction SOK = O
when a reaction is at equilibrium
= Gibbs Free Energy is Zero
*G=H−TS (ΔG=ΔH−TΔS)
5. Heat (q) an energy transfer due to temperature CHEMICAL REACTIONS:
1. Endothermic Process reaction wherein heat is absorbed by the
difference q = (+) endothermic
system, indicated by (+) change in enthalpy.
q = (−) exothermic
2. Exothermic Process a reaction wherein heat is released by the
6. Heat Capacity (c) the amount of heat required to raise the
system, indicated by a (−) change in enthalpy.
temperature of an object or substance by one
tend to be spontaneous reaction
degree.
6. Work (w) a form of energy transfer between a system & its
surroundings in the form of compression or expansion of
Chemical Kinetics (reaction rates):
the gas.
1. Collision Theory result of molecular collision
movement of an object against some force
rate & frequency of effective collisions
w = work
is effective if:
w= P2xtΔY
Requirements:
ΔV = 0 w= 0 a. Reactants must posses energy equal to or higher
*work done BY the system occurs during the process of than minimum energy requirement (energy barrier,
expansion (expansion) activation of energy [Ea])
ΔV = Vf − Vi b. Proper orientation reaction profile
sign is (−) A=B P
*work done ON the system occurs during Ea = rate
compression (compression) Ea = rate
sign is (+) #peaks = equal to the number of steps of reaction
*Converted Reaction/ Single Phase Reaction
single step reaction
A. State Function path independent; not concern w/ the process only determining Endo or Exo
in the initial & final state. from graph
Ex: ΔH, ΔV, ΔG, ΔS ΔH = H prod − H reactants
= (−) A B # collision
= Endothermic OO1
2. Transition State Theory reactant (first form) to transition state & O
dissociation to products
OO 2
*reactants transition state products
*Rate dependents on energy required for the formation of Chemical Equilibrium
transition state (TS)
energy TS =slow rate Kinetics rate of forward reaction is equal to rate of backward reaction
energy TS = fast rate
*Intermediate space occupied between two transition state (TS) Homogenous Equilibrium reactants & product are present in same phase.
Factors Affecting Reaction rate: Heterogenous Equilibrium the reactants & products are in different
1. Nature of Reactants reactivity, physical state 2. Temperature phase
temperature ∝Eave mobility frequency collision
rate
3. Surface Area Ionic Equilibria involves Ionia
SA particle size 1. Weak Acid & Weak Base
rate will be equal if they are have 1 aqueous solution
4. Concentration -weak acid: Ka =acid ionization constant
conc. rate -weak base: Ka = base ionization constant
Except for zero order reaction 2. Insoluble Salts happened if there saturated solution Ksp = solubility
product constant
Laws of Mass Action
reactant = collision
OO 3. Complexes: Kf = formation
O O3 constant
−when a stress is applied to an equilibrium
− stress factors: Δs in concentration: P, V, temp
Rate Law Expression = A=B P −will not cause any shift
rate = K [A] X[B]Y −addition of catalysy
Where: K = specific rate constant Ex: Δ(g) = 2B9g) ⇌ P(a)
= temp-dependent P (V) − shift to directions lesser # of gaseous
[A][B] = molar concentration molecules
X & Y = order of reaction
temp = favors an endothermic reaction
magnitude of the effects of the changing
temp = facvors an exothermic reaction
concentration of reaction rate
temp =
}3
x=1
y=2 temp =
5. Catalyst a substance that speed up the rate of reaction by
providing a new reaction pathway for molecules
influences the speed of a reaction without itself Common-ion Effects suppresses the ionization of weak
being altered chemically. electrolytes (the dissociation of a
*Effects: a. Directly lower EA weak
b. Can make reaction proceed in a multistep process wherein
Le Chatelier’s Principles
each step has lower Ea compared to the usual OH = H3O solution a strong electrolytes that in common
reaction Add of NaCl Na+Cl = No shift w/ the weak electrolyte)
Add of HCl H++ Cl− = Add of NaOH Na = electrolytes is decreasing by adding to the
ORGANIC CHEMISTRY
Organic Chemistry branched of chemistry that deals with carbon – containing compounds with: C, H, O, P, S, X (halides – F, Cl, B, I)
Hydrocarbon Derivatives are hydrocarbons that bear other carbon & hydrogen atoms & other
elements such as Oxygen, Nitrogen, Sulfur, or Halogen, Phosphorus, etc
Carboxylic Acid derivatives Tertiary Amines: R3N Organophosphate
-acid acyl 2. Heterocyclic Sulfur-containing
Oxygen-containing
-anhydrides 3. Nitrogen-compounds 1. Thiols (-SH)
1. Aldehydes (RCHO)
4. Carboxylic Acid -ester (RCOOR) Halogen -sulfur analogue of
Ketones (RCOR)
(Carboxyl, -COOH) -amides containing alacohols
2. Ethers (ROR)
Nitrogen-containing 1. Alkyl Halides 2. Aryl -aka “Sulfhydryls” 2.
-formed during
1. Amines (amino group, Halides Thioethers (R-S-R)
dehydration of alcohol
-NH) Primay Amines: RNH 2 Phosphorus-containing 1.
-CnH2n+20
*Organic acid (RCOOH) 5. Secondary Amines: R2NH Phosphate groups 2.
3. Alcohols (Phenol)
Isomerism refers to the existence of two or more compounds having ⇒ (1-butene) H2C=CH−CH2−CH3
the same molecular formula, but different structure ⇒ (2-butene) H2C−CH=CH2−CH3
Isomer compounds having the same Molecular formula, but C3H7Br
different structure. ⇒ (1-bromopropane) CH3− CH2−CH2−Br
Stereochemistry the branch of organic chemistry that is ⇒ (2-bromopropane) CH3− CH−CH3
solely dedicated to the study of isomers |
Br
Reasons: *Prefixes that designate positions in the benzene:
1. Order of Bonding (a) Ortho indicate substances on the benzene
“Structurally Isomer” ring in positions next to each other
a. Chain – branching
− exhibited by alkanes Ortho-bromochlorobenzene
− differ in the arrangement of C atoms
Ex: C4H10⇒ (butane) CH3−CH2−CH2−CH3 (b) Meta substituents on the benzene ring
⇒ (isobutane) CH3−CH−CH3 separated by one carbon atom.
|
CH3 Meta-bromochlorobenzene
C5H12 ⇒ (pentane) CH3−CH2−CH2−CH2−CH3
⇒ (isopentane) CH3−CH−CH2−CH3 (c) Para subtituents separated by two carbon
| atoms
CH3 Para-bromochlorobenzene
⇒(neopentane) CH3
| c. Functional Isomer − Functional Group
CH3−C−CH3 − differ in their functional groups
| Ex: CH2−CH2−OH ethanol (alcohol)
CH3 CH3−O−CH3 methyl ether (ether)
b. position − position of multiple bond or differ in the
position of substituent or functional group.
− differ in position of the substituent or
unsaturated bonds (C=C, C≡C) 2. Spatial Orientation arrangement of atom in
space “Stereoisomer”
Ex: C4H8 –alkene w/ 1 double bond
a. Geometric Isomers double bond (alken3),
cyclic *Cis-Trans 1. Chiral Center/ Chiral carbon/ Asymmetric chiral
-Cis (means on the same side) carbon aka Stereocenter
Ex: Cis −2−butene is acarbon to which four different atoms
or group of atoms are attached
2. No symmetry element
Enantiomers mirror images but not superimposable
-Trans (means across or on opposite sides) also called as Optical Isomer since they rotate light in
Ex: Trans−2−butene the opposite direction
Diastereomers non-mirror images, not
superimposable Mesocompounds mirror images,
superimposable
b. Conformational Isomers same compounds
(a) open chain/ acyclic can be obtain in Epimer special type of diastereomers
rotation along a single identical in all except in one chiral center
bond differ only in configuration at one asymmetry carbon
(b) cyclic-ring flipping atom ▪ D-glucose/ D-mannose Epimers at 2
Ex: ▪ D-glucose/ D-galactose Epimers at 4
Ethane Anomer differ only in configuration at Carbon #1
(carbonyl C or anomeric C)
Saw horse Projection:
Perspective Formula:
-dash (back) α-anomer β-anomer
-wedge (front)
Ex: Tartaric Acid
Newman Projection: HOOC−CH−CH−COOH
-eclipse conformation ||
OH OH
= # stereoisomers =2n (n=chiral center)
= 22
-staggered conformation: =4
-more stable
Fischer Projection Formula
Dihedral angle
I II III IV
Cyclobutane
-planar not a stable conformation
are all eclipsing
*Ideal Antiseptic
has a low surface tension
should also be non-irritating to tissue &
non-allergenic retain activity in the presence of
body fluids
rapid & sustained lethal action against microorganisms
Ethers
-aka Organic Oxides
R−O−R
Ar−O−Ar
Ar−O−R
-glycosidic bond formed in glycoside
Nomenclature fro Ethers
1. IUPAC Rules
-use alkoxy as a prefix
Aliphatic Amine Aromatic Amine
-position is indicated by number
-“OXY”
-CH3OCH3 CH3−NH2 -aniline
2. Derived Name
-alkyl groups + Ethers
-CH3OCH3
Classification of Ethers:
Basicity: Aliphatic Amine > Aromatic Amine
1. Open-chain
Classification based on the number of group attached
a. Symmetrical contains similar R groups
to N (1°, 2°, 3° & Quaternary Ammonium Compounds)
Ex: Methyl ether (Methoxy methane): CH2−O−CH3
Ethyl Ether (Ethoxy ethane): CH3−CH2−O−CH2−CH3
❖Important Amines:
b. Mixed contains different R groups
Ex:Ethymethyl ether (Methoxy ethane): 1. Aniline used to commercially in the preparation of many
CH3−CH2−O−CH3 dyes & drugs
2. Cyclic Ethers 2. Choline found in egg yolks, meats,& fish, essential for
a. Epoxides/ Oxiranes/ Oxacyclopropane growth 3. Adrenaline/ Epinephrine/ Norepinephrine a
cyclic ethers in which the ether oxygen is a part of a neurotransmitter Causes low
3-membered ring system 4. Amphetamine a psychomimetic drugs
Ex: Ethylene Oxide gas sterilant pH urine or
alkylation of essential 5. Methamphetamine
metabolism of bacteria alkaline
6. Pseudoephedrine
b. More than 3 members included in the ring system 7. Phenylpropanolamine
furanose ring: urine
8. Barbituric Acid parent compound of barbiturates
(sedatives) an addictive drug
pyranose ring: has both an amino & an acid group
9. Saccharin artificial sweetener, (disadvantage: bitter after
❖Important Ethers: taste) 10. Other amino-containing compounds: β-blockers
β-agonists
1. Ethyl Ether once widely used as general anesthetic because
it is safe even in long surgical procedures
ADR: Irritation of mucous membranes, nausea &
vomiting
dangerous because it is explosive * NH2 recentl discovered compound w/ a
solvent for waxes & fats composition of 87.5%N & 12.5% H
2. Ethylene oxide gas sterilant Aldehydes (RCHO)
used to fumigate textiles & grains undergone w/ Cannizaro Reaction
raw material in the synthesis of other organic are oxidized to carboxylic acids,
compound & reduced to primary alcohols
3. Monobenzone depigmenting agent in cases of excessive IUPAC: Parent chain contains the –CHO,
melanin formation same pattern as alkane,
− reduce melanin formation change –e to –al
− can be seen in whitening preparation terminal functional group
4. Eugenol from Clove Oil Example:
when mixed with ZNO forms a cement used by Methanal (formaldehyde)
dentist as temporary fillings
5. Naproxen NSAID
6. Gembrozil Ethanal (acetaldehyde)
Reactions of Aldehyde:
1. Reaction w/ 2,4-DNPH
Amines organic compounds that are derived from −forms highly colored 2,4 –DNP Hydrazones
ammonia by replacing 1, 2, or 3 H’s w/ alkyl or aryl (Ar)
which range from yellow to deep red
Primary Amines: RNH2 2. Oxidation:
Secondary Amines: R2NH (a) Benedicts Test traditional test forn glucose in the urine
Tertiary Amines: R3N *Basis: reduction of cupric ions to
Quaternary Amines not basic, no lone pair of electrons cuprous
*amino group: −NH oxide
*R-group: e- donor brick red ppt (for Aliphatic only;
causes: sterric effect (“crowding”) also for ketones)
*basicity: 2°>3°>1°> NH3 (more groups, more basic) RCHO + Cu2+ R-COOH + Cu2O
*Heterocyclic Amines cyclic compounds that contain N (b)Tollen’s Test −rgnt: Ammoniacal AgNO3 (Silver
atom as part of the ring Nitrate) form Silver mirror w/
occur widely in biological systems Aliphatic & Aromatic Aldehyde
RCHO + Ag2+ R-COOH + Ag°
Classification based on the Group attached to N:
(c)Iodofrom Test reaction w/ I2 – K2 (test for
methylketones) yellow; fowl smell
1. Acetone used as a solvent for such products as paints,
3. Reduction to Alcohols
lacquers, & cellulose acetate because of its miscibility with both
4. Addition of Alcohols/ Acetals Formation
5. Addition of Grgnard Reagents water & non polar
(a)Formaldehyde will give primary alcohols nail polisher remover
(b)Higher Aldehydes will give secondary alcohols 2. Testosterone makor constituent of the male sex hormone
(c)Ketones will give tertiary alcohols responsible for the development of the
(d)Esters will give tertiary alcohols secondary
sex characteristics
steroidal ketone
❖Important Aldehydes: 3. Muscone odorous principle component of musk (sex
attractants) valued for its ability to enhance fragrances even
1. Formaldehyde preservative for anatomical specimens when present in minute amounts
because it causes skin hardening present in many of the expensive perfumes as
effective disinfectant used in hospital fixative *Musk − natural substance w/ a strong sweet
embalming fluid –(FORMALIN) smell
creates a “silver mirror” on the walls of a test 4. Pheromones produce by musk to attracts sex ;
tube w/ Silve Nitrate (Scents) 5. Muscaline pheromone produce by house
2. Acetaldehyde intermediate in the manufacture or acetic, flies
ethyl acetate, vinyl acetate which in turn 6. Chloracetophenone lacrimator (irritates eye)
are used on is used as a Tear Gas (produce stinging pain
the production of synthetic rubber & water-based in the eyes &
paints. streaming from the
3. Chloral starting material for the manufacture of insectides eyes & nose)
-DDT *Chloral Hydrate “knockout drops” 7. Pipper spray contain capsaicin (sili)
dissolves Starch, Resins, Proteins 8. Acetophenone has been used as a hypnotic but newer &
metabolite: Trichloroacetic Acid safer drugs are now available
4. Butanal a constitutent of the aroma of fresh bread 5. 9. Methyl Ethyl Ketone (MEK) solvent for lacquers, paints, plastics
Benzaldehyde once called “Oil of Bitter Almond” because of
its presence in almond seed
used as Flavoring Agent
intermediate in the manufacture of drugs, dyes, &
other organic products Hydrocarbons with Carbonyl Functional Group
6. Cinnamaldehyde chief constituent of the oil of cinnamon -Carbonyl Group is a functional group composed of a
bark 7.Vanillin fragrant component of vanilla beans carbon atom double-bonded to an
flavoring agent oxygen atom.
8. Citral major component of lemon grass oil
Carboxylic Acids R-COOH/ Ar-COOH
terminal functional group
product of hydrolysis of anhydrides
product of further oxidation of Primary Alcohol
Ketones (RCOR) IUPAC: Parent chain has the –C=O ✧Nomenclature of Acids
group, Its is given the lower 1. Common name Uses Greek letters to indicate the
number positions of substituents
Change –e to –one C-C-C-C-C-COOH
product of oxidation of Secondary alcohol Alpha=next to COOH
non terminal functional group Beta
Example: Gamma
Propanone (acetone) Sigma
− a substrate can be Epsilon
used to synthesize Often derived from Latin Greek name indicating
tertiary alcohol the original source of the acid
− simplest Ketone 2. IUPAC Parent chain contains the –COOH, carboxy C
is #1 Change –e to –oic
Ex: methane? –methanoic acid
Butanone
✧Reactions: 1. Acid/ Salt Formation
-Other example: 2. Conversion into functional derivatives
Acetone used as a solvent & nail polisher remover (a) conversion into acid chlorides
Testosterone a male sex hormone, steroidal ketone (b) conversion into an ester
Muscone odorous principle of musk (sex attractants) (b) conversion into amides
Pheromones produce by musk to attracts sex ; (Scents) 3. Reduction
Muscaline pheromone produce by house flies
Chloracetophenone lacrimator (tear gas) ✧Kinds of Acids: (based on the number of carboxyl group
Pipper spray contain capsaicin (sili) –COOH) 1. Monocarboxylic acids saturated fatty acids,
Metabolism of Ketones: one carboxylic acid group
Ketones are very stable
Common Name # Systematic Name Formula
Primary route of metabolism: reduction to alcohol
C CnH2n+1COOH
❖Important Ketones:
Acid) Tetraenoic Acid (4 double bonds)
Formic Acid 1 Methanoic Acid HCOOH
▪ Arachidonic Acid(20:4Δ5,8,11,14)
(5,8,11,14-Eicosatetranoic Acid)
Acetic Acid 2 Ethanoic Acid CH3COOH
can be synthesized through the bne
Propionic Acid 3 Propanoic Acid CH3CH2COOH *Palmitoleic, Oleic, Linolenic,Linoleic & Linolenic
are the most abundant unsaturated fatty acids in
Butyric Acid 4 Butanoic Acid CH3(CH2)2COOH animal lipids
*Linoleic, Linolenic, Arachidonic
Valeric Acid 5 Pentanoic CH3(CH2)3COOH are the three essential fatty acids
*Omega refers to VH3 Methyl group
Caproic Acid 6 Hexanoic Acid CH3(CH2)4COOH *Fatty Acids are aliphatic carboxylic acids
occur mainly as esters in natural fats & oils but do
Caprylic Acid 8 Octanoic Acid CH3(CH2)6COOH not occur in the unsterified from as free fatty acids,
a
Capric Acid 1 Decanoic Acid CH3(CH2)8COOH transport form found in the plasma.
0 are usually straight-chain derivatives containing an
even number of carbon atoms.
Lauric Acid 1 Dodecanoic Acid CH3(CH2)10COOH the chain may be saturated or unsaturated
2
❖Important Acids:
Myristic Acid 1 Tetradecanoic Acid CH3(CH2)12COOH 1. Salicylic Acid Monoprotic Acid
4 used for treatment of fungal infection & removal of
warts & corns
Palmitic Acid 1 Hexadecanoic Acid CH3(CH2)14COOH used as a keratolytic agent (for the removal of
6 dead skin cell)
* Whitfield’s Ointment ® (antifungal)
Stearic Acid 1 Octadecanoic CH3(CH2)16COOH = Benzoic Acid + Salicylic Acid
8 Acid 2. Acetylsalicylic Acid (ASPIRIN)
analgesic, antipyretic, treatment of colds,
Arachidic Acid 2 Eicosanoic Acid CH3(CH2)18COOH headache, minor aches & pains
0 3. Acetaminophen USP(Paracetamol BP) substitute for
aspirin 4. Citric Acid found in citrus fruits
Behemic Acid 2 Docosanoic Acid CH3(CH2)20COOH Triprotic Acid
2 5. Lactic Acid foud in sour milk
formed during fermentation of milk sugar,
Lignoceric 2 Tetracosanoic Acid CH3(CH2)22COOH lactose, & responsible for souring of spoiled
Acid 4 milk
product of fermentation milk sugar
6. Tartaric Acid found on several fruits particularly
grapes salt of tartaric acid
Diprotic Acid
2. Dicarboxylic Acids saturated acids with two –COOH group *Potassium Hydrogen Tartarate (Cream of Tartar)
3. Others −used in making baking powder
Monobasic/ Monoenoic Acid/ Monocarboxylic acid *Potassium Sodium Tartrate −used as a mild cathartic
unsaturated fatty acids, with one double bond 7. Benzoic Acid Monoprotic Acid
▪ Palmitoleic Acid (16:1Δ9) contains 16C w/ 1 double used as Antifungal Agent
bond (cis-9-hexadecanoic its sodium salt, sodium benzoate,
acid) −is used as a food preservative
▪ Oleic Acid (18:1Δ9) at position between 9&10 8. Para-aminobenzoic Acid used in suntan lotions to prevent
(cis-9-octadecanoic acid) the dangerous UV rays from reaching the skin
▪ Elaidic Acid (18:1Δ9) (trans-9-octadecanoic Acid) 9. Acetic Acids vinegar, spermatocidal
▪ Nervonic Acid (20:1Δ15) (cis-15-tetracosanoic Acid) considered as a universal precursor for fatty acids,
lipids, & other organic plant products
Polyunsaturated (Polyethanoid; Polyenoic Acid) *Glacial Acetic Acid Ethanolic Acid
Dienoic Acids (2 double bonds)
▪ Linoleic Acid (18:2Δ9,12) (9,12-octadecanoic Acid)
Trienoic Acid (3 double bonds)
▪ Linolenic (18:3Δ9,12,15) (9,12,15-ocatadecatrienoic
4 Succinic Acid
#C Name
5 Glutaric Acid
2 Oxalic A
6 Adipic Acid
3 Maloni
7 Pimetic Acid
*Azelaic acid
8 Subericanti-pimple
9 Azelaicoh
my
10 Sebacicsuch good apple
pie
sweet as
sugar
Ex:
Ethanoyl chloride
(acetyl chloride)
Reactions: Hydrolysis (requires an acid catalyst & heat ORGANIC MEDICINAL CHEMISTRY
products are Carboxylic Avid &
Ammonia Gas) Organic Medicinal Chemistry Physicochemical properties of a drug that
affect its biological action.
-oic acid amide the practice of medicinal chemistry is
devoted to the discovery & development
of new drugs
Example: Drug an agent intended for use in the diagnosis, mitigation, treatment,
-Ethanamide: cure, or prevention of disease in humans or another animals Receptor
a substance to which a drug needs to interact with to elicit a
pharcological response
-N-methylethanolamide: Affinity ability of a drug to bind to the receptor
Intrinsic ability of a drug to exert a pharmacologic
action Four Fundamental Pathways:
1. Absorption
2. Distribution
3. Metabolism
4. Excretion: Glomerular Filtration
Active Tubular Secretion
Passive tubular –reabsorption
Enterohepatic Recirculation drugs emptied via the bile duct
into the small intestine can be
reabsorbed in the intestinal lumen
back to the systemic circulation
(LIver intestines Liver) (c) Thermodent® Formaldehyde USP (formalin)
disinfectant; embalming fluid
Isosterism describes the selection of structural components, the steric contains not less than 37% of formaldehyde
electronic & solubility characteristics of a drug which make it w/ methanol added to retard polymerization
interchangeable with drugs of the same pharmacologic class MOA: Direct & nonpecific alkylation of
nucleophilic functional groups of
Isosteres compounds or groups of atoms having the same number & proteins
arrangement of electrons (d) Cidex® Glutaraldehyde/ Glutarol
group of atoms that impart similar physical & chemical sterilizing solution for equipment & instruments
properties to a molecule, because of similarities in the size, that cannot be autoclaved
electronegativity, or stereochemistry II. Phenols (Carbolic Acid)
compounds may be altered by isosteric replacements of standard to compare germicide
atoms or groups, to develop analogues with select biologic was introduced as a surgical antiseptic
example: replacement of the hydroxyl group of folic acid by by Sir Joseph Lister
an amino group. antiseptic; disinfectant
Liquefied Phenol, USP (phenol containing 10% water)
Phenol Coefficient ration of the dilution of a
disinfectant to the dilution of phenol
required to kill S. typhi.
the greater the Phenol Coefficient,
the greater the Antibacterial property.
Local Anti- Infectives or Germicides
SAR substitution of alkyl, aryl, halogen at
Antiseptic compounds that kill (−cidal) or prevent the growth of p− position increase antibacterial property.
(–static) microorganisms when applied to living tissue
Straight chain alkyl group
Disinfectant agents that prevent infection by the destruction of
are > than branches
pathogenic microorganisms when applied to inanimate
Phenol for Protein precipitation
objects
Cresol a mixture of three isomeric cresols
I. Alcohol & Related Compounds
Eugenol clove oil
# of carbons, antibacterial property
toothache drop
(but up to carbon 8 only)
anesthetic; antiseptic
branching tend to Antibacterial property
Thymol metacresol (m-cresol)
(except to isopropyl)
antifungal; used for the treatment of tinea inf.
(a) Alcohol USP (Spiritus vini recticatus)
Resorcinol CRH (Dihydroxy benzene)
”Grain Alcohol”; “wine spirit”
antiseptic; keratolytic
the most widely abused of all recreational drugs.
OH (Cathecol) / (o-hydroxyphenol)
undergo a series of Oxidation reaction in vivo
manufacture from:
Fermentation of grain OH (Resorcinol) / (m-hydroxyphenol)
Hydration of Ethyl OH (Hydroquinone) / (p-hydoxyphenol)
Denatured Alcohol
ethanol that has been rendered unfit for use in
intoxicating beverages by the addition of other
substances
completely denatured alcohol contains added III. Oxidizing Agents
methanol (wood alcohol) & benzene & is Primary Mechanism of Action:
unsuitable for either internal or external use 1. Liberation of nasent oxygen (nasent alone)
Diluted Alcohol 49/50 % -Free radical
Rubbing Alcohol 70% 2. Denature of Proteins
Absolute Alcohol 95%
Dehydrated Algohol 99% Panoxyl® (Hydrous Benzoyl Peroxide) -2.5%, 5%, 10%
Isopropy alcohol primarily used to disinfect the skin & −Keratolytic & keratogenic agent
surgical instruments −MOA: Induces proliferation of epithelial cell
rapidly bactericidal in the −Increases cell turnover
concentration range of 50% to 95%
a 40% concentration is considered to − most effective topical OTC agent for the control of acne
be equal in antiseptic power to a Carbamide Peroxide a stable complex of urea & hydrogen
60% ethanol concentration peroxide
Formic Acid blindness releases hydrogen peroxide when mixed
Ethanol act competitive inhibition w/ water
(b) Ethylene Oxide gas sterilant Hydrogen Peroxide particularly active against anaerobic
used to sterilized temperature-sensitive bacteria & find use in the cleansing of
medical equipment & certain contaminated wounds.
pharmaceuticals that cannot be effectiveness is somewhat limited by its
autoclaved poor tissue penetrability & transient
MOA: alkylation of functional groups in action
nucleic acids & proteins the stability is increased in Acid Medium
carcinogenic *Hydrogen Peroxide (0.03%) has Acetanilide to
increase its stability by
catalytically retarding its Iodides only ion that used for expectorant in cough
decomposition syrup
*Vincent’s Stomatitis (Hairy Tongue) result in 2nd bet expectorant (next to Water vapor)
continued use of Iodophor complexes of iodine
Hydrogen Peroxide as & nonionic surfactants
mouthwash such complexes retain the germicidal
*Volume Specifications: mL of Oxygen measured at properties of iodine & also reduce its
standard temperature & volatility & essentially remove its irritant
pressure. Thus, a 20- properties
volume solution is 6% & PVP : non-ionic Surfactant complexes of I2
has 20mL oxygen Less irritating
More washable
Less volatile I2
M.O.A : Iodination of amide in CHON &
IV. Halogen-containing Compounds oxidation of –SH group
a. Chlorine (Cl) NaOCl bleaching agent V. Cationic Surfactant (cationicpositive charge)
Halazone water disinfection → Refers to quaternary ammonium component
M.O.A : chlorination of amide in CHON & → Have surface active property
oxidation of –SH group −Causes absorptioninto the cell wall
Halazone chlorine-containing −Causes distortion of the cell (lysis)
used to disinfect drinking water a. Benzalkonium Chloride used as detergent, emulsifying, &
Chlorides may be precipitated from solution by the Silver wetting agent
Nitrate reagent used w/ parabens as a preservative
b. Iodine (I) one of the oldest known germicides in use today is germicidal surfactant which render
produces blue color w/ Starch & Dextrin inactive in the presence of Soaps
Iodine preparations official in USP: Sodium Lauryl Sulfate deactivate the
- Iodine Tincture (2% solution of iodine in cationic surfactant
50% alcohol w/ NaI) VII. Heavy metals
-Strong Base (Lugol’s Solution)- (5% I in water w/ KI) w/ Oligodynamic Properties
-Iodine Solution (2% iodine in water w/ NaI) has few concentration, they are able to inhibit
*Sodium & Potassium iodine Stabilizer microorganisms
Povidone Iodine (Betadine ®) a. Ag AgNO3 −for ophthalmia neonatorum
used as an antiseptic for skin application −may cause conjunctivitis
before surgery & injection New alternative: Erythromycin Ointment
a complex w/ the nonionic surfactant Ag Sulfadiazine (Flammazine®)
polymer, Polyvinylpyrrolidone − burn ointment
has 10% Iodine (approximately) b. Hg quicksilver
a water-soluble complex that release MOA: reacts with sulfhydryl (SH) groups in enzymes &
Iodine Slowly
other proteins
provides a nontoxic, non-irritating,
nonvolatile & nonstaining form of Iodine
Span − w/o Tween − o/w nonionic compounds such as Cysteine & DImercaprol
this is reversible by thiol-containing
is also used a 1% to 3% solution for the treatment
b. Methyl benzythonium Chloride: Diaperene® of tinea & yeast infections
for Diaper rash also used orally as an antihelminthic for
Cause by Bacterium ammoniagenesis strongyloides & oxyuriasis
(causes liberation of ammonia in b. Basic Fuchsin ingredient of Carbol-fuchsin solution
decomposed urine) (Castellani’s paint), used topically in the
liberates ammonia from treatment of fungal infections, such as
decompose wine ringworm & athlete’s foot
c. Cetyl Pyridinium Chloride c. Methylene Blue antidote for Cyanide Poisoning
used as a general antiseptic in high concentrations, it promotes the
available form: Throat lozenges & mouthwashes conversion of hemoglobin to
FDA approved for the treatment of Gingivitis Methemoglobin, which because of its high
d. Chlorhexidine (Bactidol®) affinity for cyanide ion diverts it from
used as irrigation solution & as mouthwash inactivating hemoglobin
not absorbed through skin or mucus membrane & in low concentration, it is used to treat
does not cause systemic toxicity drug0induced methemoglobin
e. Hexidine mouthwah Hg1Cl2 Calomel (Mercurous Chloride)
HgCl2 Corrosive sublimate (Mercuric Chloride)
Ammoniated mercury White precipitate;
used for skin infections
VI. Dyes (cationic) positively charge Organic Mercurials: Merthiolate (Thimerosal)
Effective against gram (+) & fungi preservative for vaccines
a. Gentian Violet (Methyl Violet)/ (Crystal Violet) MOA: reaction w/ -SH of CHON
(p-rosanilline)
Vaginal suppository (Anti-candida, yeast infection) Chlormerodin Hg-197 used for scintillation
Helminths (Strongyloides spp.) scanning of brain for
suspected tumors b. Nystatin (Mykinac®, Mucostatin®, Nilstat®)
Polyene Antifungal: binds to ergosterol,
VIII. Preservatives resulting in holes/ pores in the
used to prevent microbial contamination fungal cell membrane
IDEAL CHARACTERISTICS: effective at low the aglycon portion of nystatin consisting of
concentration against all possible 38-membered ketone ring w/ a single tetracene & diene
microorganisms, notoxic, compatible w/ other chromophores isolated from each other by a methylene
constituents used in the preparation, stable for group, one
the shelf life of the preparation carboxyl, one keto & eight hydroxyl groups
a. Paraben (esters of p-hydroxy benzoic acid) Use: Candidiasis of Esophagus/GIT
for liquid dosage form
antifungals C. Topic Azoles
preservative effect tends to increase w/ molecular MOA: Inhibition of c14 lanosterol demethylase
weight Lanosterol Ergosterol
Methylparaben molds Inhibition of ergosterol synthesis
Propylparaben yeasts
more oil-soluble so it is prepared for oils & Imidazole
fats
Butylparaben cause endocrinologic abnormalities Clotrimazole
b. Chlorobutanol employed as a bacteriostatic agent in
pharmaceuticals for injection, Toconazole
ophthalmic
use & intranasal administration Miconazole :
c. Benzyl alcohol for dermal/ topical preparation
commonly used as a preservative in vials of Triazole
injectable drugs in concentrations of 1% to
4% in water or saline Fluconazole
d. Benzoic Acid for topical preparation
Very effective in acidic pH/low pH
Itraconazole
e. Sorbic Acid for sugar-containing preparation like elixir
an effective antifungal preservative
Ketoconazole
Syrup, NF self-preserving
Antifungal Agents:
General MOA: inhibition of ergosterol; synthesis injury to cell membrane
Amphotericin B (Fungitone®) S.nodosus
II. AGENTS FOR LESS SERIOUS SYSTEMIC MYCOSES
a. Ketoconazole
Nystatin (Mycostatin ®) S.norsei by
potent enzyme inhibitor
Hazen&Brown
Inhibits testosterone antiandrogenic effects
gynecomastia
Natamycin (Natacin®) S. natalensis low sperm count
low libido
Griseofulvin P. griseofulvin b. Fluconazole preferred for resistant candidiasis
has excellent penetrability into the CSF
C. Itraconazole
2nd best systemic antifungal next to Amphotericin B
lacks the endocrinologic effects of ketoconazole
Fatty Acidsall fatty acids & their salts have fungicidal properties Uses: Blastomycosis
a. Propionic Acid present in sweat in low concentrations (around Histoplasmosis
0.01%) Paracoccidioidomycosis
b.Undecylenic Acid obtained from the destructive distillation Coccidiodomycosis
of Castor Beans (Ricinus communis) III. AGENTS FOR SERIOUS SYSTEMIC MYCOSES
I. AGENTS FOR SUPERFACIAL MYCOSES a. Amphotericin B
a. Griseofulvin (P. griseofulvin) Gold Standard, Best organ, DOC
No established MOA: Inhibitor of microtubule Polyene antifungal creates pores in fungal cell
assembly (antimitotic) membrane
accumulates in the stratum corneum of the skin, acts Side Effects: Revesible Azotemia (former name of
as a protective barrier uremia) Patient should be monitored (BUN,
is recommended for the systemic treatment or Creatinine
refractory ringworm infections Clearance)
is supplied in “microsize’” & “ultramicrosize” forms Febrile Reaction
its bioavailability is notoriously poor Anemia
is used in the treatment of Tinea corpuris, tinea Thrombophlebitis
unguium, Tinea capitis, & tinea pedis, caused by various b. Itraconazole
species of C. Caspofungin inhibits 1-3 β-glucan synthase
dermatophyte fungi, including Trichophyton,
Microsporum, & Epidermophyton. glucan (cell wall)
is very lipophilic compound w/ vey low water d.Voriconazole
solubility higher BA w/ ingestion of fatty foods e.Flucytosine inhibits thymiditate synthase
Uses: Ringworm Infections
by replacing uracil in nucleic acid always given w/ Amphotericin B for the treatment of
synthesis (DNA&RNA) systemic mycoses & meningitis caused by
d. Terbinafine e. Naftifine allylamine, inhibition of squalene epoxidase Cryptococcus neoformans & candida
1. For Superficial
Mycoses ∙ Griseofulvin
Kanamycin Streptomyces kanamyceticus
∙ Nystatin Grisactin®, Grifulvin,V®, Fulvicin®
∙ Clotimoxazole
Clavulanate S. clavuligerus
∙ Miconazole Mycostatatin®, Nilstat®
Erythromycin S. erythreus ∙ Econazole
∙ Oxiconazole Lotrimin®
Griseofulvin P. griseofulvin ∙ Sulconazole
∙ Ketoconazole Monistat®, Micatin®
Polymixin B. polymixa ∙ Butenafine
Spectazole®
∙ Haloprogin
Bacitracin Bacillus subtilis ∙ Terbinafine
Oxistat®
∙ Ciclopirox
Nystatin S. noursei by Hazen & Brown ∙ Naftipine Exelderm®
∙ Whitfield’s ointment
Chloramphenicol S. venezuelae ∙ Salicylic acid Nizoralv®
∙ Tolnaftate
Cephalosporins Acremoium Chrusogenum
∙ Selenium sulfide Mentax®
2. For Less Serious
Aztreonam Chromobacterium violaceum
Systemic Mycoses Halotex®
∙ Ketoconazole
Chlortetracyclin S. aureofaciens
∙ Fluconazole Lamisil®
Linezolid E. faecium ∙ Itraconazole
3. For Serious Systemic Penlac®
Ivermectin S. avemitilis Mycoses
∙ Amphotericin B Naftin®
LIncomycin S. lincolnensis
∙ Itraconazole
Carbapenems: Thienamycin S. cattleya ∙ Caspofungin
∙ Vorconazole
Rifampicin S. mediterranei ∙ Flucytosine
Amphotericin B S. nodosus
Daptomycin S. roseosporus
Lithium (Li) Carmine Red Purple
INORGANIC CHEMISTRY
Flame Test: Groups of Cation:
Radiopharmaceutical Uses
I Cl AgCl -(white) No ppt.
Br AgBr -(cream) Technetium 99m−Phytate −Liver imaging & potency studies
I AgI -(yellow) Technetium −Kidney imaging,
insoluble in HNO3 99m−Heptagluconate −determining renal function
Unknown Tests
Acetate C2H3O2Sulfuric acid+ ethanol fruity odor of ethyl acetate
Ferric chloride TS brownish red or reddish brown ppt of basic acetates
Aluminum Al Ammonium TS gelatinous ppt. w/c dissolves in excess of ammonium TS
Aluminon reagent red lake
Ammonium Acidic cobalt solution intense blue colored complex at interfeface Co(CNS)4
NH4SCN Ferric salts blood red ferric thiocyanate
Thiocyanide
Arsenites AsO3 Silver Nitrate test yellow ppt soluble in nitric acid
Magnesia Mixture no reaction (differentiating test for arsenates & arsenite)
Chloride Cl Silver nitrate test white curdy precipitate ppt soluble in ammonia, insoluble in nitric acid
Chromium Cr Sodium hydroxide grayish green slug dissolves in excess reagent (turn to yellow upon addition of Na
Peroxide)
Cobalt Co Sodium hydroxide blue ppt of CO(OH)2 (boiling) olive green rose red
Potassium nitrite + acetic acid Fernando Gabriel Reyes yellow ppt
α-nitroso-β-naphthol brown ppt soluble in HCl
Silver Ag HCl white curdy ppt. insoluble in nitric acid but soluble in ammonia
Saccharin (Fluorescein Test)- Resorcinol+ sulfuric acid + excess NaOH Fluorescent green liquid
Common Names of Inorganic Compounds
Ammonia water Ammonium Hydroxide Solution NH4OH Carbolic Acid Phenol (C6H5OH)
Agua Fortis Conc. Nitric Acid HNO3 Cane Sugar Sucrose (C12H22O11)
Agua Regia Mixture of Conc. Nitric Acid & Hydrochloric Acid HNO3/ 3HCl Marsh Gas Methane (CH4)
Amiodarone
PABA (Para-aminobenzoic Acid)
− used as Ultraviolet sunscreen
− enhancer of Serum Salicylate
− should not be taken concurrently w/ sulfonamides because it
interferes w/ the Antimicrobial Activity of the latter
Sulfonamides − are assayed by using NaNO2 & KI
Penicillin
72 96 109 268
60 84
73 97 110
61 85
98 111 272
62 74 86
99 112
63 75 87
100 113
64 76 88
101
65 77 89 114
102
78 91 115
66 104
79 116
67 90 103
117
80 105
68 93
118
81 106
69 92
107
82
70 95
1 1.0079 HydrogenH
2 4.0026 Helium He
3 6.941 Lithium Li
4 9.0122 Beryllium Be
5 10.811 Boron B
6 12.0107 Carbon C
7 14.0067 Nitrogen N
8 15.9994 Oxygen O
9 18.9984 Fluorine F
10 20.179 Neon Ne
7
11 22.989 Sodium Na
7
12 24.305 Magnesium Mg
13 26.981 Aluminum Al
5
14 28.085 Silicon Si
5
15 30.973 Phosphorus P
8
16 32.065 Sulfur S
17 35.453 Chlorine Cl
19 39.098 Potassium K
3
18 39.948 Argon Ar
20 40.078 Calcium Ca
21 44.955 Scandium Sc
9
22 47.867 Titanium Ti
23 50.941 Vanadium V
5
24 51.996 Chromium Cr
1
25 54.938 Manganese Mn
26 55.845 Iron Fe
28 58.693 Nickel Ni
4
27 58.933 Cobalt Co
2
29 63.546 Copper Cu
30 65.39 Zinc Zn
31 69.723 Gallium Ga
32 72.64 Germanium Ge
33 74.921 Arsenic As
6
34 78.96 Selenium Se
35 79.904 Bromine Br
36 83.8 Krypton Kr
37 85.467 Rubidium Rb
8
38 87.62 Strontium Sr
39 88.905 Yttrium Y
9
40 91.224 Zirconium Zr
41 92.906 Niobium Nb
4
42 95.94 Molybdenum Mo
43 98 Technetium Tc
44 101.07 Ruthenium Ru
45 102.905 Rhodium Rh
5
46 106.42 Palladium Pd
47 107.868 Silver Ag
2
48 112.411 Cadmium Cd
49 114.818 Indium In
50 118.71 Tin Sn
51 121.76 Antimony Sb
53 126.904 Iodine I
5
52 127.6 Tellurium Te
54 131.293 Xenon Xe
55 132.905 Cesium Cs
5
56 137.327 Barium Ba
57 138.905 Lanthanum La
5
58 140.116 Cerium Ce
Iodine I2
Phosphorus wite P
Sodium fluoride NaF
Potassium antimonate(pyro) KSb(OH)6
Sodium hydrogen phosphate Na2HPO4
Potassium biiodate KH(IO3)2
Sodium hydrogen sulfate NaHSO4
Potassium bisulfate KHSO4
Sodium hydrogen sulfite NaHSO3
Potassium bisulfite KHSO3
di-Sodium hydrogenphosphate Na2HPO4.2H2O
Potassium bromate KBrO3
Sodium iodate NaIO3
Potassium bromide KBr
Sodium iodide NaI
Potassium chlorate KClO3
Sodium meta-periodate NaIO4
Potassium cyanate KCN
Sodium methaborate NaBO2.2H2O
Potassium dihydrogen phosphate KH2PO4
Sodium perchlorate NaCl3O4
Potassium disulfate(pyrosulfate) K2S2O7
Sodium peroxide Na2O2
Potassium ferro(III)cyanide K4Fe(CN)6
Sodium persulfate Na2S2O8
Potassium metabisulfite K2S2O5
Sodium polyphosphate (NaPO3)12-13.Na2O
Potassium nitrate KNO3
Sodium pyrophosphate Na4P2O7
Potassium nitrite KNO2
Sodium silicate Na2Si3O7
Potassium perchlorate KClO4
Sodium sulfate Na2SO4.10H2O
Potassium persulfate K2S2O8
Sodium sulfite Na2SO3
Potassium phosphate monobasic KH2PO4
di-Sodium tetraborate Na2B4O7
Potassium pyrophosphate K4P2O7
Sodium tungstate Na2WO4.2H20
Potassium selenocyanate KSeCN
Stannic chloride SnCl4
Potassium thiocyanate KSCN
Stannous chloride SnCl2
Selenium metall Se
Stannous chloride SnCl2.2H2O
Silicic acid SiO2.aq
Stannous fluoride SnF2
Silver nitrate AgNO3
Stannous oxide SnO
Silver sulfate Ag2SO4
Strontium carbonate SrCO3
Silver sulfate Ag2SO4
Thallium wire Tl
Sodium bismuthate NaBiO3
Thallous nitrate TlNO3
Tin Sn Zinc carbonate ZnCO3
Zinc Zn
+1 +2 +3 +4 ous ic
H Ba Al C ANTIMONY Sb +3 +5 ARSENIC As +3 +5
Li Ca B Si BISMUTH Bi +3 +5 CHROMIUM Cr +2 +3
K Bd Fe COBALT Co +2 +3 COPPER Cu +1 +2 GOLD Au
Na Mg Cr +1 +3 IRON Fe +2 +3 LEAD Pb +2 +4
Ag Ra Ni MANGANESE Mn +2 +4 MERCURY Hg +1 +2
Cu Sr Co NICKEL Ni +2 +3 NITROGEN N +3 +5
Zn Bi PHOSPHORUS P +3 + 5
Cu As PLATINUM Pt +2 + 4 TIN Sn +2 + 4
Fe Sb
Pb
Hg
Ni
Co
Cd
Mn
Sn
-1 -2 -3 -4
Br O As C
Cl S N Si
FP
H
I
IV.Common Radicals
-1 BROMIDE Br CHLORATE ClO3 CHLORIDE IODATE IO3 IODIDE I METABORATE BO2
ACETATE C2H3O2 ALUMINATE Al(OH)4 Cl CYANATE CNO FLOURIDE F MEATAPHOSPHATE PO3 NITRATE NO3
BICARBONATE HCO3 BROMATE BrO3 HYDROXIDE OH HYPOCHLORITE ClO NITRITE NO2 PERCHLORATE ClO4
PERMANGANATE MnO4 THIOCYANATE
SCN
-2
CARBONATE CO3 CHROMATE CrO4
DICHROMATE Cr2O7 MANGANATE
MnO4 MOLYBDATE MoO4 OXALATE
C2O4 OXIDE O PEROXIDE O2
HYDROPHOSPHATE HPO3 SILICATE SiO3
SULFATE SO4 SULFIDE S SULFITE SO2
STANATE SnO3 TARTRATE C4H4O6
TETABORATE Br4O7 THIOSULFATE S2O3
ZINCATE ZnO7
-3
ARSENATE AsO4
ARSENITE AsO3
BORATE BO3
CITRATE C6H5O2
FERICYANIDE Fe(Cn)6
PHOSPHATE PO4
PHOSPHITE PO3
PY
PY
OR
AM
CO
M