Oxytetracycline: Eric Scholar

Oxytetracycline
Eric Scholar University of Nebraska Medical Center, Omaha, USA

ã 2007 Elsevier Inc. All rights reserved.
Introduction
Oxytetracycline is a first-generation tetracycline that is used sparingly today. Its mecha-

nism of action, pharmacokinetics, therapeutic uses, and adverse effects are similar to other
first-generation tetracyclines.
Nomenclature
Name of the Oxytetracycline HCL
Clinical Form
Related Names Abbocin; abbocin tablets; berkmycen; berkmycen syrup; biomycin
Source: c; biostat; cyclomicine; cyelindif; dabicycline; dophacycline;
EMTREE dumocyclin(a); embacycline; fanterrin; geomycin; 5
hydroxytetracycline; hydroxytetracycline; ia loxine; ia oxin;
imperacin; italecyclina; liquamycin; liquamycin la; liquamycin la
200; macocyn; medamycin; neo tetrine; nsc 9169; ossitetra; otc;
oxatets; oxlopar; oxtetracyline; oxycycline; oxy dumocyclin;
oxyject 100; oxymycin; oxymykoin; oxypan; oxyterracin;
oxyterracine; oxyterracyna; oxytet; oxytetracid; oxytetracyclin;
oxytetracycline hydrochloride; oxytetramycin; oxytetravet;
oxytetrine; quiervetin; riomitsin; ryomycin; stevacin; terrafungine;
terralon; terramycin; terramycine; terravenoes; terravenos;
tetrabion; tetramel; tetran; tetravet; toxinal; ultramicina;
unimycin; ursocyclin; vendarcin; vendracin; Oxytetracycline;
Tetramycin; Terramycin (trade); abbocin
Chemical Names 4-dimethylamino-1,4-4a,5,5a,6,11,12a-octahydro-
3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-
naphthacenecarboxamide.
CAS Number 79-57-2
Basic Chemistry
Chemical Structure
Structure
1
2 Oxytetracycline
Chemical Formula C22 H24 N2 O9

Properties
Physical Properties Oxytetracycline is a pale yellow to tan odorless crystalline
powder.
Molecular Weight 460.437
Solubility 1 g of oxytetracycline is soluble in 4150-ml water, 100-ml alcohol,
and in over 10,000-ml chloroform.
Ionization Constant
Value Salt Conditions Reference Comments
pKa 3.3 Hansch et al (1990)
Human Pharmacokinetics
Oxytetracycline is moderately well absorbed from the upper gastrointestinal tract, with
food decreasing plasma levels by approximately 50%. Although widely distributed
throughout the body, it attains lower concentrations overall than second-generation
tetracyclines. Passage into the cerebrospinal fluid is minimal. Small amounts of oxytetra-
cycline are metabolized by the liver, with approximately 60% of an administered excreted
in the urine. The half-life of oxytetracycline is prolonged in renal insufficiency.
Pharmacokinetic Properties
Prep. and
Route of
Value Units Admin. Reference Comments
Absorption Approximately 75% of oxytetracycline is absorbed orally.

Bioavailability
Distribution
Volume of Distribution
Plasma Protein Binding 20-35 % Finch (1997)
Metabolism
Plasma Half-Life 9 hr Finch (1997)
Bio Half-Life
Clearance 1.5 mg/ml Finch (1997) 60–70% of oxytetracycline
is excreted unchanged
in urine.
Routes of Elimination
Targets-Pharmacodynamics
Oxytetracycline, like other tetracyclines, inhibits bacterial protein synthesis. It binds

principally to the 30S ribosomal subunit and specifically inhibits the enzyme-binding of
aminoacyl-t-RNA to the ribosomal acceptor site. At higher concentrations of oxytetracy-
cline, mammalian protein synthesis is inhibited as well.
Target Name(s):
30S ribosomal subunit.
Oxytetracycline 3
Therapeutics
The indications for oxytetracycline are similar to those for other first-generation tetra-
cyclines. It offers no therapeutic advantages over other members of this class, although it is
one of the least expensive preparations.
Indications
Prep. and Route

Value Units of Admin. Reference Comments
Nonspecific urethritis
Dosage 250 mg QID for periods of Grimbel and
4 days (p.o.) Amarasuriya
(1975)
Urinary Tract Infections
Dosage 250 mg QID (p.o.) Stamey et al (1974)
Syphilis
Dosage 30-40 gms. In divided doses Micromedex, http://
over a 1-15 day www.preceptor.
period (p.o.) com/
Brucellosis
Dosage 500 mg QID for 3 weeks Micromedex, http://
(p.o.) www.preceptor.
com/
Contraindications
Oxytetracycline is contraindicated in those known to be hypersensitive to tetracyclines.
The tetracyclines are usually contraindicated during pregnancy and breast feeding, and in
children younger than 8 years of age.
Adverse Effects
Side effects associated with oxytetracycline include aplastic anemia, thrombocytopenic
purpura, neutropenia, hemolytic anemia, thrombocytopenia, hypoglycemia, nausea,
vomiting, diarrhea, esophageal ulceration, renal failure, hepatotoxicity, photosensitivity,
rashes, and tooth discoloration.
Agent-Agent Interactions
Agent Name Mode of Interaction

Calcium, magnesium- and aluminum- Impair the absorption of the tetracyclines (up to 90%).
containing antacids
Ferrous salts Impair the absorption of the tetracyclines.
Sodium bicarbonate and cimetidine Impair the absorption of the tetracyclines.
Methoxyflurane anesthesia May cause renal failure after tetracycline use.
Penicillin Tetracyclines may interfere with bactericidal action of
penicillin
Oral contraceptives Tetracyclines may reduce levels of conjugated estrogen.
Bismuth subsalicylate Impairs the absorption of tetracyclines (30-50% reduction)
Cisatracurium Some antibiotics, including the tetracyclines, may
enhance the neuromuscular blocking effect of
cisatracurium.
4 Oxytetracycline
Rapacuronium Some antibiotics, including the tetracyclines, may

enhance the neuromuscular blocking effect of
rapacuronium.
Dicumarol Tetracycline therapy reduces plasma prothrombin activity,
increasing the risk of bleeding.
Isotretinoin An increased incidence of pseudotumor cerebri has been
reported in patients receiving isotretinoin in combination
with minocycline or tetracycline. This is due to an
additive toxicity when the drugs are given together.
Warfarin Tetracyclines reduce plasma prothrombin activity.
Porfimer There may be increased photosensitivity reactions due to
the additive effects of oxytetracycline and porfimer.
Pre-Clinical Research
The spectrum of activity of oxytetracycline is similar to that of tetracycline. In general,

oxytetracycline is slightly less effective than other tetracyclines against most common
pathogenic bacteria. Tetracyclines are active against most gram-positive bacteria includ-
ing Staphylococcus epidermidis and other staphylococci. Gram-positive bacilli such as Bacillus
anthracis are also sensitive. Several gram-negative organisms are also sensitive to oxytet-
racycline including Enterobacteriaceae such as Escherichia coli and the Enterobacter. Several
gram-negative bacteria that were sensitive to oxytetracycline in the past are now resistant.
These include Neisseria meningitides, Haemophilus influenzae, and others. Other sensitive
organisms include Mycoplasma pneumoniae, Rickettsia, Chlamydia, Spirochetes, Entamoeba,
and PlasmodiaKucers et al (1997), Finch (1997).
Other Research
Oxytetracycline is available commercially from Sigma Chemical Company (catalog
#75965) (www.sigmaaldrich.com).
Other Information – Web Sites
http://library1.unmc.edu:2048/login?url=http://www.preceptor.com/mdxcgi/
mdxhtml.exe?&tmpl=hcssrch1.tm1&SCRNAME=hcssrch1&CTL=d:/mdx/mdxcgi/
megat.sys, micromedex general drug information
http://www.medscape.com/druginfo, general drug information
http://www.fda.gov/cder/drug/default.htm fda site, general drug information
Journal Citations
Stamey, T.A., Fair, W.R., Timothy, M.M., et al. 1974. Serum versus urinary antimicrobial concentrations in
cure of urinary-tract infections. NEJM, 291, 1159–1163.
Grimbel, A.S., Amarasuriya, K.L., 1975. Nonspecific urethritis and the tetracyclines. Br. J. Venereal Dis., 51,
198–205.
Book Citations
Finch, R.G., 1997. Tetracyclines. O’Grady, F., Lambert, H.P., Finch, R.G., Greenwood, D. (Ed.), Antibiotic
and Chemotherapy, Edition 7, pp. 469–484, Churchill Livingstone, NY, NY.
Oxytetracycline 5
Hansch, C., et al. 1990. Hansch, C., et al. (eds.) Comprehensive Medicinal Chemistry, Edition Vol. 6. ,
Pergamon Press, NY.
Kucers, A., Crowe, S.M, Grayson, M.L., Hoy, J.F., 1997. Tetracyclines. The Use of Antibiotics. A clinical
review of antibacterial, antifungal and antiviraldrugs, Edition 5, pp. 719–762, Butterworth Heinemann,
Oxford, England.
Further Reading
Antibiotic and Chemotherapy, 7th ed., 1997

The Antimicrobial Drugs, 2nd ed., Scholar and Pratt, Oxford Univ. Press, 2000
Goodman and Gilman, The Pharmacological Basis of Therapeutics, 10th ed., McGraw-Hill, 2001
Antimicrobial Therapy and Vaccines, Yu et al., Williams and Wilkins, 1999.

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Oxytetracycline

Eric Scholar University of Nebraska Medical Center, Omaha, USA

Oxytetracycline is a first-generation tetracycline that is used sparingly today. Its mecha-

Chemical Formula C22 H24 N2 O9

Absorption Approximately 75% of oxytetracycline is absorbed orally.

Oxytetracycline, like other tetracyclines, inhibits bacterial protein synthesis. It binds

Prep. and Route

Agent Name Mode of Interaction

Rapacuronium Some antibiotics, including the tetracyclines, may

The spectrum of activity of oxytetracycline is similar to that of tetracycline. In general,

Other Information – Web Sites

Antibiotic and Chemotherapy, 7th ed., 1997

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