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L-AP4: Difference between revisions

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{{Short description|Chemical compound}}
{{drugbox
{{Drugbox
⚫
| IUPAC_name = (2S)-2-amino-4-phosphonobutanoic acid
| Verifiedfields = changed
| image = L-AP4_structure.png
| Watchedfields = changed
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| width = 200
| verifiedrevid = 451227757
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| CAS_number = 23052-81-5
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| IUPAC_name = (2''S'')-2-Amino-4-phosphonobutanoic acid
⚫
| ATC_prefix =
| image = L-2-amino-4-phosphonobutyric acid L-AP4.svg
⚫
| ATC_suffix =
⚫
| width = 200
⚫
| PubChem = 179394
⚫
| IUPHAR_ligand = 1443
| IUPHAR_ligand = 1412
⚫
| DrugBank =
⚫
| C=4|H=10|N=1|O=5|P=1
| molecular_weight = 183.099 g/mol
⚫
| smiles = OC(=O)C(N)CCP(O)(O)=O
⚫
| bioavailability =
⚫
| protein_bound =
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| metabolism =
⚫
| elimination_half-life =
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| excretion =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| pregnancy_category=
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| legal_status =
⚫
| routes_of_administration =
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}}


<!--Clinical data-->
'''L-AP4''' is a drug used in scientific research, which acts as a group-selective [[agonist]] for the group III [[metabotropic glutamate receptor]]s ([[Metabotropic glutamate receptor 4|mGluR<sub>4</sub>]]<sub>/</sub>[[Metabotropic glutamate receptor 6|<sub>6</sub>]]<sub>/</sub>[[Metabotropic glutamate receptor 7|<sub>7</sub>]]<sub>/</sub>[[Metabotropic glutamate receptor 8|<sub>8</sub>]]). It was the first ligand found to act as an agonist selective for this group of mGlu receptors,<ref>{{cite journal | pmid = 9251893 | author-separator =, | author-name-separator= }}</ref> but does not show selectivity between the different mGluR Group III subtypes. It is widely used in the study of this receptor family and their various functions.<ref>{{cite journal | pmid = 17581957 | author-separator =, | author-name-separator= }}</ref><ref>{{cite journal | pmid = 18035348 | author-separator =, | author-name-separator= }}</ref><ref>{{cite journal | pmid = 19017536 | author-separator =, | author-name-separator= }}</ref><ref>{{cite journal | pmid = 19481536 | author-separator =, | author-name-separator= }}</ref>
| tradename =
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category =
⚫
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status =
⚫
| routes_of_administration =


<!--Pharmacokinetic data-->
⚫
== References ==
⚫
| bioavailability =
{{reflist}}
⚫
| protein_bound =

⚫
| metabolism =
{{Glutamate_receptor_ligands}}
⚫
| elimination_half-life =
⚫
| excretion =


<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
⚫
| CAS_number = 23052-81-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = C8M58SS68H
⚫
| ATC_prefix =
⚫
| ATC_suffix =
⚫
| PubChem = 179394
⚫
| IUPHAR_ligand = 1410
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 156157
| synonyms = <small>L</small>-2-Amino-4-phosphonobutyric acid


<!--Chemical data-->
⚫
| C=4 | H=10 | N=1 | O=5 | P=1
⚫
| smiles = C(CP(=O)(O)O)[C@@H](C(=O)O)N
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DDOQBQRIEWHWBT-VKHMYHEASA-N
⚫
}}


'''L-AP4''' ('''<small>L</small>-2-amino-4-phosphonobutyric acid''') is a drug used in scientific research, which acts as a group-selective [[agonist]] for the group III [[metabotropic glutamate receptor]]s ([[Metabotropic glutamate receptor 4|mGluR<sub>4</sub>]]<sub>/</sub>[[Metabotropic glutamate receptor 6|<sub>6</sub>]]<sub>/</sub>[[Metabotropic glutamate receptor 7|<sub>7</sub>]]<sub>/</sub>[[Metabotropic glutamate receptor 8|<sub>8</sub>]]). It was the first ligand found to act as an agonist selective for this group of mGlu receptors,<ref>{{cite journal | vauthors = Thomsen C | title = The L-AP4 receptor | journal = General Pharmacology | volume = 29 | issue = 2 | pages = 151–8 | date = August 1997 | pmid = 9251893 | doi = 10.1016/S0306-3623(96)00417-X }}</ref> but does not show selectivity between the different mGluR Group III subtypes. It is widely used in the study of this receptor family and their various functions.<ref>{{cite journal | vauthors = Lopez S, Turle-Lorenzo N, Acher F, De Leonibus E, Mele A, Amalric M | title = Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease | journal = The Journal of Neuroscience | volume = 27 | issue = 25 | pages = 6701–11 | date = June 2007 | pmid = 17581957 | pmc = 6672706 | doi = 10.1523/JNEUROSCI.0299-07.2007 | url = https://hal.archives-ouvertes.fr/hal-00165896/document }}</ref><ref>{{cite journal | vauthors = Macinnes N, Duty S | title = Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo | journal = European Journal of Pharmacology | volume = 580 | issue = 1–2 | pages = 95–9 | date = February 2008 | pmid = 18035348 | doi = 10.1016/j.ejphar.2007.10.030 }}</ref><ref>{{cite journal | vauthors = Zhang HM, Chen SR, Pan HL | title = Effects of activation of group III metabotropic glutamate receptors on spinal synaptic transmission in a rat model of neuropathic pain | journal = Neuroscience | volume = 158 | issue = 2 | pages = 875–84 | date = January 2009 | pmid = 19017536 | pmc = 2649787 | doi = 10.1016/j.neuroscience.2008.10.042 }}</ref><ref>{{cite journal | vauthors = Maciejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, Lehner M, Bidziński A, Hamed A, Wisłowska-Stanek A, Płaźnik A | display-authors = 6 | title = The effects of group III mGluR ligands on pentylenetetrazol-induced kindling of seizures and hippocampal amino acids concentration | journal = Brain Research | volume = 1282 | pages = 20–7 | date = July 2009 | pmid = 19481536 | doi = 10.1016/j.brainres.2009.05.049 | s2cid = 20844494 }}</ref>


⚫
== References ==
{{Reflist|2}}


{{Metabotropic glutamate receptor modulators}}


⚫
[[Category:Alpha-Amino acids]]
{{pharm-stub}}
⚫
[[Category:Phosphonic acids]]
[[Category:MGlu4 receptor agonists]]
[[Category:MGlu6 receptor agonists]]
[[Category:MGlu7 receptor agonists]]
[[Category:MGlu8 receptor agonists]]


{{nervous-system-drug-stub}}
⚫
[[Category:Amino acids]]
⚫
[[Category:Organophosphonates]]

Latest revision as of 16:54, 17 September 2023

L-AP4
Clinical data
Other namesL-2-Amino-4-phosphonobutyric acid
Identifiers
  • (2S)-2-Amino-4-phosphonobutanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.164.384 Edit this at Wikidata
Chemical and physical data
FormulaC4H10NO5P
Molar mass183.100 g·mol−1
3D model (JSmol)
  • C(CP(=O)(O)O)[C@@H](C(=O)O)N
  • InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1 ☒N
  • Key:DDOQBQRIEWHWBT-VKHMYHEASA-N ☒N
 ☒NcheckY (what is this?)  (verify)

L-AP4 (L-2-amino-4-phosphonobutyric acid) is a drug used in scientific research, which acts as a group-selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8). It was the first ligand found to act as an agonist selective for this group of mGlu receptors,[1] but does not show selectivity between the different mGluR Group III subtypes. It is widely used in the study of this receptor family and their various functions.[2][3][4][5]

References

[edit]
  1. ^ Thomsen C (August 1997). "The L-AP4 receptor". General Pharmacology. 29 (2): 151–8. doi:10.1016/S0306-3623(96)00417-X. PMID 9251893.
  2. ^ Lopez S, Turle-Lorenzo N, Acher F, De Leonibus E, Mele A, Amalric M (June 2007). "Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease". The Journal of Neuroscience. 27 (25): 6701–11. doi:10.1523/JNEUROSCI.0299-07.2007. PMC 6672706. PMID 17581957.
  3. ^ Macinnes N, Duty S (February 2008). "Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo". European Journal of Pharmacology. 580 (1–2): 95–9. doi:10.1016/j.ejphar.2007.10.030. PMID 18035348.
  4. ^ Zhang HM, Chen SR, Pan HL (January 2009). "Effects of activation of group III metabotropic glutamate receptors on spinal synaptic transmission in a rat model of neuropathic pain". Neuroscience. 158 (2): 875–84. doi:10.1016/j.neuroscience.2008.10.042. PMC 2649787. PMID 19017536.
  5. ^ Maciejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, et al. (July 2009). "The effects of group III mGluR ligands on pentylenetetrazol-induced kindling of seizures and hippocampal amino acids concentration". Brain Research. 1282: 20–7. doi:10.1016/j.brainres.2009.05.049. PMID 19481536. S2CID 20844494.
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