APICA (drug)

APICA
Clinical data
ATC code	none;
Identifiers
	IUPAC name 1-Amino-5-phosphonoindan-1-carboxylic acid;
ChemSpider	3881975 ;
ChEMBL	ChEMBL277961 ;
Chemical and physical data
Formula	C10H12NO5P
Molar mass	257.179 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=P(O)(O)c(c2)ccc1c2CCC1(N)C(O)=O;
	InChI InChI=1S/C10H12NO5P/c11-10(9(12)13)4-3-6-5-7(17(14,15)16)1-2-8(6)10/h1-2,5H,3-4,11H2,(H,12,13)(H2,14,15,16) ; Key:ZNQZXIHSJUDIKL-UHFFFAOYSA-N ;
(verify)

1-Amino-5-phosphonoindan-1-carboxylic acid (APICA) is a drug that is used in neuroscience research. It is a selective antagonist for the group II metabotropic glutamate receptors (mGluR_2/3), and has been useful in the study of this receptor subfamily.[1][2][3][4][5]

References

Ma D, Tian H, Sun H, Kozikowski AP, Pshenichkin S, Wroblewski JT (May 1997). "Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists". Bioorganic & Medicinal Chemistry Letters. 7 (9): 1195–1198. doi:10.1016/S0960-894X(97)00177-7.
Ma D, Tian H, Zou G (January 1999). "Asymmetric Strecker-Type Reaction of alpha-Aryl Ketones. Synthesis of (S)-alphaM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors". The Journal of Organic Chemistry. 64 (1): 120–125. doi:10.1021/jo981297a. PMID 11674092.
Xi ZX, Baker DA, Shen H, Carson DS, Kalivas PW (January 2002). "Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens". The Journal of Pharmacology and Experimental Therapeutics. 300 (1): 162–71. doi:10.1124/jpet.300.1.162. PMID 11752112.
Baker DA, Xi ZX, Shen H, Swanson CJ, Kalivas PW (October 2002). "The origin and neuronal function of in vivo nonsynaptic glutamate". The Journal of Neuroscience. 22 (20): 9134–41. doi:10.1523/JNEUROSCI.22-20-09134.2002. PMC 6757683. PMID 12388621.
Zhou F, Yao HH, Wu JY, Yang YJ, Ding JH, Zhang J, Hu G (August 2006). "Activation of Group II/III metabotropic glutamate receptors attenuates LPS-induced astroglial neurotoxicity via promoting glutamate uptake". Journal of Neuroscience Research. 84 (2): 268–77. doi:10.1002/jnr.20897. PMID 16752416.

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[1] Ma D, Tian H, Sun H, Kozikowski AP, Pshenichkin S, Wroblewski JT (May 1997). "Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists". Bioorganic & Medicinal Chemistry Letters. 7 (9): 1195–1198. doi:10.1016/S0960-894X(97)00177-7.

[2] Ma D, Tian H, Zou G (January 1999). "Asymmetric Strecker-Type Reaction of alpha-Aryl Ketones. Synthesis of (S)-alphaM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors". The Journal of Organic Chemistry. 64 (1): 120–125. doi:10.1021/jo981297a. PMID 11674092.

[3] Xi ZX, Baker DA, Shen H, Carson DS, Kalivas PW (January 2002). "Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens". The Journal of Pharmacology and Experimental Therapeutics. 300 (1): 162–71. doi:10.1124/jpet.300.1.162. PMID 11752112.

[4] Baker DA, Xi ZX, Shen H, Swanson CJ, Kalivas PW (October 2002). "The origin and neuronal function of in vivo nonsynaptic glutamate". The Journal of Neuroscience. 22 (20): 9134–41. doi:10.1523/JNEUROSCI.22-20-09134.2002. PMC 6757683. PMID 12388621.

[5] Zhou F, Yao HH, Wu JY, Yang YJ, Ding JH, Zhang J, Hu G (August 2006). "Activation of Group II/III metabotropic glutamate receptors attenuates LPS-induced astroglial neurotoxicity via promoting glutamate uptake". Journal of Neuroscience Research. 84 (2): 268–77. doi:10.1002/jnr.20897. PMID 16752416.