APICA (drug)

APICA

Systematic (IUPAC) name
1-Amino-5-phosphonoindan-1-carboxylic acid
Identifiers
ATC code	None
ChemSpider	3881975
ChEMBL	CHEMBL277961
Chemical data
Formula	C10H12NO5P
Molar mass	257.179 g/mol
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

1. Ma D, Tian H, Sun H, Kozikowski AP, Pshenichkin S, Wroblewski JT. Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists. Bioorganic & Medicinal Chemistry Letters. 1997 May 6;7(9):1195-1198. doi:10.1016/S0960-894X(97)00177-7
2. Ma D, Tian H, Zou G. 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. Journal of Organic Chemistry. 1999 Jan 8;64(1):120-125. PMID 11674092
3. Xi ZX, Baker DA, Shen H, Carson DS, Kalivas PW. Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens. Journal of Pharmacology and Experimental Therapeutics. 2002 Jan;300(1):162-71. doi:10.1124/jpet.300.1.162 PMID 11752112
4. Baker DA, Xi ZX, Shen H, Swanson CJ, Kalivas PW. The origin and neuronal function of in vivo nonsynaptic glutamate. Journal of Neuroscience. 2002 Oct 15;22(20):9134-41. PMID 12388621
5. Zhou F, Yao HH, Wu JY, Yang YJ, Ding JH, Zhang J, Hu G. Activation of Group II/III metabotropic glutamate receptors attenuates LPS-induced astroglial neurotoxicity via promoting glutamate uptake. Journal of Neuroscience Research. 2006 Aug 1;84(2):268-77. PMID 16752416