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	257.182 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 ;
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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

↑ "Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists.". Bioorganic & Medicinal Chemistry Letters 7 (9): 1195–1198. May 1997. doi:10.1016/S0960-894X(97)00177-7.
↑ "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. January 1999. doi:10.1021/jo981297a. PMID 11674092.
↑ "Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens". The Journal of Pharmacology and Experimental Therapeutics 300 (1): 162–71. January 2002. doi:10.1124/jpet.300.1.162. PMID 11752112.
↑ "The origin and neuronal function of in vivo nonsynaptic glutamate". The Journal of Neuroscience 22 (20): 9134–41. October 2002. doi:10.1523/JNEUROSCI.22-20-09134.2002. PMID 12388621.
↑ "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. August 2006. doi:10.1002/jnr.20897. PMID 16752416.

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[1] "Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists.". Bioorganic & Medicinal Chemistry Letters 7 (9): 1195–1198. May 1997. doi:10.1016/S0960-894X(97)00177-7.

[2] "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. January 1999. doi:10.1021/jo981297a. PMID 11674092.

[3] "Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens". The Journal of Pharmacology and Experimental Therapeutics 300 (1): 162–71. January 2002. doi:10.1124/jpet.300.1.162. PMID 11752112.

[4] "The origin and neuronal function of in vivo nonsynaptic glutamate". The Journal of Neuroscience 22 (20): 9134–41. October 2002. doi:10.1523/JNEUROSCI.22-20-09134.2002. PMID 12388621.

[5] "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. August 2006. doi:10.1002/jnr.20897. PMID 16752416.

Clinical data

ATC code	none
Identifiers
IUPAC name 1-Amino-5-phosphonoindan-1-carboxylic acid
ChemSpider	3881975^Y
ChEMBL	ChEMBL277961^Y
Chemical and physical data
Formula	C₁₀H₁₂NO₅P
Molar mass	257.182 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)^Y Key:ZNQZXIHSJUDIKL-UHFFFAOYSA-N^Y
(verify)