Imagabalin

Imagabalin (INN, USAN; PD-0332334) was an investigational drug that acts as a ligand for the α₂δ subunit of the voltage-dependent calcium channel,^[1] with some selectivity for the α₂δ₁ subunit over α₂δ₂.^[2] It was under development by Pfizer as a pharmaceutical medication due to its hypothesized anxiolytic, analgesic, hypnotic, and anticonvulsant-like activity. It reached phase-III clinical trials for treatment of generalized anxiety disorder; however, the trials were terminated by the manufacturer.^[3][4][5][6] The drug is no longer under development.

Imagabalin

Clinical data
Other names	PD-0332334; PD-332,334
ATC code	None
Identifiers
IUPAC name (3S,5R)-3-amino-5-methyloctanoic acid
CAS Number	610300-07-7 610300-00-0 (hydrochloride)
PubChem CID	10236037
ChemSpider	8411525
UNII	NDG6931B7H
KEGG	D09627
CompTox Dashboard (EPA)	DTXSID00976534
Chemical and physical data
Formula	C9H19NO2
Molar mass	173.256 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(O)C[C@@H](N)C[C@@H](CCC)C
InChI InChI=1S/C9H19NO2/c1-3-4-7(2)5-8(10)6-9(11)12/h7-8H,3-6,10H2,1-2H3,(H,11,12)/t7-,8+/m1/s1 Key:JXEHXYFSIOYTAH-SFYZADRCSA-N

Synthesis

Protein engineering has been used to modify the Vibrio fluvialis aminotransferase to catalyze the asymmetric transamination of a synthetic intermediate.^[7]

See also

• Atagabalin
• PD-217,014
• Gabapentinoids