Title: Pregabalin
CAS Registry Number: 148553-50-8
CAS Name: (3S)-3-(Aminomethyl)-5-methylhexanoic acid
Additional Names: (S)-(+)-4-amino-3-(2-methylpropyl)butanoic acid; (S)-(+)-3-isobutyl-g-aminobutyric acid
Manufacturers' Codes: CI-1008; PD-144723
Trademarks: Lyrica (Pfizer)
Molecular Formula: C8H17NO2
Molecular Weight: 159.23
Percent Composition: C 60.34%, H 10.76%, N 8.80%, O 20.10%
Literature References: Structural analog of g-aminobutyric acid, q.v.; ligand at a2d subunit of voltage-gated calcium channels. Prepn of racemate: R. Andruszkiewicz, R. B. Silverman, Synthesis 1989, 953. Enantioselective synthesis: P. Yuen et al., Bioorg. Med. Chem. Lett. 4, 823 (1994). Manufacturing process: M. S. Hoekstra et al., Org. Process Res. Dev. 1, 26 (1997). HPLC determn in biological fluids: B. L. Windsor, L. L. Radulovic, J. Chromatogr. B 674, 143 (1995). Clinical trial in post-herpetic neuralgia: R. Sabatowski et al., Pain 109, 26 (2004). Overview of mechanism and pharmacology: S. M. Stahl, J. Clin. Psychiatry 65, 596, 1033 (2004). Review of pharmacology and clinical experience: B. A. Lauria-Horner, R. B. Pohl, Expert Opin. Invest. Drugs 12, 663-672 (2003); R. Huckle, Curr. Opin. Invest. Drugs 5, 82-89 (2004).
Properties: White crystalline solid, mp 186-188°. [a]D23 +10.52° (c = 1.06 in water).
Melting point: mp 186-188°
Optical Rotation: [a]D23 +10.52° (c = 1.06 in water)
Therap-Cat: Anticonvulsant; anxiolytic; analgesic in treatment of peripheral neuropathic pain.
Keywords: Anticonvulsant; Anxiolytic; Analgesic (Non-Narcotic). |