Lacosamide
Title: Lacosamide
CAS Registry Number: 175481-36-4
CAS Name: (2R)-2-(Acetylamino)-3-methoxy-N-(phenylmethyl)propanamide
Additional Names: (R)-N-benzyl-2-acetamido-3-methoxypropionamide; erlosamide; harkoseride
Manufacturers' Codes: ADD-234037; SPM-927
Molecular Formula: C13H18N2O3
Molecular Weight: 250.29
Percent Composition: C 62.38%, H 7.25%, N 11.19%, O 19.18%
Literature References: Functionalized amino acid with demonstrated anticonvulsant and analgesic activity. Prepn: D. Choi et al., J. Med. Chem. 39, 1907 (1996); H. Kohn, WO 9733861; idem, US 5773475 (1997, 1998 both to Research Corp. Technol.). Improved prepn and anticonvulsant activity: S. V. Andurkar et al., Tetrahedron: Asymmetry 9, 3841 (1998). Mode of action study: G. Lees et al., Neuropharmacology 50, 98 (2006). Evaluation in animal models of seizure: G. E. Duncan, H. Kohn, Epilepsy Res. 67, 81 (2005); of inflammatory pain: T. Stöhr et al., Eur. J. Pain 10, 241 (2006). Clinical evaluation in neuropathic pain: G. McCleane et al., Neurosci. Lett. 352, 117 (2003). Review of clinical development: C. A. Hovinga, IDrugs 6, 479-485 (2003).
Properties: White solid, mp 143-144°. [a]D23 +16.0° (c = 1 in CH3OH).
Melting point: mp 143-144°
Optical Rotation: [a]D23 +16.0° (c = 1 in CH3OH)
Therap-Cat: Analgesic; anticonvulsant.
Keywords: Analgesic (Non-Narcotic); Anticonvulsant.

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