5333. Lacosamide

Nomenclature

CAS number: 175481-36-4
(2R)-2-(Acetylamino)-3-methoxy-N-(phenylmethyl)propanamide; (R)-N-benzyl-2-acetamido-3-methoxypropionamide; erlosamide; harkoseride; ADD-234037; SPM-927.
C13H18N2O3; mol wt 250.29.
C 62.38%, H 7.25%, N 11.19%, O 19.18%.

Description and 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. Sthr 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).

Chemical structure

Properties

White solid, mp 143-144°. [α]D23 +16.0° (c = 1 in CH3OH).

Therapeutic Category

Analgesic; anticonvulsant.

Keywords

Anticonvulsant; Analgesic; Non-opioids