5353. Lamotrigine

Nomenclature

CAS number: 84057-84-1
6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine; LTG; BW-430C; Lamictal (GSK).
C9H7Cl2N5; mol wt 256.09.
C 42.21%, H 2.76%, Cl 27.69%, N 27.35%.

Description and references

Prepn: M. G. Baxter et al., EP 21121 (1981 to Wellcome Foundation); D. A. Sawyer et al., US 4602017 (1986). HPLC determn in plasma: C.-L. Cheng et al., J. Chromatogr. B 817, 199 (2005). Anticonvulsant activity: A. A. Miller et al., Epilepsia 27, 483 (1986). Mechanism of action studies: M. J. Leach et al., ibid. 490; X. Xie, R. M. Hagan, Neuropsychobiology 38, 119 (1998). Series of articles on clinical pharmacology, antiepileptic efficacy and safety: Epilepsia 32, Suppl. 2, S1-S21 (1991). Clinical trial in bipolar depression: J. R. Calabrese et al., J. Clin. Psychiatry 60, 79 (1999). Review of clinical experience in epilepsy: H. Choi, M. J. Morrell, Expert Opin. Pharmacother. 4, 243-251 (2003); in bipolar disorder: Z. Bhagwagar, G. M. Goodwin, Expert Opin. Pharmacother. 6, 1401-1408 (2005).

Chemical structure

Properties

White to pale cream-colored powder. Crystals from isopropanol, mp 216-218° (uncorr). pKa 5.7. Soly at 25° (mg/ml): water 0.17; 0.1M HCl 4.1. LD50 in mice, rats (mg/kg): 250, >640 orally (Sawyer).

Therapeutic Category

Anticonvulsant. In treatment of bipolar depression.

Keywords

Anticonvulsant