Clofazimine

Generic and additional names: 3-(p-chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine; 2-(4-chloroanilino)-3-isopropylimino-5-(4-chlorophenyl)-3,5-dihydrophenazine; 2-p-chloroanilino-5-p-chlorophenyl-3,5-dihydro-3-isopropyliminophenazineCAS name: N,5-bis(4-chlorophenyl)-3-(1-methylethylimino)-5H-phenazin-2-amineCAS registry #: 2030-63-9Molecular formula: C27H22Cl2N4Molecular weight: 473.40Intellectual property rights: Generic. Clofazimine was first synthesized in 1954 as an anti-tuberculosis lichen-derived compound. The drug was thought to be ineffective against tuberculosis but in 1959 Chang demonstrated its effectiveness against leprosy. After clinical trials the product was launched in 1969 as Lamprene. Marketed by Novartis as Lamprene.Brand names: Lampren(e) (Novartis)Derivatives: Riminophenazine analogs B4154 and B 4157.1Solubility: Soluble in dilute acetic acid, DMF. Soluble in 15 parts of chloroform, 700 parts of ethanol, 1000 parts of ether. Practically insoluble in water [Merck Index].Polarity: Log P 7.132 [DrugBank]Acidity/basicity: pKa 8.51 [DrugBank]Melting point: 210–212ºC [DrugBank]Formulation and optimal human dosage: Lamprene, 50 mg clofazimine. Daily dose 1–2 tablets (50–100 mg).2 Clofazimine is a substituted iminophenazine bright-red dye.Figure optionsDownload full-size imageDownload high-quality image (22 K)Download as PowerPoint slide