Clofazimine

Clofazimine
Clinical data
Trade names	Lamprene
Other names	N,5-bis(4-chlorophenyl)-3-(1-methylethylimino)-5H-phenazin-2-amine
AHFS/Drugs.com	Monograph
MedlinePlus	a682128
Routes of; administration	By mouth
ATC code	J04BA01 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Elimination half-life	70 days
Identifiers
	IUPAC name N,5-bis(4-chlorophenyl)-3-(propan-2-ylimino)-3,5-dihydrophenazin-2-amine;
CAS Number	2030-63-9 ;
PubChem CID	2794;
DrugBank	DB00845 ;
ChemSpider	21159573 ;
UNII	D959AE5USF;
KEGG	D00278 ;
ChEMBL	ChEMBL1292 ;
CompTox Dashboard (EPA)	DTXSID7022839 ;
ECHA InfoCard	100.016.347
Chemical and physical data
Formula	C27H22Cl2N4
Molar mass	473.40 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	210 to 212 °C (410 to 414 °F)
	SMILES CC(C)/N=c/1\cc-2n(c3ccccc3nc2cc1Nc4ccc(cc4)Cl)c5ccc(cc5)Cl;
	InChI InChI=1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3 ; Key:WDQPAMHFFCXSNU-UHFFFAOYSA-N ;
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Clofazimine, sold under the brand name Lamprene, is a medication used together with rifampicin and dapsone to treat leprosy. It is specifically used for multibacillary (MB) leprosy and erythema nodosum leprosum. Evidence is insufficient to support its use in other conditions though a retrospective study found it 95% effective in the treatment of Mycobacterium avium complex (MAC) when administered with a macrolide and ethambutol, as well as the drugs amikacin and clarithromycin. However, in the United States, clofazimine is considered an orphan drug, is unavailable in pharmacies, and its use in the treatment of MAC is overseen by the Food and Drug Administration. It is taken orally.

Common side effects include abdominal pain, diarrhea, itchiness, dry skin, and change in skin color. It can also cause swelling of the lining of the gastrointestinal tract, increased blood sugar, and sensitivity to the sun. It is unclear if use during pregnancy is safe. Clofazimine is a phenazine dye and is believed to work by interfering with DNA.

Clofazimine was discovered in the 1950s at Trinity College, Dublin, and approved for medical use in the United States in 1986. It is on the World Health Organization's List of Essential Medicines. In the United States it is not available commercially but can be obtained from the US Department of Health and Human Services.

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