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.^[1] It is specifically used for multibacillary (MB) leprosy and erythema nodosum leprosum.^[2] Evidence is insufficient to support its use in other conditions^[1] though a retrospective study found it 95% effective in the treatment of Mycobacterium avium complex (MAC) when administered with a macrolide and ethambutol,^[3] as well as the drugs amikacin and clarithromycin.^[4] 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.^[5] It is taken orally.^[1]

Common side effects include abdominal pain, diarrhea, itchiness, dry skin, and change in skin color.^[1] It can also cause swelling of the lining of the gastrointestinal tract, increased blood sugar, and sensitivity to the sun.^[2] It is unclear if use during pregnancy is safe.^[1] Clofazimine is a phenazine dye and is believed to work by interfering with DNA.^[1]

Clofazimine was discovered in the 1950s at Trinity College, Dublin,^[6] and approved for medical use in the United States in 1986.^[1] It is on the World Health Organization's List of Essential Medicines.^[7] In the United States it is not available commercially but can be obtained from the US Department of Health and Human Services.^[1]

^ ^a ^b ^c ^d ^e ^f ^g ^h "Clofazimine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ ^a ^b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 132. hdl:10665/44053. ISBN 9789241547659.
^ Jarand J, Davis JP, Cowie RL, Field SK, Fisher DA (May 2016). "Long-term Follow-up of Mycobacterium avium Complex Lung Disease in Patients Treated With Regimens Including Clofazimine and/or Rifampin". Chest. 149 (5): 1285–1293. doi:10.1378/chest.15-0543. PMID 26513209.
^ "Clofazimine Prevents the Regrowth of Mycobacterium abscessus and Mycobacterium avium Type Strains Exposed to Amikacin and Clarithromycin".
^ "Clofazimine in the Treatment of Pulmonary Mycobacterium Avium Complex (MAC) | Clinical Research Trial Listing ( Mycobacterium avium Complex | MAC Infection (Mycobacterium Avium Complex) | Mycobacterium avium-intracellulare Infection ) ( NCT02968212 )". Archived from the original on 2022-09-13. Retrieved 2020-11-11.
^ Greenwood D (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 200. ISBN 9780199534845. By 1954 related molecules known as iminophenazines were being investigated... one of the first ones to be made, originally given the laboratory code B663 ... B663—subsequently called clofazimine
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[AHFS2016-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h "Clofazimine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[WHO2008-2] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 132. hdl:10665/44053. ISBN 9789241547659.

[3] Jarand J, Davis JP, Cowie RL, Field SK, Fisher DA (May 2016). "Long-term Follow-up of Mycobacterium avium Complex Lung Disease in Patients Treated With Regimens Including Clofazimine and/or Rifampin". Chest. 149 (5): 1285–1293. doi:10.1378/chest.15-0543. PMID 26513209.

[4] "Clofazimine Prevents the Regrowth of Mycobacterium abscessus and Mycobacterium avium Type Strains Exposed to Amikacin and Clarithromycin".

[5] "Clofazimine in the Treatment of Pulmonary Mycobacterium Avium Complex (MAC) | Clinical Research Trial Listing ( Mycobacterium avium Complex | MAC Infection (Mycobacterium Avium Complex) | Mycobacterium avium-intracellulare Infection ) ( NCT02968212 )". Archived from the original on 2022-09-13. Retrieved 2020-11-11.

[6] Greenwood D (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 200. ISBN 9780199534845. By 1954 related molecules known as iminophenazines were being investigated... one of the first ones to be made, originally given the laboratory code B663 ... B663—subsequently called clofazimine

[WHO21st-7] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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