Mr. Ibrahem/Clofazimine
Structural formula of clofazimine
Space-filling model of the clofazimine molecule
Clinical data
Trade namesLamprene
Other namesN,5-bis(4-chlorophenyl)-3-(1-methylethylimino)-5H-phenazin-2-amine
AHFS/Drugs.comMonograph
MedlinePlusa682128
Routes of
administration
By mouth
Drug classPhenazine dye[1]
Legal status
Legal status
Pharmacokinetic data
Elimination half-life70 days
Identifiers
  • N,5-bis(4-chlorophenyl)-3-(propan-2-ylimino)-3,5-dihydrophenazin-2-amine
Chemical and physical data
FormulaC27H22Cl2N4
Molar mass473.396 g·mol−1
3D model (JSmol)
Melting point210 to 212 °C (410 to 414 °F)
  • CC(C)/N=c/1\cc-2n(c3ccccc3nc2cc1Nc4ccc(cc4)Cl)c5ccc(cc5)Cl
  • 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 ☒N
  • Key:WDQPAMHFFCXSNU-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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.[3] Evidence is insufficient to support its use in other conditions.[1] It is taken by mouth.[1]

Common side effects include abdominal pain, diarrhea, itchiness, dry skin, and change in color of the skin.[1] May also cause swelling of the lining of the gastrointestinal tract, increased blood sugar, and sensitivity to the sun.[3] It is unclear if use during pregnancy is safe.[1] Clofazimine is a phenazine dye and believed to work by interfering with DNA.[1]

Clofazimine was discovered in the 1950s at Trinity College, Dublin,[4] and approved for medical use in the United States in 1986.[1] It is on the World Health Organization's List of Essential Medicines.[5] The wholesale cost in the developing world is about US$24 per month.[6] In the United States it is not available commercially but can be obtained from the US Department of Health and Human Services.[1]

References

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  1. ^ a b c d e f g h i j k "Clofazimine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  2. ^ Cite error: The named reference who was invoked but never defined (see the help page).
  3. ^ 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.
  4. ^ Greenwood, David (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 200. ISBN 9780199534845. Archived from the original on 2021-08-28. Retrieved 2019-07-31. 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
  5. ^ 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.
  6. ^ "Clofazimine". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 8 December 2016.