Back كلوفازيمين Arabic کلوفازیمین AZB Cloffasimin CY Clofazimin German Clofazimina Spanish کلوفازیمین FA Klofatsimiini Finnish Clofazimine French Կլոֆազիմին HY Klofazimin ID

Clofazimine

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
ATC code
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.347 Edit this at Wikidata
Chemical and physical data
FormulaC27H22Cl2N4
Molar mass473.40 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.[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]

  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.
  2. ^ 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.
  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. ^ Ferro BE, Meletiadis J, Wattenberg M, de Jong A, van Soolingen D, Mouton JW, et al. (February 2016). "Clofazimine Prevents the Regrowth of Mycobacterium abscessus and Mycobacterium avium Type Strains Exposed to Amikacin and Clarithromycin". Antimicrobial Agents and Chemotherapy. 60 (2): 1097–1105. doi:10.1128/aac.02615-15. PMC 4750661. PMID 26643335.
  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
  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.

Clofazimine

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