Structure via PubChem · Public domain (PubChem)
clofazimine
Sign in to saveAlso known as LAM320, Lamprene®, 3-(p-chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine
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, and its discovery greatly improved the overall efficiency of the treatment. 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 together with a macrolide and ethambutol, as well as the drugs amikacin and clarithromycin. However, in the United States,
Chemical data
- Formula
- C27H22Cl2N4
- Molecular weight
- 473.4 g/mol
- IUPAC name
- N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine
- SMILES
- CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
- InChIKey
- WDQPAMHFFCXSNU-UHFFFAOYSA-N
- XLogP
- 7.1
- Polar surface area
- 40 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,472 papers- Clofazimine: A journey of a drug.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023
- Clofazimine--a review.Indian journal of leprosy · 1991
- Impacts of clofazimine on the treatment outcomes of drug-resistant tuberculosis.Microbes and infection · 2023
- Clofazimine.Tuberculosis (Edinburgh, Scotland) · 2008
- Safety and Efficacy of Clofazimine as an Alternative for Rifampicin in Mycobacterium avium Complex Pulmonary Disease Treatment: Outcomes of a Randomized Trial.Chest · 2024
via PubMed
Wikidata facts
- Mass
- 472.122152
- Has use
- medication
Show 9 more facts
- subject has role
- bactericide
- chemical formula
- C₂₇H₂₂Cl₂N₄
- MCN code
- 2933.99.93
- isomeric SMILES
- CC(C)/N=C/1\C=C2N(C3=CC=CC=C3N=C2C=C1NC4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl
- World Health Organisation international non-proprietary name
- clofazimine
- canonical SMILES
- CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
- defined daily dose
- 0.1
- Commons category
- Clofazimine
- found in taxon
- Streptomyces hygroscopicus
Sources (6)
via Wikidata · CC0
~6 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Side effects
- Mechanism
- Metabolism
- History
- Society and culture
- Research
- References
- External links
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, and its discovery greatly improved the overall efficiency of the treatment. 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 together with a macrolide and ethambutol, as well as the drugs amikacin and clarithromycin. However, in the United States, clofazimine is currently 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.
Excerpted from Wikipedia’s “clofazimine” article, available under the CC BY-SA 4.0 licence.