Compound ID | 1420

Update compound information

Clofazimine

Synonym(s): Lamprene  |  B663  |  B 663  |  B-663

Class: Small molecule antibacterial agent

Agent Type: Semisynthetic; Synthetic; Small molecule;
Spectrum of activity: Antimycobacterial
Mechanism of action: Targets the redox cycling in Mycobacterium and potentially membrane disruption
Target Pathogen: Active against Mycobacterium avium and Mycobacterium leprae
Description: A riminophenazine
Institute where first reported: Novartis, Switzerland
Year first mentioned: 1986
Highest development stage: Approved by FDA in 1986
Development status: Approved
Reason dropped: Production discontinued by Novartis in US
Chemical structure(s):
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Molecular weight: 473.4
Iso. SMILES: CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
InChI Key: WDQPAMHFFCXSNU-UHFFFAOYSA-N
Can. SMILES: CC(C)N=C1C=C2C(=NC3=C(C=CC=C3)N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/2794
Guide to Pharmacology: clofazimine
Citations:
  • https://aac.asm.org/content/64/5/e02349-19
  • https://doi.org/10.1016/j.biopha.2023.115539
  • https://doi.org/10.1093/jac/dkw426
  • https://www.jaad.org/article/0190-9622(95)90134-5/pdf

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