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C8895

Sigma-Aldrich

Clofazimine

≥98% (TLC), powder, antileprosy drug

Synonym(s):

N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-(isopropylimino)phenazin-2-amine

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About This Item

Empirical Formula (Hill Notation):
C27H22Cl2N4
CAS Number:
2030-63-9
Molecular Weight:
473.40
EC Number:
217-980-2
MDL number:
MFCD00056793
UNSPSC Code:
12352200
PubChem Substance ID:
24893114
NACRES:
NA.77

product name

Clofazimine,

form

powder

antibiotic activity spectrum

mycobacteria

Mode of action

protein synthesis | interferes

originator

Novartis

SMILES string

CC(C)\N=C1/C=C2N(c3ccc(Cl)cc3)c4ccccc4N=C2C=C1Nc5ccc(Cl)cc5

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/b30-24+

InChI key

WDQPAMHFFCXSNU-BGABXYSRSA-N

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General description

Clofazimine is a riminophenazine, which is used as an antileprosy drug. It is used to treat multidrug-resistant tuberculosis. Clofazimine prevents neutrophil motility and lymphocyte transformation. It has anti-inflammatory effect, which is used to treat discoid lupus erythematosus. Clofazimine has immunosuppressive property.

Application

Clofazimine has been used:
  • for antimicrobial preparation
  • to study its accumulation on macrophages to form crystal-like drug inclusions (CLDIs)
  • to model drug-induced hepatic granulomatous inflammation
  • to study the in vivo cargo storage capacity of macrophages

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mode of action of clofazimine and combination therapy with benzothiazinones against Mycobacterium tuberculosis
Lechartier B and Cole ST
Antimicrobial Agents and Chemotherapy, 59(8), 4457-4463 (2015)
Macrophage-mediated clofazimine sequestration is accompanied by a shift in host energy metabolism
Trexel J, et al.
Journal of Pharmaceutical Sciences, 106(4), 1162-1174 (2017)
Sarah Schmidt Grant et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(30), 12147-12152 (2012-07-11)
During Mycobacterium tuberculosis infection, a population of bacteria likely becomes refractory to antibiotic killing in the absence of genotypic resistance, making treatment challenging. We describe an in vitro model capable of yielding a phenotypically antibiotic-tolerant subpopulation of cells, often called
The Antimicrobial Drugs (2000)
In vitro approaches for generation of Mycobacterium tuberculosis mutants resistant to bedaquiline, clofazimine or linezolid and identification of associated genetic variants
Ismail N, et al.
Journal of Microbiological Methods, 153(8), 1-9 (2018)
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