clofazimine (CHEBI:3749)

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ChEBI Name	clofazimine

ChEBI ID	CHEBI:3749

Definition	3-Isopropylimino-3,5-dihydro-phenazine in which the hydrogen at position 5 is substituted substituted by a 4-chlorophenyl group, and that at position 2 is substituted by a (4-chlorophenyl)amino group. A dark red crystalline solid, clofazimine is an antimycobacterial and is one of the main drugs used for the treatment of multi-bacillary leprosy. However, it can cause red/brown discolouration of the skin, so other treatments are often preferred in light-skinned patients.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:355347

Supplier Information

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Formula

C27H22Cl2N4

Net Charge

Average Mass

473.39600

Monoisotopic Mass

472.12215

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

InChIKey

WDQPAMHFFCXSNU-UHFFFAOYSA-N

SMILES

CC(C)N=c1cc2n(-c3ccc(Cl)cc3)c3ccccc3nc2cc1Nc1ccc(Cl)cc1

Roles Classification
Biological Role(s):	leprostatic drug A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.

Application(s):	leprostatic drug A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions. non-steroidal anti-inflammatory drug An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. dye

ChEBI Ontology
Outgoing	clofazimine (CHEBI:3749) has role dye (CHEBI:37958) clofazimine (CHEBI:3749) has role leprostatic drug (CHEBI:35816) clofazimine (CHEBI:3749) has role non-steroidal anti-inflammatory drug (CHEBI:35475) clofazimine (CHEBI:3749) is a monochlorobenzenes (CHEBI:83403) clofazimine (CHEBI:3749) is a phenazines (CHEBI:39201)

IUPAC Name

N,5-bis(4-chlorophenyl)-3-(propan-2-ylimino)-3,5-dihydrophenazin-2-amine

Synonyms	Sources
(4-Chloro-phenyl)-[5-(4-chloro-phenyl)-3-isopropylimino-3,5-dihydro-phenazin-2-yl]-amine	ChEMBL
3-(p-chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine	ChemIDplus
3-(p-chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin	ChemIDplus
N,5-bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine	ChEMBL

Last Modified

22 February 2017