CHEBI:3749 - clofazimine

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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 0
Average Mass 473.39600
Monoisotopic Mass 472.122
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

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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
INNs Sources
clofazimina ChemIDplus
clofazimine ChemIDplus
clofaziminum ChemIDplus
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
Manual Xrefs Databases
C06915 KEGG COMPOUND
D00278 KEGG DRUG
DB00845 DrugBank
LSM-5669 LINCS
US2948726 Patent
View more database links
Registry Numbers Types Sources
2030-63-9 CAS Registry Number KEGG COMPOUND
2030-63-9 CAS Registry Number ChemIDplus
8168151 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17210775 PubMed citation ChEMBL
3279207 PubMed citation ChEMBL
Last Modified
22 February 2017