clofazimine

CHEBI:3749 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:39201 CHEBI:39201
CHEBI:83403 CHEBI:83403
ARO:3000003 ARO:3000003

Chemical structure

Computed structure properties
Molecular formula	C27H22Cl2N4
Charge	0
Average mass	473.407 Da
Monoisotopic mass	472.12215 Da
Source	ChEBI
InChIKey	WDQPAMHFFCXSNU-UHFFFAOYSA-N

SMILES

CC(C)N=c1cc2n(-c3ccc(Cl)cc3)c3ccccc3nc-2cc1Nc1ccc(Cl)cc1

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

Also called

clofazimina (INN)— chebi
clofaziminum (INN)— chebi
N,5-bis(4-chlorophenyl)-3-(propan-2-ylimino)-3,5-dihydrophenazin-2-amine (EXACT_SYNONYM)— chebi
(4-Chloro-phenyl)-[5-(4-chloro-phenyl)-3-isopropylimino-3,5-dihydro-phenazin-2-yl]-amine (EXACT_SYNONYM)— chebi
3-(p-chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine (EXACT_SYNONYM)— chebi
3-(p-chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin (EXACT_SYNONYM)— chebi
N,5-bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine (EXACT_SYNONYM)— chebi
Lampren (EXACT_SYNONYM)— aro
Lamprene (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004012
beilstein:8168151
cas:2030-63-9
drugbank:DB00845
kegg.compound:C06915
kegg.drug:D00278
lincs.smallmolecule:LSM-5669
patent:US2948726
chembl:CHEMBL1292
pubchem.compound:2794

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:35816 CHEBI:35816

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3004012`	clofazimine	`antibioticmech:aro-2f5364eabc`	2026-08-30
CHEBI	`CHEBI:3749`	clofazimine	`antibioticmech:chebi-fa5f5dc8e5`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

fluoroquinolone sensitive gyrA PROTEIN DIRECT_BINDING_TARGET

ARO:3000733

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO explicitly describes ligand binding to gyrase subunit A. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000733 (CARD/ARO asserts targeted_by_antibiotic ARO:3004012 (clofazimine); database assertion, not a primary citation.)

fluoroquinolone sensitive gyrB PROTEIN DIRECT_BINDING_TARGET

ARO:3003261

CARD/ARO database assertion; target organism, strain, and assay are not specified. GyrB is asserted as the fluoroquinolone-sensitive subunit. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003261 (CARD/ARO asserts targeted_by_antibiotic ARO:3004012 (clofazimine); database assertion, not a primary citation.)

Resistance mechanisms

3 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 3

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis Rv0678 with mutation conferring resistance to clofazimine	ARO:3007852	not organism-specific	—	ARO:3007852 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004012 (clofazimine); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv2535c with mutation conferring resistance to bedaquiline	ARO:3007692	not organism-specific	—	ARO:3007692 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004012 (clofazimine); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv2535c with mutation conferring resistance to clofazimine	ARO:3009335	not organism-specific	—	ARO:3009335 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004012 (clofazimine); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.