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

Classification

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:39201
• Label unavailable CHEBI:83403
• antibiotic without defined classification ARO:3000003

Chemical structure

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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

• clofazimineARO:3004012
• beilstein:8168151
• cas:2030-63-9
• kegg.compound:C06915
• lincs.smallmolecule:LSM-5669
• chembl:CHEMBL1292
• pubchem.compound:2794

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

• drugbank:DB00845
• kegg.drug:D00278

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

• patent:US2948726

Activity roles

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

• leprostatic drug 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.

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.)

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

242 observations · Browse all observations · Complete record (JSON.gz)

Observations 1–20 of 242

Resistance mechanisms

3 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-09-26 · seed_from_sources

   Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

7. RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources

   Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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