AntibioticMech

clotrimazole

CHEBI:3764 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of imidazoles that is 1H-imidazole in which the hydrogen attached to a nitrogen is replaced by a monochlorotrityl group. — ChEBI

Classification

imidazole antibioticARO:3007500

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:24780 CHEBI:24780
• CHEBI:83403 CHEBI:83403
• CHEBI:87069 CHEBI:87069
• CHEBI:87071 CHEBI:87071
• ARO:3007500 ARO:3007500

Chemical structure

Computed structure properties

Molecular formula	C22H17ClN2
Charge	0
Average mass	344.845 Da
Monoisotopic mass	344.10803 Da
Source	ChEBI
InChIKey	VNFPBHJOKIVQEB-UHFFFAOYSA-N

SMILES

Clc1ccccc1C(c1ccccc1)(c1ccccc1)n1ccnc1

InChI

InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H

Also called

• 1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole (EXACT_SYNONYM)— chebi
• 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (EXACT_SYNONYM)— chebi
• 1-(o-Chloro-α,α-diphenylbenzyl)imidazole (EXACT_SYNONYM)— chebi
• 1-(o-Chlorotrityl)imidazole (EXACT_SYNONYM)— chebi
• 1-(α-(2-Chlorophenyl)benzhydryl)imidazole (EXACT_SYNONYM)— chebi
• Clotrimazole (EXACT_SYNONYM)— chebi
• Lotrimin (TN) (EXACT_SYNONYM)— chebi
• Mycelex (TN) (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3007516
• cas:23593-75-1
• drugbank:DB00257
• drugcentral:719
• hmdb:HMDB0001922
• kegg.compound:C06922
• kegg.drug:D00282
• lincs.smallmolecule:LSM-5341
• pdb-ccd:CL6
• reaxys:622318
• wikipedia.en:Clotrimazole
• chembl:CHEMBL104
• pubchem.compound:2812

Activity roles

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

• CHEBI:35718 CHEBI:35718
• CHEBI:86327 CHEBI:86327

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:3007516	clotrimazole	antibioticmech:aro-e4d7813500	2026-08-30
CHEBI	CHEBI:3764	clotrimazole	antibioticmech:chebi-3d81313bcc	2026-08-30

Mechanism summary

Mode of action

ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:75282 (ergosterol biosynthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Clinical status

APPROVED

Resistance mechanisms

4 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 4

ANTIBIOTIC_TARGET_ALTERATION

Determinant	ARO ID	Organism	Gene families	Evidence
Candida albicans Erg11 with mutations conferring resistance to clotrimazole	ARO:3009303	not organism-specific	—	ARO:3009303 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007516 (clotrimazole); database assertion, not a primary citation.)
Candida tropicalis Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to clotrimazole	ARO:3009225	not organism-specific	—	ARO:3009225 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007516 (clotrimazole); database assertion, not a primary citation.)
Saccharomyces cerevisiae ATP1 with mutations conferring resistance to clotrimazole	ARO:3009347	not organism-specific	—	ARO:3009347 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007516 (clotrimazole); database assertion, not a primary citation.)
Saccharomyces cerevisiae ATP2 with mutations conferring resistance to clotrimazole	ARO:3009350	not organism-specific	—	ARO:3009350 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007516 (clotrimazole); database assertion, not a primary citation.)

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 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. 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.