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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

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

imidazole antibioticARO:3007500

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC22H17ClN2
Charge0
Average mass344.845 Da
Monoisotopic mass344.10803 Da
SourceChEBI
InChIKeyVNFPBHJOKIVQEB-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

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.

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.

Patents and articles

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

Activity roles

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

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

ANTIBIOTIC_TARGET_ALTERATION 4
ANTIBIOTIC_TARGET_ALTERATION
DeterminantARO IDOrganismGene familiesEvidence
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.)

Discussions

Open questions, knowledge gaps and curation todos attached to this compound.

CURATION_TODO OPEN

Reconcile the ATP1/ATP2 CARD assertions with exact source-row, experimental-background and endpoint evidence before assigning tested alleles or interpreting target alteration mechanistically.

Taylor et al. (2022) report ATP1/ATP2 changes in evolved multi-gene laboratory yeast backgrounds. Their tested ATP2 single mutants grew more slowly than the wild-type comparator in the reported growth analysis. Combination effects depend on background and condition; this is neither proof of a standalone ATP2 resistance effect nor evidence against every ATP2 allele. The exact FungAMR-row crosswalk to this independently identified study remains unresolved. Retain the CARD assertions as database provenance, not a newly verified direct ATP-synthase drug target.

Attached to: resistance_mechanisms#ARO:3009347, resistance_mechanisms#ARO:3009350

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

  7. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  8. CURATED_EVIDENCE_SCOPE_DISCUSSION 2026-10-13 · codex · LLM-assisted

    Added an evidence-backed ATP1/ATP2 scope discussion retaining negative and conditional laboratory growth findings. Preserved all four CARD assertions and SEEDED review status. UniProt entries remain reference-only; no experimental allele, genome or new resistance claim assigned.

Provenance

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

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