ravuconazole

CHEBI:143825 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14α demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4) — 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

triazole antifungalARO:3007499

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:18379
Label unavailable CHEBI:26878
Label unavailable CHEBI:35496
Label unavailable CHEBI:35727
Label unavailable CHEBI:38418
triazole antifungal ARO:3007499

Chemical structure

Computed structure properties
Molecular formula	C22H17F2N5OS
Charge	0
Average mass	437.475 Da
Monoisotopic mass	437.11219 Da
Source	ChEBI
InChIKey	OPAHEYNNJWPQPX-RCDICMHDSA-N

SMILES

C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F

InChI

InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1

Also called

ravuconazol (INN)— chebi
ravuconazolum (INN)— chebi
4-[2-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile (EXACT_SYNONYM)— chebi
BMS 207147 (EXACT_SYNONYM)— chebi
BMS-20714 (EXACT_SYNONYM)— chebi
ER 30346 (EXACT_SYNONYM)— chebi
ER-30346 (EXACT_SYNONYM)— chebi

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.

antileishmanial agent CHEBI:70868
antifungal drug 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:3009162`	ravuconazole	`antibioticmech:aro-ebc51e95f0`	2026-08-30
CHEBI	`CHEBI:143825`	ravuconazole	`antibioticmech:chebi-17acfad2b4`	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.

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Aspergillus flavus Cyp51A with mutations conferring resistance to ravuconazole	ARO:3009497	not organism-specific	—	ARO:3009497 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009162 (ravuconazole); database assertion, not a primary citation.)
Aspergillus fumigatus cyp51a with mutations conferring resistance to ravuconazole	ARO:3009204	not organism-specific	—	ARO:3009204 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009162 (ravuconazole); 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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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