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.
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
Equivalent identifiers for this same structure in other resources.
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
| 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 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 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
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.