isavuconazole
CHEBI:85979
·resolve ·ANTIFUNGAL
·EXACT
SEEDED
A 1,3-thiazole that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,5-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively. It is an antifungal drug used for the treatment of invasive aspergillosis and invasive mucormycosis. — 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 | DDFOUSQFMYRUQK-RCDICMHDSA-N |
|---|
SMILES
C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1cc(F)ccc1F
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)18-8-17(23)6-7-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
Also called
- isavuconazol (INN)— chebi
- isavuconazolum (INN)— chebi
- 4-{2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}benzonitrile (EXACT_SYNONYM)— chebi
- BAL 4815 (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:3007514 |
isavuconazole |
antibioticmech:aro-fc6eff5f3e |
2026-08-30 |
| CHEBI |
CHEBI:85979 |
isavuconazole |
antibioticmech:chebi-2b1b28d2c3 |
2026-08-30 |
Mechanism summary
- Mode of action
- ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:75282 (ergosterol biosynthesis inhibitor), CHEBI:77884 (EC 1.14.13.70 (sterol 14α-demethylase) 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
10 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 10
ANTIBIOTIC_TARGET_ALTERATION
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|
| Aspergillus flavus Cyp51C with mutations conferring resistance to isavuconazole |
ARO:3009490 |
not organism-specific |
— |
- ARO:3009490 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Aspergillus fumigatus Cyp51B with mutations conferring resistance to isavuconazole |
ARO:3009482 |
not organism-specific |
— |
- ARO:3009482 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Aspergillus fumigatus Cyp51a with mutations conferring resistance to isavuconazole |
ARO:3009499 |
not organism-specific |
— |
- ARO:3009499 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Aspergillus fumigatus Hmg1 with mutations conferring resistance to isavuconazole |
ARO:3009237 |
not organism-specific |
— |
- ARO:3009237 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Aspergillus fumigatus Hmg2 with mutations conferring resistance to isavuconazole |
ARO:3009367 |
not organism-specific |
— |
- ARO:3009367 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Aspergillus spp. Hmg1 with mutations conferring resistance to triazoles antibiotics |
ARO:3007670 |
not organism-specific |
— |
- ARO:3007670 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Candida albicans Erg11 with mutations conferring resistance to isavuconazole |
ARO:3009198 |
not organism-specific |
— |
- ARO:3009198 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Candida parapsilosis Erg3 C-5 sterol desaturase with mutations conferring resistance to isavuconazole |
ARO:3009627 |
not organism-specific |
— |
- ARO:3009627 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Nakaseomyces glabratus FKS2 beta-1,3-glucan synthase with mutations associated with resistance to isavuconazole |
ARO:3009617 |
not organism-specific |
— |
- ARO:3009617 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); database assertion, not a primary citation.)
|
| Nakaseomyces glabratus FSK1 beta-1,3-glucan synthase with mutations associated with resistance to isavuconazole |
ARO:3009612 |
not organism-specific |
— |
- ARO:3009612 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007514 (isavuconazole); 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.