arasertaconazole

CHEBI:83685 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole that is the active R-enantiomer of sertaconazole and is used (as its nitrate salt) for treatment of vulvovaginal candidiasis. The racemate itself is also used as a broad-spectrum antifungal drug. — 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:83682 CHEBI:83682
CHEBI:87069 CHEBI:87069
CHEBI:87071 CHEBI:87071

Chemical structure

Computed structure properties
Molecular formula	C20H15Cl3N2OS
Charge	0
Average mass	437.779 Da
Monoisotopic mass	435.99707 Da
Source	ChEBI
InChIKey	JLGKQTAYUIMGRK-IBGZPJMESA-N

SMILES

Clc1ccc([C@H](Cn2ccnc2)OCc2csc3c(Cl)cccc23)c(Cl)c1

InChI

InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2/t19-/m0/s1

Also called

arasertaconazol (INN)— chebi
arasertaconazolum (INN)— chebi
1-[(2R)-2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole (EXACT_SYNONYM)— chebi
(R)-sertaconazole (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:583057-48-1
patent:EP2436374
patent:WO2012041966
reaxys:11333066

Activity roles

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

CHEBI:35718 CHEBI:35718
CHEBI:36047 CHEBI:36047
CHEBI:77884 CHEBI:77884
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
CHEBI	`CHEBI:83685`	arasertaconazole	`antibioticmech:chebi-226ba52641`	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, but this mechanism belongs to an anti-fungal activity while the record is filed as ANTIBACTERIAL. Either the compound has both activities, or the filing is wrong — the priority table has put azole antifungals under ANTIBACTERIAL before now. A curator should decide which. 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.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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 2026-08-30 · 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.