CHEBI:83685 - arasertaconazole

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ChEBI Name arasertaconazole
ChEBI ID CHEBI:83685
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H15Cl3N2OS
Net Charge 0
Average Mass 437.77000
Monoisotopic Mass 435.99707
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
InChIKey JLGKQTAYUIMGRK-IBGZPJMESA-N
SMILES Clc1ccc([C@H](Cn2ccnc2)OCc2csc3c(Cl)cccc23)c(Cl)c1
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of EC 1.14.13.70 (sterol 14alpha-demethylase).
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via conazole antifungal drug )
(via imidazole antifungal drug )
ergosterol biosynthesis inhibitor
Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
(via conazole antifungal agent )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via conazole antifungal agent )
(via imidazole antifungal agent )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via conazole antifungal drug )
(via imidazole antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing arasertaconazole (CHEBI:83685) has role antibacterial drug (CHEBI:36047)
arasertaconazole (CHEBI:83685) has role antipruritic drug (CHEBI:59683)
arasertaconazole (CHEBI:83685) has role EC 1.14.13.70 (sterol 14α-demethylase) inhibitor (CHEBI:77884)
arasertaconazole (CHEBI:83685) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
arasertaconazole (CHEBI:83685) is a 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole (CHEBI:83682)
arasertaconazole (CHEBI:83685) is a conazole antifungal drug (CHEBI:87071)
arasertaconazole (CHEBI:83685) is a imidazole antifungal drug (CHEBI:87069)
arasertaconazole (CHEBI:83685) is conjugate base of arasertaconazole(1+) (CHEBI:83699)
arasertaconazole (CHEBI:83685) is enantiomer of (S)-sertaconazole (CHEBI:83684)
Incoming sertaconazole (CHEBI:82866) has part arasertaconazole (CHEBI:83685)
arasertaconazole(1+) (CHEBI:83699) is conjugate acid of arasertaconazole (CHEBI:83685)
(S)-sertaconazole (CHEBI:83684) is enantiomer of arasertaconazole (CHEBI:83685)
IUPAC Name
1-[(2R)-2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
INNs Sources
arasertaconazol WHO MedNet
arasertaconazole WHO MedNet
arasertaconazole ChemIDplus
arasertaconazolum WHO MedNet
Synonym Source
(R)-sertaconazole ChEBI
Manual Xrefs Databases
EP2436374 Patent
WO2012041966 Patent
View more database links
Registry Numbers Types Sources
11333066 Reaxys Registry Number Reaxys
583057-48-1 CAS Registry Number ChemIDplus
Last Modified
22 July 2015