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99592-32-2 molecular structure
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1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

ChemBase ID: 1024
Molecular Formular: C20H15Cl3N2OS
Molecular Mass: 437.7699
Monoisotopic Mass: 435.99706715
SMILES and InChIs

SMILES:
Clc1c(C(OCc2c3c(sc2)c(Cl)ccc3)Cn2ccnc2)ccc(Cl)c1
Canonical SMILES:
Clc1ccc(c(c1)Cl)C(Cn1ccnc1)OCc1csc2c1cccc2Cl
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
InChIKey:
JLGKQTAYUIMGRK-UHFFFAOYSA-N

Cite this record

CBID:1024 http://www.chembase.cn/molecule-1024.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
IUPAC Traditional name
sertaconazole
Brand Name
Ertaczo
Synonyms
Sertaconazol [Spanish]
Sertaconazolum [Latin]
Sertaconazole
CAS Number
99592-32-2
PubChem SID
160964487
46507290
PubChem CID
65863

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB01153 external link
PubChem 65863 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 5.6981435  LogD (pH = 7.4) 6.1626396 
Log P 6.2283483  Molar Refractivity 111.6029 cm3
Polarizability 44.26195 Å3 Polar Surface Area 27.05 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.74  LOG S -4.84 
Solubility (Water) 6.37e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Practically insoluble expand Show data source
Hydrophobicity(logP)
6.2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01153 external link
Item Information
Drug Groups approved
Description Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot. [Wikipedia]
Indication For the topical treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum.
Pharmacology Sertaconazole is an imidazole/triazole type antifungal agent. Sertaconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent loss of normal sterols correlates with the accumulation of 14 α-methyl sterols in fungi and may be partly responsible for the fungistatic activity of fluconazole. Mammalian cell demethylation is much less sensitive to fluconazole inhibition. Sertaconazole exhibits in vitro activity against Cryptococcus neoformans and Candida spp. Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to Cryptococcus neoformans and for systemic infections due to Candida albicans.
Affected Organisms
Yeast and other fungi
Absorption Bioavailability is negligible.
Protein Binding >99% to plasma
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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