Sertaconazole

HCID 65863

Basic information

CAS
99592-32-2
Standard SMILES
Clc1ccc(C(Cn2ccnc2)OCc2csc3c(Cl)cccc23)c(Cl)c1
InChIKey
JLGKQTAYUIMGRK-UHFFFAOYSA-N
Molecular formula
C20H15Cl3N2OS
Average molar mass
437.8 g/mol
Monoisotopic mass
435.99706714

Overview

1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1. It is a dichlorobenzene, a member of imidazoles, an ether and a member of 1-benzothiophenes.

Names & identifiers

Preferred name
Sertaconazole
IUPAC
1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
English name
Sertaconazole
Molecular formula
C20H15Cl3N2OS
Molecular weight
437.77

Names & synonyms

Sertaconazole99592-32-2SertaconazolSertaconazolumFI-7045Demofix72W71I16EG1-(2-((7-Chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole7-Chloro-3-(1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy-methyl)benzo(b)thiopheneDTXSID0048551Ginedermofix
Show more names
Sertaconazole nitrateeno(RS)-1-(2-((7-chloro-1-benzothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl) -1H-imidazoleZalainFI-7056DermofixEnolase γ
1H-Imidazole, 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-7-Chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy-methyl]benzo[b]thiophene1-(2-((7-chloro-1-benzothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole1H-Imidazole, 1-[2-[(7-chlorobenzo[b]thien-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-RefChem:56490DTXCID6028107CHEBI:82866D01AC14

Database identifiers

CAS
99592-32-2
PubChem CID
65863
DTXSID
DTXSID0048551
ChEMBL
CHEMBL1201196
ChEBI
CHEBI:83682
UNII
72W71I16EG
EC Number
841-355-9
Nikkaji
J369.930G

Properties

Computed structural properties

XLogP
6.3
Topological polar surface area
55.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
27

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP6.2
Solubility · 2 items

Practically insoluble

6.37e-03 g/L

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physicochemical properties

Melting point
146 · 146-147°
Boiling point
614.1 · 614.1±55.0 °C(Predicted)
Density
1.43 · 1.43±0.1 g/cm3(Predicted)
storage temp.
Refrigerator
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Exposure RoutesBioavailability is negligible.
Toxicity Summary · 1 item

Sertaconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H319-H335-H315
Precautionary statements
P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Pharmacology

ATC Code · 4 items

D - Dermatologicals

G - Genito urinary system and sex hormones

QD - Dermatologicals

QG - Genito urinary system and sex hormones

Protein Binding>99% to plasma
Pharmacodynamics · 1 item

Sertaconazole is an imidazole/triazole type antifungal agent. Sertaconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 &alpha;-demethylation via the inhibition of the enzyme cytochrome P450 14&alpha;-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 &alpha;-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 <i>in vitro</i> activity against <i>Cryptococcus neoformans</i> and <i>Candida spp.</i> Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to <i>Cryptococcus neoformans</i> and for systemic infections due to Candida albicans.

Mechanism of Action · 1 item

Sertaconazole interacts with 14-&alpha; demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

FDA Pharmacological Classification · 5 items

72W71I16EG

SERTACONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Sertaconazole is an Azole Antifungal.

MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Uses & manufacturing

Uses · 2 items

Use (kg; approx.) in Germany (2009): >100

For the topical treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by <i>Trichophyton rubrum</i>, <i>Trichophyton mentagrophytes</i>, and <i>Epidermophyton floccosum</i>.

Applications · 2 items

DescriptionSertaconazole has been developed and launched for the treatment of dermatological fungal infections by Ferrer Internacional S. A. Mylan received FDA approval for sertaconazole nitrate cream for the treatment of athlete's foot (tinea pedis) at the end of 2003.

UsesAn imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.

Suppliers64 total

北京华美互利生物化工010-56205725 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1. It is a dichlorobenzene, an ether, a member of imidazoles and a member of 1-benzothiophenes.

Related reactions

4 records

Compound notes

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