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
Show more names
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
- Formal charge
- 0
- Complexity
- 488
Experimental & physicochemical properties
Solubility
Practically insoluble
6.37e-03 g/L
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
- pka
- 6.68 · 6.68±0.12(Predicted)
- color
- White to Pale Yellow
- 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
- SMILES
- C1N(CC(OCC2=CSC3=C(Cl)C=CC=C32)C2=CC=C(Cl)C=C2Cl)C=CN=1
- CAS DataBase Reference
- 99592 · 99592-32-2(CAS DataBase Reference)
- FDA UNII
- 72 W71I16EG · 72W71I16EG
- ATC code
- 1 AC14,G01AF19 · D01AC14,G01AF19
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319-H335-H315
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Toxicity Summary
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.
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
D - Dermatologicals
G - Genito urinary system and sex hormones
QD - Dermatologicals
QG - Genito urinary system and sex hormones
Pharmacodynamics
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 <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
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.
FDA Pharmacological Classification
72W71I16EG
SERTACONAZOLE
Established Pharmacologic Class [EPC] - Azole Antifungal
Chemical Structure [CS] - Azoles
Sertaconazole is an Azole Antifungal.
Uses & manufacturing
Uses
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
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.
Upstream & downstream products
Upstream raw materials
Suppliers64 total
Additional notes
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
Compound notes
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