Basic information
- CAS
99592-39-9- Standard SMILES
Clc1ccc(C(Cn2ccnc2)OCc2csc3c(Cl)cccc23)c(Cl)c1.O=[N+]([O-])O- InChIKey
HAAITRDZHUANGT-UHFFFAOYSA-N- Molecular formula
- C20H16Cl3N3O4S
- Average molar mass
- 500.8 g/mol
- Monoisotopic mass
- 498.99271003
Overview
Sertaconazole Nitrate is the nitrate salt form of sertaconazole, a synthetic imidazole derivative with antifungal property. Sertaconazole nitrate inhibits fungal cytochrome P-450 sterol C-14 alpha-demethylation, resulting in the accumulation of fungal 14 alpha-methyl sterols and the inhibition of ergosterol synthesis, an essential component of the cell membrane of fungi. This leads to a disruption of cell membrane permeability and leakage of adenine triphosphate (ATP) and other constituents from fugal cells.
Names & identifiers
- Preferred name
- Sertaconazole Nitrate
- IUPAC
- 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid
- English name
- Sertaconazole nitrate
- Molecular formula
- C20H15Cl3N2OS.HNO3
- Molecular weight
- 500.78
Names & synonyms
Sertaconazole nitrate99592-39-9DermofixErtaczoZalainDermovitSertaconazole mononitrateFI 7056DTXSID20455291DV05410M5FI-7056DTXCID0025529
Show more names
SEROTONINGinedermofixSertaconazle NitrateNITRATE SERTACONAZOLE
1H-Imidazole, 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-, mononitrateRefChem:56606CHEBI:83687DermosepticFisdermExtensOnabetSertaconazole (nitrate)
Database identifiers
- CAS
99592-39-9- PubChem CID
- 200103
- DTXSID
DTXSID2045529- ChEMBL
CHEMBL1200725- UNII
- 1DV05410M5
- EC Number
- 893-241-3
Properties
Computed structural properties
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 513
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 158 · 158-160°
- storage temp.
- -20 °C · -20°C
- solubility
- 20 mg/mL, · DMSO: soluble20mg/mL, clear
- form
- powder
- pka
- 7.26 · pKb: 7.26(at 25℃)
- color
- white to beige
- InChI
- 1S/C20H15Cl3N2OS.HNO3/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;2-1(3)4/h1-8,11-12,19H,9-10H2;(H,2,3,4)
- InChIKey
- HAAITRDZHUANGT-UHFFFAOYSA-N
- SMILES
- [s]1c2c(c(c1)COC(C[n]4cncc4)c3c(cc(cc3)Cl)Cl)cccc2Cl.[N+](=O)([O-])O
- FDA UNII
- 1 DV05410M5 · 1DV05410M5
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 361 d · H361d
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Repr. 2
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
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Exposure RoutesBioavailability is negligible.
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.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361d
- Hazard Classifications
- Repr. 2
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
SERTACONAZOLE NITRATE
Azoles [CS]; Azole Antifungal [EPC]
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
UsesFor 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 nitrate is a new broad spectrum imidazole antifungal agent introduced in a topical formulation for the treatment of cutaneous infections. Its mechanism of action is the inhibition of ergosterol synthesis and interference with the permeability of fungus cell membranes. An oral formulation is currently under investigation for the treatment of bucco-pharyngeal fungal infections.
UsesAn imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.
UsesAntibacterial;ergosterol synthesis inhibitor
Suppliers100 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
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艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
河南赢创生物科技有限公司16650615803 · [email protected]
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Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
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銳迪國際科技有限公司18024082417 · [email protected]
南京诺利斯医药科技有限公司13901585132 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
ChemeGen 中国18818260767 · [email protected]
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BOC Sciences16314854226; +8616314854226 · [email protected]
湖北威德利化学试剂有限公司18327179646 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
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Target molecule Corp.857-239-0968 · [email protected]
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成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
Related reactions
1 records
Compound notes
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