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64211-46-7 molecular structure
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(E)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine

ChemBase ID: 124
Molecular Formular: C18H13Cl4N3O
Molecular Mass: 429.12732
Monoisotopic Mass: 426.98127277
SMILES and InChIs

SMILES:
Clc1c(/C(=N\OCc2c(Cl)cc(Cl)cc2)/Cn2ccnc2)ccc(Cl)c1
Canonical SMILES:
Clc1ccc(c(c1)Cl)CO/N=C(\c1ccc(cc1Cl)Cl)/Cn1cncc1
InChI:
InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18-
InChIKey:
QRJJEGAJXVEBNE-MOHJPFBDSA-N

Cite this record

CBID:124 http://www.chembase.cn/molecule-124.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(E)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine
IUPAC Traditional name
oxiconazole
Brand Name
Oxistat
Synonyms
Oxiconazole Nitrate
Oxiconazol [INN-Spanish]
Oxiconazolum [INN-Latin]
Oxiconazole
CAS Number
64211-46-7
PubChem SID
46504752
160963587
PubChem CID
5361463

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 5.312205  LogD (pH = 7.4) 5.7768106 
Log P 5.8387666  Molar Refractivity 105.947 cm3
Polarizability 40.834076 Å3 Polar Surface Area 39.41 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.28  LOG S -5.35 
Solubility (Water) 1.91e-03 g/l 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00239 external link
Item Information
Drug Groups approved
Description Oxiconazole nitrate (U.S.: Oxistat, Canada: Oxizole) is an antifungal medication typically administered in a cream or lotion to treat skin infections such as athlete's foot, jock itch and ringworm. [Wikipedia]
Indication For treatment of dermal fungal infection.
Pharmacology Oxiconazole is a broad-spectrum imidazole derivative whose antifungal activity is derived primarily from the inhibition of ergosterol biosynthesis, which is critical for cellular membrane integrity. It has fungicidal or fungistatic activity in vitro against a number of pathogenic fungi including the following dermatophytes, and yeasts: T. rubrum, T. mentagrophytes, T. tonsurans, T. violaceum, E. floccosum, M. canis, M. audouini, M. gypseum, C. albicans, and M. furfur.
Toxicity Side effects incliude pruritus, burning, irritation, erythema, stinging and allergic contact dermatitis and folliculitis, fissuring, maceration rash and nodules.
Affected Organisms
Fungi
Absorption Systemic absorption of oxiconazole is low.
References
Matsui H, Sakanashi Y, Oyama TM, Oyama Y, Yokota S, Ishida S, Okano Y, Oyama TB, Nishimura Y: Imidazole antifungals, but not triazole antifungals, increase membrane Zn2+ permeability in rat thymocytes Possible contribution to their cytotoxicity. Toxicology. 2008 Jun 27;248(2-3):142-50. Epub 2008 Apr 7. [Pubmed]
Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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  • • Matsui H, Sakanashi Y, Oyama TM, Oyama Y, Yokota S, Ishida S, Okano Y, Oyama TB, Nishimura Y: Imidazole antifungals, but not triazole antifungals, increase membrane Zn2+ permeability in rat thymocytes Possible contribution to their cytotoxicity. Toxicology. 2008 Jun 27;248(2-3):142-50. Epub 2008 Apr 7. Pubmed
  • • Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. Pubmed
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PATENTS

PATENTS

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INTERNET

INTERNET

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