(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 64211-46-7
• PubChem SID: 46504752; 160963587
• PubChem CID: 5361463

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.312205
• LogD (pH = 7.4): 5.7768106
• Log P: 5.8387666
• Molar Refractivity: 105.947 cm^3
• Polarizability: 40.834076 Å^3
• Polar Surface Area: 39.41 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.28
• LOG S: -5.35
• Solubility (Water): 1.91e-03 g/l

DETAILS

DrugBank - DB00239

• 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

• Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. Pubmed
• 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