WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 413203
CAS#: 74512-12-2 (free base)
Description: Omoconazole is an azole antifungal drug. Omonocazole is not available in the United States and Canada. In other countries, it is used to treat cutaneous candidiasis, dermatophytosis, pityriasis versicolor.
MedKoo Cat#: 413203
Name: Omoconazole
CAS#: 74512-12-2 (free base)
Chemical Formula: C20H17Cl3N2O2
Exact Mass: 422.0356
Molecular Weight: 423.72
Elemental Analysis: C, 56.69; H, 4.04; Cl, 25.10; N, 6.61; O, 7.55
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 74512-12-2 (free base) 83621-06-1 (nitrate)
Synonym: Omoconazole; CM8282; CM-8282; CM 8282
IUPAC/Chemical Name: (Z)-1-(2,4-Dichloro-beta-(2-(p-chlorophenoxy)ethoxy)-alpha-methylstyryl)imidazole
InChi Key: ZAATZLURMSCKQV-ZHZULCJRSA-N
InChi Code: InChI=1S/C20H17Cl3N2O2/c1-14(18-7-4-16(22)12-19(18)23)20(25-9-8-24-13-25)27-11-10-26-17-5-2-15(21)3-6-17/h2-9,12-13H,10-11H2,1H3/b20-14-
SMILES Code: C/C(C1=CC=C(Cl)C=C1Cl)=C(N2C=CN=C2)/OCCOC3=CC=C(Cl)C=C3
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 423.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Hashiguchi T, Ryu A, Itoyama T, Uchida K, Yamaguchi H. Study of the effective dose of a topical antifungal agent, omoconazole nitrate, on the basis of percutaneous pharmacokinetics in guinea-pigs and mice. J Pharm Pharmacol. 1997 Aug;49(8):757-61. doi: 10.1111/j.2042-7158.1997.tb06107.x. PMID: 9379351.
2: Itoyama T, Uchida K, Yamaguchi H. Therapeutic effects of omoconazole nitrate on guinea-pigs experimentally infected with Trichophyton mentagrophytes. J Antimicrob Chemother. 1997 Jun;39(6):825-7. doi: 10.1093/jac/39.6.825. PMID: 9222056.
3: Fromtling RA. Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. doi: 10.1128/cmr.1.2.187. PMID: 3069196; PMCID: PMC358042.
4: Itoyama T, Uchida K, Yamaguchi H, Fujita S. Therapeutic effects of omoconazole nitrate on experimental tinea pedis, an intractable dermatophytosis, in guinea-pigs. J Antimicrob Chemother. 1997 Sep;40(3):441-4. doi: 10.1093/jac/40.3.441. PMID: 9338501.
5: Nishiyama Y, Itoyama T, Yamaguchi H. Ultrastructural alterations of Candida albicans induced by a new imidazole antimycotic omoconazole nitrate. Microbiol Immunol. 1997;41(5):395-402. doi: 10.1111/j.1348-0421.1997.tb01870.x. PMID: 9194038.
6: Babazadeh-Qazijahani M, Badali H, Irannejad H, Afsarian MH, Emami S. Imidazolylchromanones containing non-benzylic oxime ethers: synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii. Eur J Med Chem. 2014 Apr 9;76:264-73. doi: 10.1016/j.ejmech.2014.02.019. Epub 2014 Feb 11. PMID: 24583607.
7: Uchida K, Itoyama T, Yamaguchi H. [In vitro antifungal activity of omoconazole nitrate, a novel imidazone antimycotic drug, against clinical isolates from patients with cutaneous mycosis]. Jpn J Antibiot. 1996 Aug;49(8):818-23. Japanese. PMID: 9053537.
8: Mosse M, Alric MP, Berceaux M, Fourcine N, Salhi A. Etude comparative de l'activité fongistatique in vitro de l'omoconazole et de six autres imidazolés sur les levures [Comparative study of the fungistatic activity in vitro of omoconazole and 6 other imidazoles against yeasts]. Pathol Biol (Paris). 1986 Jun;34(5 Pt 2):684-7. French. PMID: 3534768.
9: Wang L, Yang W, Wang K, Zhu J, Shen F, Hu Y. Synthesis and biological evaluation of vinyl ether-containing azole derivatives as inhibitors of Trichophyton rubrum. Bioorg Med Chem Lett. 2012 Jul 15;22(14):4887-90. doi: 10.1016/j.bmcl.2012.05.070. Epub 2012 May 24. PMID: 22683344.
10: Zirngibl L, Fischer J, Jahn U, Thiele K. Structure-activity relationships of 2-(1H-imidazol-1-yl)vinyl ethers. Route to the new broad-spectrum antifungal agent omoconazole. Ann N Y Acad Sci. 1988;544:63-73. doi: 10.1111/j.1749-6632.1988.tb40389.x. PMID: 3214095.
