Oxiconazole | CAS#64211-46-7

MedKoo Cat#: 318399 | Name: Oxiconazole nitrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxiconazole is an antifungal medication typically administered in a cream or lotion to treat skin infections, such as athlete's foot, jock itch and ringworm. It can also be prescribed to treat the skin rash known as tinea versicolor, caused by systemic yeast overgrowth (Candida spp.).

Chemical Structure

Oxiconazole nitrate

CAS#64211-46-7 (nitrate)

Theoretical Analysis

MedKoo Cat#: 318399

Name: Oxiconazole nitrate

CAS#: 64211-46-7 (nitrate)

Chemical Formula: C18H14Cl4N4O4

Exact Mass:

Molecular Weight: 492.14

Elemental Analysis: C, 43.93; H, 2.87; Cl, 28.82; N, 11.38; O, 13.00

Price and Availability

Size	Price	Availability	Quantity
1g	USD 350.00
5g	USD 650.00
10g	USD 950.00
20g	USD 1,650.00
50g	USD 2,950.00

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Related CAS #

64211-45-6 (free base) 64211-46-7 (nitrate)

Synonym

Oxiconazole, Oxistat, Oxizole, Fonx, Myfungar; Ro 13-8996; Ro-13-8996; Ro13-8996; Sgd 301-76; ST 813; ST-813; ST813;

IUPAC/Chemical Name

(Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine;nitric acid

InChi Key

WVNOAGNOIPTWPT-NDUABGMUSA-N

InChi Code

InChI=1S/C18H13Cl4N3O.HNO3/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;2-1(3)4/h1-8,11H,9-10H2;(H,2,3,4)/b24-18+;

SMILES Code

C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]

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, not in water

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxiconazole (Ro 13-8996) nitrate is a broad spectrum anti-fungal agent and is also a highly efficacious activator of CYP3A4 transactivation.

In vitro activity:

The present study examined effects of azole antimycotics clotrimazole, ketoconazole, econazole, oxiconazole, miconazole, fluconazole, and itraconazole on PXR-mediated expression of CYP3A4. This study shows that oxiconazole is a highly efficacious activator of CYP3A4 transactivation, which could be antagonized by rifampicin in a competitive manner. Reference: Drug Metab Dispos. 2008 Feb;36(2):339-48. https://pubmed.ncbi.nlm.nih.gov/17998298/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	40.64
	DMSO	62.5	127.00
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.61
	Ethanol	3.0	6.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 492.14 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

Formulation protocol:

1. Shi J, Zhou L, Huang HS, Peng L, Xie N, Nice E, Fu L, Jiang C, Huang C. Repurposing Oxiconazole against Colorectal Cancer via PRDX2-mediated Autophagy Arrest. Int J Biol Sci. 2022 May 21;18(9):3747-3761. doi: 10.7150/ijbs.70679. PMID: 35813474; PMCID: PMC9254464. 2. Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P. Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. doi: 10.1124/dmd.107.018341. Epub 2007 Nov 12. PMID: 17998298.

In vitro protocol:

In vivo protocol:

TBD

1: Özdemir S, Tuncer Ü, Tarkan Ö, Akar F, Sürmelioğlu Ö. Effects of topical oxiconazole and boric acid in alcohol solutions to rat inner ears. Otolaryngol Head Neck Surg. 2013 Jun;148(6):1023-7. doi: 10.1177/0194599813481565. Epub 2013 Mar 12. PubMed PMID: 23482479. 2: Aydın E, Taştan E, Aydoǧan F, Karaca G, Asım Şafak M. Ototoxic effect of topical oxiconazole and terbinafine in rats. J Otolaryngol Head Neck Surg. 2012 Apr;41(2):78-83. PubMed PMID: 22569007. 3: Verma A, Srivastava S, Sane SA, Marrapu VK, Srinivas N, Yadav M, Bhandari K, Gupta S. Antileishmanial activity of benzocycloalkyl azole oximino ethers: the conformationally constraint analogues of oxiconazole. Acta Trop. 2011 Feb;117(2):157-60. doi: 10.1016/j.actatropica.2010.10.011. Epub 2010 Nov 13. PubMed PMID: 21078278. 4: Milanese L, Giacchè N, Schiaffella F, Vecchiarelli A, Macchiarulo A, Fringuelli R. Oxime and oxime ether derivatives of 1,4-benzothiazine related to oxiconazole. ChemMedChem. 2007 Aug;2(8):1208-13. PubMed PMID: 17541993. 5: Milano J, Cardoso SG. Spectrophotometric determination of oxiconazole in topical lotion using methyl orange. J Pharm Biomed Anal. 2005 Apr 1;37(4):639-42. Epub 2004 Dec 21. PubMed PMID: 15797782. 6: Milano J, Morsch LM, Cardoso SG. LC method for the analysis of Oxiconazole in pharmaceutical formulations. J Pharm Biomed Anal. 2002 Sep 5;30(2):175-80. PubMed PMID: 12191701. 7: Ablon G, Rosen T, Spedale J. Comparative efficacy of naftifine, oxiconazole, and terbinafine in short-term treatment of tinea pedis. Int J Dermatol. 1996 Aug;35(8):591-3. PubMed PMID: 8854165. 8: Jegasothy BV, Pakes GE. Oxiconazole nitrate: pharmacology, efficacy, and safety of a new imidazole antifungal agent. Clin Ther. 1991 Jan-Feb;13(1):126-41. Review. PubMed PMID: 2029718. 9: Wu SX, Shen YN, Yan N, Guo NR, Liu LL, Yang JQ. Experimental and clinical investigation on oxiconazole. Chin Med J (Engl). 1989 Aug;102(8):644-6. PubMed PMID: 2517622. 10: Raulin C, Frosch PJ. Contact allergy to oxiconazole. Contact Dermatitis. 1987 Jan;16(1):39-40. PubMed PMID: 3816206. 11: Ramelet AA, Walker-Nasir E. One daily application of oxiconazole cream is sufficient for treating dermatomycoses. Dermatologica. 1987;175(6):293-5. PubMed PMID: 3319722. 12: Wagner W. [Comparison of clinical efficacy and tolerance of oxiconazole administered 1 x daily or 2 x daily]. Mykosen. 1986 Jun;29(6):280-4. German. PubMed PMID: 3762589. 13: Polak-Wyss A, Lengsfeld H, Oesterhelt G. Effect of oxiconazole and Ro 14-4767/002 on sterol pattern in Candida albicans. Sabouraudia. 1985 Dec;23(6):433-41. PubMed PMID: 3913013. 14: Stüttgen G, Bauer E. [Permeation of labeled Oxiconazole. Comparison between the autoradiographic and horizontal slice technics with human skin]. Mykosen. 1985 Mar;28(3):138-47. German. PubMed PMID: 3990703. 15: Gip L. Comparison of oxiconazole (Ro 13-8996) and econazole in dermatomycoses. Mykosen. 1984 Jun;27(6):295, 298-302. PubMed PMID: 6382000. 16: Gebhart RJ, Espinel-Ingroff A, Shadomy S. In vitro susceptibility studies with oxiconazole (Ro 13-8996). Chemotherapy. 1984;30(4):244-7. PubMed PMID: 6086246. 17: Timm U, Zell M, Herzfeld L. Sensitive gas-liquid chromatographic method for the determination of oxiconazole in plasma. J Chromatogr. 1982 Apr 16;229(1):111-20. PubMed PMID: 7085818. 18: Polak A. Oxiconazole, a new imidazole derivative. Evaluation of antifungal activity in vitro and in vivo. Arzneimittelforschung. 1982;32(1):17-24. PubMed PMID: 7037014. 19: Bhandari K, Srinivas N, Shiva Keshava GB, Shukla PK. Tetrahydronaphthyl azole oxime ethers: the conformationally rigid analogues of oxiconazole as antibacterials. Eur J Med Chem. 2009 Jan;44(1):437-47. doi: 10.1016/j.ejmech.2008.01.006. Epub 2008 Jan 25. PubMed PMID: 18313805. 20: Pereiro MJ, Iglesias-Grobas A, Pérez JT. [In vitro comparison of antifungal activity of oxiconazole and econazole against yeast.]. Rev Iberoam Micol. 1998 Jun;15(2):75-7. Spanish. PubMed PMID: 17655413.