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MedKoo Cat#: 461006 | Name: Pramiconazole

Description:

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

Pramiconazole is a triazole antifungal.

Chemical Structure

Pramiconazole
Pramiconazole
CAS#219923-85-0

Theoretical Analysis

MedKoo Cat#: 461006

Name: Pramiconazole

CAS#: 219923-85-0

Chemical Formula: C35H39F2N7O4

Exact Mass: 659.3032

Molecular Weight: 659.73

Elemental Analysis: C, 63.72; H, 5.96; F, 5.76; N, 14.86; O, 9.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Pramiconazole; Azoline; R 126638; R-126638; R126638
IUPAC/Chemical Name
1-(4-(4-(4-(((2S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-4-(2,4-difluorophenyl)-1,3-dioxolan-2-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-3-isopropylimidazolidin-2-one
InChi Key
AEKNYBWUEYNWMJ-QWOOXDRHSA-N
InChi Code
InChI=1S/C35H39F2N7O4/c1-25(2)43-17-18-44(34(43)45)29-6-4-27(5-7-29)40-13-15-41(16-14-40)28-8-10-30(11-9-28)46-20-33-47-22-35(48-33,21-42-24-38-23-39-42)31-12-3-26(36)19-32(31)37/h3-12,19,23-25,33H,13-18,20-22H2,1-2H3/t33-,35+/m0/s1
SMILES Code
O=C1N(C(C)C)CCN1C2=CC=C(N3CCN(C4=CC=C(OC[C@H]5OC[C@](CN6N=CN=C6)(C7=CC=C(F)C=C7F)O5)C=C4)CC3)C=C2
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 659.73 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.

Recalculate based on batch purity %
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: Gupta AK, Foley KA. Antifungal Treatment for Pityriasis Versicolor. J Fungi (Basel). 2015 Mar 12;1(1):13-29. doi: 10.3390/jof1010013. Review. PubMed PMID: 29376896; PubMed Central PMCID: PMC5770013. 2: Gupta AK, Lane D, Paquet M. Systematic review of systemic treatments for tinea versicolor and evidence-based dosing regimen recommendations. J Cutan Med Surg. 2014 Mar-Apr;18(2):79-90. Review. PubMed PMID: 24636433. 3: Gupta AK, Richardson M, Paquet M. Systematic review of oral treatments for seborrheic dermatitis. J Eur Acad Dermatol Venereol. 2014 Jan;28(1):16-26. doi: 10.1111/jdv.12197. Epub 2013 Jun 26. Review. PubMed PMID: 23802806. 4: Donders G, Bellen G, Ausma J, Verguts L, Vaneldere J, Hinoul P, Borgers M, Janssens D. The effect of antifungal treatment on the vaginal flora of women with vulvo-vaginal yeast infection with or without bacterial vaginosis. Eur J Clin Microbiol Infect Dis. 2011 Jan;30(1):59-63. doi: 10.1007/s10096-010-1052-6. Epub 2010 Sep 28. PubMed PMID: 20878199. 5: de Wit K, Paulussen C, Matheeussen A, van Rossem K, Cos P, Maes L. In vitro profiling of pramiconazole and in vivo evaluation in Microsporum canis dermatitis and Candida albicans vaginitis laboratory models. Antimicrob Agents Chemother. 2010 Nov;54(11):4927-9. doi: 10.1128/AAC.00730-10. Epub 2010 Aug 30. PubMed PMID: 20805398; PubMed Central PMCID: PMC2976107. 6: Faergemann J, Todd G, Pather S, Vawda ZF, Gillies JD, Walford T, Barranco C, Quiring JN, Briones M. A double-blind, randomized, placebo-controlled, dose-finding study of oral pramiconazole in the treatment of pityriasis versicolor. J Am Acad Dermatol. 2009 Dec;61(6):971-6. doi: 10.1016/j.jaad.2008.08.033. Epub 2009 Oct 13. PubMed PMID: 19828211. 7: Donders G, Ausma J, Wouters L, Cauwenbergh G, Borgers M, Janssens D. Efficacy of a single oral dose of 200 mg pramiconazole in vulvovaginal yeast infections: an exploratory phase IIa trial. Acta Derm Venereol. 2008;88(5):462-6. doi: 10.2340/00015555-0494. PubMed PMID: 18779883. 8: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 May;30(4):313-31. PubMed PMID: 18773127. 9: Geria AN, Scheinfeld NS. Pramiconazole, a triazole compound for the treatment of fungal infections. IDrugs. 2008 Sep;11(9):661-70. Review. PubMed PMID: 18763217. 10: Decroix J, Ausma J, Cauwenbergh G, Borgers M, Wouters L. The efficacy of oral treatment with pramiconazole in tinea pedis and tinea cruris/corporis: two exploratory phase IIa trials. Br J Dermatol. 2008 Apr;158(4):854-6. doi: 10.1111/j.1365-2133.2007.08420.x. Epub 2008 Jan 30. PubMed PMID: 18241269. 11: Faergemann J, Ausma J, Vandeplassche L, Borgers M. The efficacy of oral treatment with pramiconazole in pityriasis versicolor: a phase II a trial. Br J Dermatol. 2007 Jun;156(6):1385-8. PubMed PMID: 17535237. 12: Piérard GE, Ausma J, Henry F, Vroome V, Wouters L, Borgers M, Cauwenbergh G, Piérard-Franchimont C. A pilot study on seborrheic dermatitis using pramiconazole as a potent oral anti-Malassezia agent. Dermatology. 2007;214(2):162-9. PubMed PMID: 17341867. 13: Ausma J, Pennick G, Bohets H, van de Velde V, Borgers M, Fothergill A. Absence of an active metabolite for the triazole antifungal pramiconazole. Acta Derm Venereol. 2007;87(1):22-6. PubMed PMID: 17225011. 14: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Oct;28(8):533-91. PubMed PMID: 17136234. 15: Faergemann J, Ausma J, Borgers M. In vitro activity of R126638 and ketoconazole against Malassezia species. Acta Derm Venereol. 2006;86(4):312-5. PubMed PMID: 16874415. 16: Piérard-Franchimont C, Ausma J, Wouters L, Vroome V, Vandeplassche L, Borgers M, Cauwenbergh G, Piérard GE. Activity of the triazole antifungal r126638 as assessed by corneofungimetry. Skin Pharmacol Physiol. 2006;19(1):50-6. Epub 2005 Oct 20. PubMed PMID: 16247249. 17: Meerpoel L, Backx LJ, Van der Veken LJ, Heeres J, Corens D, De Groot A, Odds FC, Van Gerven F, Woestenborghs FA, Van Breda A, Oris M, van Dorsselaer P, Willemsens GH, Vermuyten KJ, Marichal PJ, Vanden Bossche HF, Ausma J, Borgers M. Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology. J Med Chem. 2005 Mar 24;48(6):2184-93. PubMed PMID: 15771461. 18: Vanden Bossche H, Ausma J, Bohets H, Vermuyten K, Willemsens G, Marichal P, Meerpoel L, Odds F, Borgers M. The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. Antimicrob Agents Chemother. 2004 Sep;48(9):3272-8. PubMed PMID: 15328084; PubMed Central PMCID: PMC514767. 19: Odds F, Ausma J, Van Gerven F, Woestenborghs F, Meerpoel L, Heeres J, Vanden Bossche H, Borgers M. In vitro and in vivo activities of the novel azole antifungal agent r126638. Antimicrob Agents Chemother. 2004 Feb;48(2):388-91. PubMed PMID: 14742185; PubMed Central PMCID: PMC321549.

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