Synonym
Deacylketoconazole; Deacyl ketoconazole; N-Deacetylketoconazole; Deacetylketoconazole; R 39519; R39519; R-39519;
IUPAC/Chemical Name
cis-1-(4-((2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
InChi Key
LOUXSEJZCPKWAX-ZJSXRUAMSA-N
InChi Code
InChI=1S/C24H26Cl2N4O3/c25-18-1-6-22(23(26)13-18)24(16-29-10-7-28-17-29)32-15-21(33-24)14-31-20-4-2-19(3-5-20)30-11-8-27-9-12-30/h1-7,10,13,17,21,27H,8-9,11-12,14-16H2/t21-,24-/m1/s1
SMILES Code
ClC1=CC=C([C@]2(CN3C=CN=C3)OC[C@@H](COC4=CC=C(N5CCNCC5)C=C4)O2)C(Cl)=C1
Purity
>95% (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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
489.40
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 |
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4: Rodriguez RJ, Proteau PJ, Marquez BL, Hetherington CL, Buckholz CJ, O'Connell KL. Flavin-containing monooxygenase-mediated metabolism of N-deacetyl ketoconazole by rat hepatic microsomes. Drug Metab Dispos. 1999 Aug;27(8):880-6. PubMed PMID: 10421614.
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6: Rodriguez RJ, Acosta D Jr. N-deacetyl ketoconazole-induced hepatotoxicity in a primary culture system of rat hepatocytes. Toxicology. 1997 Feb 28;117(2-3):123-31. PubMed PMID: 9057891.
7: Whitehouse LW, Menzies A, Mueller R, Pontefract R. Ketoconazole-induced hepatic phospholipidosis in the mouse and its association with de-N-acetyl ketoconazole. Toxicology. 1994 Nov-Dec;94(1-3):81-95. PubMed PMID: 7801332.
8: Whitehouse LW, Menzies A, Dawson B, Zamecnik J, Sy WW. Deacetylated ketoconazole: a major ketoconazole metabolite isolated from mouse liver. J Pharm Biomed Anal. 1990;8(7):603-6. PubMed PMID: 2100224.
9: Brasseur R, Vandenbosch C, Van den Bossche H, Ruysschaert JM. Mode of insertion of miconazole, ketoconazole and deacylated ketoconazole in lipid layers. A conformational analysis. Biochem Pharmacol. 1983 Jul 15;32(14):2175-80. PubMed PMID: 6307314.
10: Pfaller MA, Segal JJ, Krogstad DJ. Activity of ketoconazole and its deacyl derivative against Plasmodium falciparum and Candida isolates. Antimicrob Agents Chemother. 1982 Nov;22(5):917-9. PubMed PMID: 6295271; PubMed Central PMCID: PMC185686.
