Keto-itraconazole | CAS#112560-33-5 | metabolite

MedKoo Cat#: 558356 | Name: Keto-itraconazole

Description:

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

Keto-itraconazole is a metabolite of Itraconazole.

Chemical Structure

Keto-itraconazole

CAS#112560-33-5

Theoretical Analysis

MedKoo Cat#: 558356

Name: Keto-itraconazole

CAS#: 112560-33-5

Chemical Formula: C35H36Cl2N8O5

Exact Mass: 718.2200

Molecular Weight: 719.62

Elemental Analysis: C, 58.42; H, 5.04; Cl, 9.85; N, 15.57; O, 11.12

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Synonym

Keto-itraconazole; Keto itraconazole; Ketoitraconazole;

IUPAC/Chemical Name

4-(4-(4-(4-(((2S,4R)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(3-oxobutan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one

InChi Key

GZEZATDDANETAV-CEAPFGRNSA-N

InChi Code

InChI=1S/C35H36Cl2N8O5/c1-24(25(2)46)45-34(47)44(23-40-45)29-6-4-27(5-7-29)41-13-15-42(16-14-41)28-8-10-30(11-9-28)48-18-31-19-49-35(50-31,20-43-22-38-21-39-43)32-12-3-26(36)17-33(32)37/h3-12,17,21-24,31H,13-16,18-20H2,1-2H3/t24?,31-,35-/m1/s1

SMILES Code

O=C1N(C(C(C)=O)C)N=CN1C2=CC=C(N3CCN(C4=CC=C(OC[C@H]5O[C@@](C6=CC=C(Cl)C=C6Cl)(CN7N=CN=C7)OC5)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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 719.62 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: Liang X, Van Parys M, Ding X, Zeng N, Bi L, Dorshort D, McKnight J, Milanowski D, Mao J, Chen Y, Ware JA, Dean B, Hop CE, Deng Y. Simultaneous determination of itraconazole, hydroxy itraconazole, keto itraconazole and N-desalkyl itraconazole concentration in human plasma using liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 1;1020:111-9. doi: 10.1016/j.jchromb.2016.03.039. Epub 2016 Mar 26. PubMed PMID: 27038403. 2: Liang X, Van Parys M, Ding X, Zeng N, Bi L, Dorshorst D, McKnight J, Milanowski D, Mao J, Chen Y, Ware JA, Dean B, Hop CECA, Deng Y. Corrigendum to "Simultaneous determination of itraconazole, hydroxy itraconazole, keto itraconazole and N-desalkyl itraconazole concentration in human plasma using liquid chromatography with tandem mass spectrometry" [J. Chromatogr. B 1020 (2016) 111-119]. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Sep 1;1029-1030:239. doi: 10.1016/j.jchromb.2016.06.023. Epub 2016 Jul 16. PubMed PMID: 27475407. 3: Mino Y, Naito T, Watanabe T, Yamada T, Yagi T, Yamada H, Kawakami J. Hydroxy-itraconazole pharmacokinetics is similar to that of itraconazole in immunocompromised patients receiving oral solution of itraconazole. Clin Chim Acta. 2013 Jan 16;415:128-32. doi: 10.1016/j.cca.2012.10.028. Epub 2012 Oct 23. PubMed PMID: 23089073. 4: Mino Y. [Optimization of Immunosuppression and the Prevention of Fungal Infection in Autoimmune Diseases]. Yakugaku Zasshi. 2015;135(10):1123-7. doi: 10.1248/yakushi.15-00193. Review. Japanese. PubMed PMID: 26423867. 5: Isoherranen N, Kunze KL, Allen KE, Nelson WL, Thummel KE. Role of itraconazole metabolites in CYP3A4 inhibition. Drug Metab Dispos. 2004 Oct;32(10):1121-31. Epub 2004 Jul 8. PubMed PMID: 15242978. 6: Templeton IE, Thummel KE, Kharasch ED, Kunze KL, Hoffer C, Nelson WL, Isoherranen N. Contribution of itraconazole metabolites to inhibition of CYP3A4 in vivo. Clin Pharmacol Ther. 2008 Jan;83(1):77-85. Epub 2007 May 9. PubMed PMID: 17495874; PubMed Central PMCID: PMC3488349.