WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H558356
CAS#: 112560-33-5
Description: Keto-itraconazole is a metabolite of Itraconazole.
Hodoodo Cat#: H558356
Name: Keto-itraconazole
CAS#: 112560-33-5
Chemical Formula: C35H36Cl2N8O5
Exact Mass: 718.22
Molecular Weight: 719.620
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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
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 |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
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.