Deacetyldiltiazem | 42399-40-6

MedKoo Cat#: 581573 | Name: Deacetyldiltiazem

Description:

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

Deacetyldiltiazem is a metabolite product of the drug Diltiazem (a coronary vasodilator), and is present in the plasma of individuals taking that medication.

Chemical Structure

Deacetyldiltiazem

CAS#42399-40-6 (free base)

Theoretical Analysis

MedKoo Cat#: 581573

Name: Deacetyldiltiazem

CAS#: 42399-40-6 (free base)

Chemical Formula: C20H24N2O3S

Exact Mass: 372.1508

Molecular Weight: 372.48

Elemental Analysis: C, 64.49; H, 6.49; N, 7.52; O, 12.89; S, 8.61

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Related CAS #

42399-40-6 (free base) 75472-91-2 (HCl)

Synonym

Deacetyldiltiazem; Desacetyl Diltiazem;

IUPAC/Chemical Name

(2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

InChi Key

NZHUXMZTSSZXSB-MOPGFXCFSA-N

InChi Code

InChI=1S/C20H24N2O3S/c1-21(2)12-13-22-16-6-4-5-7-17(16)26-19(18(23)20(22)24)14-8-10-15(25-3)11-9-14/h4-11,18-19,23H,12-13H2,1-3H3/t18-,19+/m1/s1

SMILES Code

O=C1[C@H](O)[C@H](C2=CC=C(OC)C=C2)SC3=CC=CC=C3N1CCN(C)C

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 372.48 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: Kurokawa T, Fukami T, Nakajima M. Characterization of Species Differences in Tissue Diltiazem Deacetylation Identifies Ces2a as a Rat-Specific Diltiazem Deacetylase. Drug Metab Dispos. 2015 Aug;43(8):1218-25. doi: 10.1124/dmd.115.064089. Epub 2015 May 15. PubMed PMID: 25979260. 2: Qiang F, Kang KW, Han HK. Repeated dosing of piperine induced gene expression of P-glycoprotein via stimulated pregnane-X-receptor activity and altered pharmacokinetics of diltiazem in rats. Biopharm Drug Dispos. 2012 Nov;33(8):446-54. doi: 10.1002/bdd.1811. Epub 2012 Sep 18. PubMed PMID: 22927137. 3: Choi DH, Choi JS, Li C, Choi JS. Effects of simvastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, after oral and intravenous administration in rats: possible role of P-glycoprotein and CYP3A4 inhibition by simvastatin. Pharmacol Rep. 2011;63(6):1574-82. PubMed PMID: 22358108. 4: Hong SP, Yang JS, Han JY, Ha SI, Chung JW, Koh YY, Chang KS, Choi DH. Effects of lovastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats: possible role of cytochrome P450 3A4 and P-glycoprotein inhibition by lovastatin. J Pharm Pharmacol. 2011 Jan;63(1):129-35. PubMed PMID: 21189658. 5: Bertrand N, Bouvet C, Moreau P, Leroux JC. Transmembrane pH-gradient liposomes to treat cardiovascular drug intoxication. ACS Nano. 2010 Dec 28;4(12):7552-8. doi: 10.1021/nn101924a. Epub 2010 Nov 10. PubMed PMID: 21067150. 6: Cho YA, Choi DH, Choi JS. Effect of hesperidin on the oral pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. J Pharm Pharmacol. 2009 Jun;61(6):825-9. doi: 10.1211/jpp.61.06.0017. PubMed PMID: 19505375. 7: Li C, Choi JS. Effects of epigallocatechin gallate on the bioavailability and pharmacokinetics of diltiazem in rats. Pharmazie. 2008 Nov;63(11):815-8. PubMed PMID: 19069242. 8: Hong SP, Choi DH, Choi JS. Effects of resveratrol on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem, in rats. Cardiovasc Ther. 2008 Winter;26(4):269-75. doi: 10.1111/j.1755-5922.2008.00060.x. PubMed PMID: 19035878. 9: Hong SP, Chang KS, Choi DH, Choi JS. Effect of atorvastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. Arch Pharm Res. 2007 Jan;30(1):90-5. PubMed PMID: 17328247. 10: Choi JS, Han HK. Enhanced oral exposure of diltiazem by the concomitant use of naringin in rats. Int J Pharm. 2005 Nov 23;305(1-2):122-8. Epub 2005 Oct 13. PubMed PMID: 16226412. 11: Choi HJ, Choi JS. Effects of morin pretreatment on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem in rats. Arch Pharm Res. 2005 Aug;28(8):970-6. Retraction in: Choi HJ, Choi JS. Arch Pharm Res. 2006 Oct;29(10):935. PubMed PMID: 16178425. 12: Choi JS, Burm JP. The influence of cimetidine on the pharmacokinetics of diltiazem and its main metabolite in rabbits. Arch Pharm Res. 2004 Feb;27(2):254-8. PubMed PMID: 15022730. 13: Sista S, Lai JC, Eradiri O, Albert KS. Pharmacokinetics of a novel diltiazem HCl extended-release tablet formulation for evening administration. J Clin Pharmacol. 2003 Oct;43(10):1149-57. PubMed PMID: 14517197. 14: Molden E, Johansen PW, Bøe GH, Bergan S, Christensen H, Rugstad HE, Rootwelt H, Reubsaet L, Lehne G. Pharmacokinetics of diltiazem and its metabolites in relation to CYP2D6 genotype. Clin Pharmacol Ther. 2002 Sep;72(3):333-42. PubMed PMID: 12235455. 15: Choi JS, Kim YG. Pharmacokinetic changes of diltiazem and desacetyldiltiazem after oral administration of diltiazem in rabbits with diabetes mellitus induced by alloxan. Biopharm Drug Dispos. 2002 Apr;23(3):115-20. PubMed PMID: 12173546. 16: Rueda S, Fraile LJ, Bregante MA, Garcia MA, Solans C. Penetration of diltiazem into breast milk and its pharmacokinetics in the lactating rabbit. Xenobiotica. 2002 Feb;32(2):119-30. PubMed PMID: 11868968. 17: Molden E, Asberg A, Christensen H. Desacetyl-diltiazem displays severalfold higher affinity to CYP2D6 compared with CYP3A4. Drug Metab Dispos. 2002 Jan;30(1):1-3. PubMed PMID: 11744603. 18: Chankvetadze B, Kartozia I, Blaschke G. Simultaneous enantioseparation of cis-diltiazem hydrochloride and its metabolite cis-desacetyldiltiazem using high-performance liquid chromatography and capillary electrophoresis. J Pharm Biomed Anal. 2002 Jan 1;27(1-2):161-6. PubMed PMID: 11682222. 19: Choi JS, Lee JH, Burm JP. Pharmacokinetics of diltiazem and its major metabolite, deacetyidiltiazem after oral administration of diltiazem in mild and medium folate-induced renal failure rabbits. Arch Pharm Res. 2001 Aug;24(4):333-7. PubMed PMID: 11534767. 20: Fraile LJ, Bregante MA, Garcia MA, Solans C. Development of diltiazem deacetylase and demethylase activities during ontogeny in rabbit. Xenobiotica. 2001 Jul;31(7):409-22. PubMed PMID: 11531005.