Diltiazem HCl | CAS#33286-22-5 | L-type Ca channel blocker | CNG channel blocker

MedKoo Cat#: 540110 | Name: Diltiazem HCl

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Description:

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

Diltiazem HCl is an L-type Ca channel blocker and potential CNG channel blocker used to treat hypertension, angina, and arrhythmia. It also prevents formation of aortic aneurysms and limits desphosphorylation of connexin43 gap junction proteins in ischemia/reperfusion models.

Chemical Structure

Diltiazem HCl

CAS#33286-22-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 540110

Name: Diltiazem HCl

CAS#: 33286-22-5 (HCl)

Chemical Formula: C22H27ClN2O4S

Exact Mass: 0.0000

Molecular Weight: 450.97

Elemental Analysis: C, 58.59; H, 6.03; Cl, 7.86; N, 6.21; O, 14.19; S, 7.11

Price and Availability

Size	Price	Availability
1g	USD 150.00	2 weeks
2g	USD 225.00	2 weeks
5g	USD 485.00	2 weeks
10g	USD 850.00	2 weeks

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Related CAS #

42399-41-7 (free base) 144604-00-2 (malate) 33286-22-5 (HCl) 139492-78-7 (maleate)

Synonym

Diltiazem HCl; CRD-401; CRD401; CRD 401; Tiazac; Dilzene

IUPAC/Chemical Name

(2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate hydrochloride

InChi Key

HDRXZJPWHTXQRI-BHDTVMLSSA-N

InChi Code

InChI=1S/C22H26N2O4S.ClH/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3;/h5-12,20-21H,13-14H2,1-4H3;1H/t20-,21+;/m1./s1

SMILES Code

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

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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Diltiazem hydrochloride is a Ca2+ influx inhibitor (slow channel blocker or calcium antagonist).

In vitro activity:

Treatment with diltiazem inhibited the proliferation and suppressed the mobility of MHCC97H and 7402 cells in a time- and concentration-dependent manner (P < 0.05). Treatment with 100 μmol/L diltiazem for 24 h significantly inhibited the proliferation of MHCC97H cells and down-regulated the mRNA and protein levels of TMEM16A. In 7402 cells, diltiazem treatment at 50 μmol/L for 48 h resulted in the most significant inhibitory effect on the cell proliferation and TMEM16A expressions. The results suggest that diltiazem can transiently inhibit the invasion of hepatocellular carcinoma cells in vitro possibly by down-regulating the expression of TMEM16A at both the mRNA and protein levels. Reference: Nan Fang Yi Ke Da Xue Xue Bao. 2018 Jul 30;38(7):818-823. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6765537/

In vivo activity:

The hypothesis that the calcium ion (Ca2+ ) channel blocker diltiazem (DTZ) reduces contraction-induced skeletal muscle damage was tested in B6.A-Dysfprmd /GeneJ (BLAJ) mice, which model human limb-girdle muscular dystrophy 2B (LGMD2B). DTZ improved contractile torque before and immediately after forced eccentric contractions, but did not reduce delayed-onset muscle damage that was observed at 3 days after eccentric contractions. Reference: Physiol Rep. 2018 Jun;6(11):e13727. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5995314/

	Solvent	mg/mL	mM
Solubility
	DMSO	48.0	106.44
	H2O	62.0	137.48

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 450.97 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:

1. Guo R, Huang X, Jin X, Yang J. [Diltiazem inhibits proliferation and motility of hepatocellular cells in vitro by downregulating calcium-activated chloride channel TMEM16A]. Nan Fang Yi Ke Da Xue Xue Bao. 2018 Jul 30;38(7):818-823. Chinese. doi: 10.3969/j.issn.1673-4254.2018.07.08. PMID: 33168514; PMCID: PMC6765537. 2. Watts TJ. The in vitro hemolytic effect of diltiazem on erythrocytes exposed to varying osmolarity. Toxicol Mech Methods. 2010 Oct;20(8):435-9. doi: 10.3109/15376516.2010.491519. PMID: 20486888. 3. Begam M, Collier AF, Mueller AL, Roche R, Galen SS, Roche JA. Diltiazem improves contractile properties of skeletal muscle in dysferlin-deficient BLAJ mice, but does not reduce contraction-induced muscle damage. Physiol Rep. 2018 Jun;6(11):e13727. doi: 10.14814/phy2.13727. PMID: 29890050; PMCID: PMC5995314. 4. Westermann D, Knollmann BC, Steendijk P, Rutschow S, Riad A, Pauschinger M, Potter JD, Schultheiss HP, Tschöpe C. Diltiazem treatment prevents diastolic heart failure in mice with familial hypertrophic cardiomyopathy. Eur J Heart Fail. 2006 Mar;8(2):115-21. doi: 10.1016/j.ejheart.2005.07.012. Epub 2005 Oct 7. PMID: 16214409.

In vitro protocol:

In vivo protocol:

1. Begam M, Collier AF, Mueller AL, Roche R, Galen SS, Roche JA. Diltiazem improves contractile properties of skeletal muscle in dysferlin-deficient BLAJ mice, but does not reduce contraction-induced muscle damage. Physiol Rep. 2018 Jun;6(11):e13727. doi: 10.14814/phy2.13727. PMID: 29890050; PMCID: PMC5995314. 2. Westermann D, Knollmann BC, Steendijk P, Rutschow S, Riad A, Pauschinger M, Potter JD, Schultheiss HP, Tschöpe C. Diltiazem treatment prevents diastolic heart failure in mice with familial hypertrophic cardiomyopathy. Eur J Heart Fail. 2006 Mar;8(2):115-21. doi: 10.1016/j.ejheart.2005.07.012. Epub 2005 Oct 7. PMID: 16214409.

1: Mokhtar Ibrahim M, Tawfique SA, Mahdy MM. Liposomal diltiazem HCl as ocular drug delivery system for glaucoma. Drug Dev Ind Pharm. 2014 Jun;40(6):765-73. doi: 10.3109/03639045.2013.783589. Epub 2013 Apr 9. PubMed PMID: 23570512. 2: Shojaee S, Asare-Addo K, Kaialy W, Nokhodchi A, Cumming I. An investigation into the stabilization of diltiazem HCl release from matrices made from aged polyox powders. AAPS PharmSciTech. 2013 Sep;14(3):1190-8. doi: 10.1208/s12249-013-0013-7. Epub 2013 Jul 31. PubMed PMID: 23900884; PubMed Central PMCID: PMC3755153. 3: Raut Desai S, Rohera BD. Formulation, in vitro evaluation and study of variables on tri-layered gastro-retentive delivery system of diltiazem HCl. Drug Dev Ind Pharm. 2014 Mar;40(3):380-9. doi: 10.3109/03639045.2012.763138. Epub 2013 Feb 1. PubMed PMID: 23369093. 4: Qazi F, Shoaib MH, Yousuf RI, Qazi TM, Mehmood ZA, Hasan SM. Formulation development and evaluation of Diltiazem HCl sustained release matrix tablets using HPMC K4M and K100M. Pak J Pharm Sci. 2013 Jul;26(4):653-63. PubMed PMID: 23811439. 5: Silva SM, Hu L, Sousa JJ, Pais AA, Michniak-Kohn BB. A combination of nonionic surfactants and iontophoresis to enhance the transdermal drug delivery of ondansetron HCl and diltiazem HCl. Eur J Pharm Biopharm. 2012 Apr;80(3):663-73. doi: 10.1016/j.ejpb.2011.11.010. Epub 2011 Nov 25. PubMed PMID: 22137964. 6: Cetin EO, Gundogdu E, Kirilmaz L. Novel microparticle drug delivery systems based on chitosan and Eudragit® RSPM to enhance diltiazem hydrochloride release property. Pharm Dev Technol. 2012 Nov-Dec;17(6):741-6. doi: 10.3109/10837450.2011.580759. Epub 2011 May 13. PubMed PMID: 21563988. 7: Al-Zoubi N, Al-Obaidi G, Tashtoush B, Malamataris S. Sustained release of diltiazem HCl tableted after co-spray drying and physical mixing with PVAc and PVP. Drug Dev Ind Pharm. 2016;42(2):270-9. doi: 10.3109/03639045.2015.1047848. Epub 2015 Jun 2. PubMed PMID: 26035331. 8: Bettini R, Bonferoni MC, Colombo P, Zanelotti L, Caramella C. Drug release kinetics and front movement in matrix tablets containing diltiazem or metoprolol/λ-carrageenan complexes. Biomed Res Int. 2014;2014:671532. doi: 10.1155/2014/671532. Epub 2014 Jun 19. PubMed PMID: 25045689; PubMed Central PMCID: PMC4090483. 9: Yang XS, Li QL, Rong K. [A comparison between diltiazem SR and diltiazem HCL in the treatment of angina pectoris]. Zhonghua Nei Ke Za Zhi. 1993 Jan;32(1):31-2. Chinese. PubMed PMID: 8404314. 10: Kaialy W, Bello H, Asare-Addo K, Nokhodchi A. Effect of solvent on retarding the release of diltiazem HCl from Polyox-based liquisolid tablets. J Pharm Pharmacol. 2016 Nov;68(11):1396-1402. doi: 10.1111/jphp.12643. Epub 2016 Oct 7. PubMed PMID: 27714817. 11: Yusif RM, Abu Hashim II, El-Dahan MS. Some variables affecting the characteristics of Eudragit E-sodium alginate polyelectrolyte complex as a tablet matrix for diltiazem hydrochloride. Acta Pharm. 2014 Mar;64(1):89-104. doi: 10.2478/acph-2014-0010. PubMed PMID: 24670354. 12: Nguyen CN, Christensen JM, Ayres JW. Formulation of sustained-release verapamil HCl and diltiazem HCl semisolid matrix capsules. Pharm Dev Technol. 2008;13(2):115-25. doi: 10.1080/10837450701831070 . PubMed PMID: 18379903. 13: Schaus V. [Topical diltiazem preparations for the treatment of anal fissures]. J Pharm Belg. 2013 Dec;(4):14-7. French. PubMed PMID: 24449968. 14: 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. 15: Karakatsani M, Dedhiya M, Plakogiannis FM. The effect of permeation enhancers on the viscosity and the release profile of transdermal hydroxypropyl methylcellulose gel formulations containing diltiazem HCl. Drug Dev Ind Pharm. 2010 Oct;36(10):1195-206. doi: 10.3109/03639041003695105. PubMed PMID: 20545504. 16: 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. 17: Day RW. Differences in the acute pulmonary vascular effects of oxygen with nitric oxide and diltiazem: implications for the long-term treatment of pulmonary arterial hypertension. Congenit Heart Dis. 2013 Jan-Feb;8(1):71-7. doi: 10.1111/j.1747-0803.2012.00704.x. Epub 2012 Aug 14. PubMed PMID: 22891699. 18: McClelland GA, Sutton SC, Engle K, Zentner GM. The solubility-modulated osmotic pump: in vitro/in vivo release of diltiazem hydrochloride. Pharm Res. 1991 Jan;8(1):88-92. PubMed PMID: 2014214. 19: Ayad MM, Shalaby A, Abdellatef HE, Hosny MM. New colorimetric methods for the determination of trazodone HCl, famotidine, and diltiazem HCl in their pharmaceutical dosage forms. Anal Bioanal Chem. 2003 Jul;376(5):710-4. Epub 2003 May 16. PubMed PMID: 12750873. 20: Maeda K, Takasugi T, Tsukano Y, Tanaka Y, Shiota K. Clinical study on the hypotensive effect of diltiazem hydrochloride. Int J Clin Pharmacol Ther Toxicol. 1981 Feb;19(2):47-55. PubMed PMID: 7216550.