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Merck

D2521

(+)-cis-Diltiazem hydrochloride

≥99% (HPLC), L-type Ca2+ channel blocker, powder

Synonym(s):

(2S,3S)-(+)-cis-3-Acetoxy-5-(2-dimethylaminoethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride, CRD-401

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About This Item

Empirical Formula (Hill Notation):
C22H26N2O4S · HCl
CAS Number:
33286-22-5
Molecular Weight:
450.98
NACRES:
NA.77
PubChem Substance ID:
24277849
UNSPSC Code:
12352200
EC Number:
251-443-3
MDL number:
MFCD00069252
Beilstein/REAXYS Number:
4228706

Product Name

(+)-cis-Diltiazem hydrochloride, ≥99% (HPLC)

InChI key

HDRXZJPWHTXQRI-BHDTVMLSSA-N

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 string

Cl.COc1ccc(cc1)[C@@H]2Sc3ccccc3N(CCN(C)C)C(=O)[C@@H]2OC(C)=O

assay

≥99% (HPLC)

form

powder

originator

Valeant

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779)

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Application

(+)-cis-Diltiazem hydrochloride has been used:
  • to study its effects on diffusion and release in monolithic dispersion matrix(26)
  • to study its neuroprotective effects in retinitis pigmentosa (RP) models(27)
  • as an antagonist against the Cav1.2 L-type calcium channels (LTCCs)(28)

Biochem/physiol Actions

Blocks slow, or L-type Ca2+ channels; regulates Ca2+ release from intracellular stores in neutrophils; stimulates 1,4-dihydropyridine binding to Ca2+ channels; coronary vasodilator.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Calcium Channels and Cyclic Nucleotide-Gated (CNG) and Hyperpolarization Activated Cyclic Nucleotide-Gated (HCN) Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Valeant. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

Diltiazem hydrochloride is used to treat cardiovascular diseases, such as angina and hypertension. It acts as an inhibitor to cytochrome P450 3A (CYP3A). Diltiazem might be associated with maculopapular rashes, urticaria and pruritus.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS7076
MKCM1124
MKCD7486
MKBW4898V
MKBQ8110V

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Diltiazem induces severe photodistributed hyperpigmentation: case series, histoimmunopathology, management, and review of the literature
Saladi RN, et al.
Archives of Dermatology, 142(2), 206-210 (2006)
D Dobrev et al.
British journal of pharmacology, 127(2), 576-582 (1999-06-29)
1. The putative inhibitory effects of verapamil and diltiazem on neuronal non-L-type Ca2+ channels were studied by investigating their effects on either K+- or veratridine-evoked [3H]-dopamine ([3H]-DA) release in rat striatal slices. Involvement of N-, P- and Q-type channels was
Effect of diltiazem on midazolam and alfentanil disposition in patients undergoing coronary artery bypass grafting
Ahonen J, et al.
Anesthesiology, 85(6), 1246-1252 (1996)
Determination of plasma protein binding of diltiazem in horses by ultrafiltration.
C C Schwarzwald et al.
Journal of veterinary pharmacology and therapeutics, 29(6), 579-580 (2006-11-07)
Andrés Pizzorno et al.
Cell reports. Medicine, 1(4), 100059-100059 (2020-08-25)
In the current COVID-19 pandemic context, proposing and validating effective treatments represents a major challenge. However, the scarcity of biologically relevant pre-clinical models of SARS-CoV-2 infection imposes a significant barrier for scientific and medical progress, including the rapid transition of
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