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D2521

(+)-cis-Diltiazem hydrochloride

Name: (+)-<I>cis</I>-Diltiazem hydrochloride
Brand: SIGMA

≥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

Assay:

≥99% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

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

Quality Level

200

assay

≥99% (HPLC)

form

powder

originator

Valeant

storage temp.

2-8°C

SMILES string

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

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

InChI key

HDRXZJPWHTXQRI-BHDTVMLSSA-N

Gene Information

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

Description

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.

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.

Other Notes

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

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 + P330 - P501

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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Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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)

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)

The effects of verapamil and diltiazem on N-, P- and Q-type calcium channels mediating dopamine release in rat striatum.

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

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Global Trade Item Number

SKU	GTIN
D2521-10G	04061832961521
D2521-1G	04061835506217
D2521-5G	04061833562345