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D2521

Sigma-Aldrich

(+)-cis-Diltiazem hydrochloride

≥99% (HPLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C22H26N2O4S · HCl
Número de CAS:
33286-22-5
Peso molecular:
450.98
Beilstein/REAXYS Number:
4228706
EC Number:
251-443-3
MDL number:
MFCD00069252
UNSPSC Code:
12352200
PubChem Substance ID:
24277849
NACRES:
NA.77

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)

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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

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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)
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
M J Gunthorpe et al.
The Journal of physiology, 519 Pt 3, 713-722 (1999-08-24)
1. To extend our knowledge of the site and mechanism of action of L-type Ca2+ channel antagonists on 5-HT3 receptors, whole-cell voltage clamp electrophysiology was used to investigate the action of one of these compounds, diltiazem, on the recombinant receptor
Dong Huang et al.
American heart journal, 164(3), 394-401 (2012-09-18)
No randomized trial has been conducted to compare different vasodilators for treating no-reflow during primary percutaneous coronary intervention (PCI) for ST-segment elevation acute myocardial infarction. The prospective, randomized, 2-center trial was designed to compare the effect of 3 different vasodilators
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