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D2521

Sigma-Aldrich

(+)-cis-Diltiazem hydrochloride

≥99% (HPLC)

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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
Empirical Formula (Hill Notation):
C22H26N2O4S · HCl
CAS Number:
33286-22-5
Molecular Weight:
450.98
Beilstein:
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

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
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)
Selina M Garcia et al.
PloS one, 15(7), e0236288-e0236288 (2020-07-24)
Although voltage-gated Ca2+ channels (VGCC) are a major Ca2+ entry pathway in vascular smooth muscle cells (VSMCs), several other Ca2+-influx mechanisms exist and play important roles in vasoreactivity. One of these is store-operated Ca2+ entry (SOCE), mediated by an interaction
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