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Verapamil hydrochloride

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

(±)-Verapamil hydrochloride, 5-[N-(3,4-Dimethoxyphenylethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride

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About This Item

Linear Formula:
(CH3O)2C6H3CH2CH2N(CH3)(CH2)3C[C6H3(OCH3)2][CH(CH3)2]CN · HCl
CAS Number:
152-11-4
Molecular Weight:
491.06
Beilstein:
3647093
MDL number:
MFCD00055208
UNSPSC Code:
41116107
PubChem Substance ID:
329828921
NACRES:
NA.24

grade

pharmaceutical primary standard

Agency

EP Reference Standard

API family

verapamil

manufacturer/tradename

EDQM

mp

142 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

Cl.COc1ccc(CCN(C)CCCC(C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC

InChI

1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6;/h9-12,17-18,20H,8,13-16H2,1-7H3;1H

InChI key

DOQPXTMNIUCOSY-UHFFFAOYSA-N

Gene Information

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

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Verapamil hydrochloride EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

α1-adrenoceptor antagonist; L-type calcium channel blocker. Blocks L-type Ca2+ channels in smooth and cardiac muscle, induces apoptosis of human primary and metastatic colon adenocarcinoma cells in vitro. Drug resistance reversal agent acting on Pgp, e.g. decrease renal tubule elimination of digoxin. Increases basal ATPase activity of Pgp. Substrate of Cyp3A4 and CYP2C6.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Jian-Min Shen et al.
Pharmacological research, 70(1), 102-115 (2013-02-05)
In this paper we give a method of integrated treatment for cancer and drug-induced complications in the process of cancer therapy through dual-drug delivery system (DDDS). Two hydrophilic drugs, doxorubicin (an antitumor drug) and verapamil (an antiangiocardiopathy drug) combined preliminarily
Rania Soudy et al.
Journal of medicinal chemistry, 56(19), 7564-7573 (2013-09-14)
The efficacy of chemotherapeutic doxorubucin (Dox) in cancer treatment is limited by two main factors, nonspecific toxicity and the emergence of tumor resistance. To overcome these hurdles, in this study peptide-Dox conjugates were prepared. A decapeptide 18-4a (NH₂-WxEAAYQkFL-CONH₂) [corrected] with
Caitrin W McDonough et al.
Hypertension (Dallas, Tex. : 1979), 62(1), 48-54 (2013-05-22)
We sought to identify novel pharmacogenetic markers associated with cardiovascular outcomes in patients with hypertension on antihypertensive therapy. We genotyped a 1:4 case:control cohort (n=1345) on the Illumina HumanCVD Beadchip from the INternational VErapamil SR-Trandolapril STudy (INVEST), where participants were
Novella Calcinaghi et al.
Stroke, 44(7), 1957-1964 (2013-06-06)
Arterial hypertension is an important risk factor for cerebrovascular diseases, such as transient ischemic attacks or stroke, and represents a major global health issue. The effects of hypertension on cerebral blood flow, particularly at the microvascular level, remain unknown. Using
Masato Ishigami et al.
Biochimica et biophysica acta, 1831(4), 683-690 (2013-01-12)
Although human MDR1 and MDR3 share 86% similarity in their amino acid sequences and are predicted to share conserved domains for drug recognition, their physiological transport substrates are quite different: MDR1 transports xenobiotics and confers multidrug resistance, while MDR3 exports
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