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Merck
CN

381195

Sigma-Aldrich

Verapamil hydrochloride

98%

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
EC Number:
205-800-5
MDL number:
MFCD00055208
UNSPSC Code:
12352203
PubChem Substance ID:
24863792

Key Documents

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Assay

98%

mp

142 °C (dec.) (lit.)

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

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Biochem/physiol Actions

α1-adrenoceptor antagonist; L-type calcium channel blocker.
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.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
05902KH
09716AZ
12731MA
07214AA

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Françoise Nepveu et al.
Journal of medicinal chemistry, 53(2), 699-714 (2009-12-18)
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), as well as for
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
Shashank Gupta et al.
American journal of respiratory and critical care medicine, 188(5), 600-607 (2013-06-29)
A major priority in tuberculosis (TB) is to reduce effective treatment times and emergence of resistance. Recent studies in macrophages and zebrafish show that inhibition of mycobacterial efflux pumps with verapamil reduces the bacterial drug tolerance and may enhance drug
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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