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PHR1131

Supelco

(±)-Verapamil hydrochloride

Pharmaceutical Secondary Standard; Certified Reference Material

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Synonym(s):
5-[N-(3,4-Dimethoxyphenylethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride
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
PubChem Substance ID:
329823152
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

Agency

traceable to Ph. Eur. V0100000
traceable to USP 1711202

API family

verapamil

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

142 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°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

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Verapamil hydrochloride is a calcium channel blocker used commonly for the management of angina, supra-ventricular tachyarrhythmia, hypertension, migraine and atrial tachyarrhythmias.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Verapamil hydrochloride may be used as a pharmaceutical reference standard for the determination of the analyte in drug raw material and pharmaceutical formulations by high performance liquid chromatography and spectrophotometric method, respectively.

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.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA5980 in the slot below. This is an example certificate only and may not be the lot that you receive.

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

Certificates of Analysis (COA)

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Spectrophotometric method for the determination of verapamil hydrochloride in pharmaceutical formulations using N-bromosuccinimide as oxidant
Rahman N et al.
Il Farmaco (Societa Chimica Italiana : 1989), 59(7), 529-536 (2004)
Overdose of sustained-release verapamil
Barrow PM, et al.
British journal of anaesthesia, 72(3), 361-365 (1994)
High-performance liquid chromatographic method for the assay of verapamil hydrochloride and related compounds in raw material
Lacroix PM, et al.
Journal of Pharmaceutical and Biomedical Analysis, 9(10-12), 817-822 (1991)
Irena Roci et al.
Cell cycle (Georgetown, Tex.), 19(20), 2676-2684 (2020-10-06)
Proliferating cells must synthesize a wide variety of macromolecules while progressing through the cell cycle, but the coordination between cell cycle progression and cellular metabolism is still poorly understood. To identify metabolic processes that oscillate over the cell cycle, we
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
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Protocols

LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

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