Verapamil hydrochloride
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Verapamil hydrochloride
structure -
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CAS No:
23313-68-0
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Formula:
C27H39ClN2O4
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Chemical Name:
Verapamil hydrochloride
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Synonyms:
CALAN;IPROVERATRIL;(+/-)-5-[N-(3,4-DIMETHOXYPHENYLETHYL)-METHYLAMINO]-2-(3,4-DIMETHOXYPHENYL)-2-ISOPROPYLVALERONITRILE HYDROCHLORIDE;5-[N-(3,4-DIMETHOXYPHENYLETHYL)METHYLAMINO]-2-(3,4-DIMETHOXYPHENYL)-2-ISOPROPYLVALERONITRILE HYDROCHLORIDE;alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-benzeneacetonitrile hydrochloride;ALPHA-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-3,4-DIMETHOXY-ALPHA-(1-METHYLETHYL)BENZENEACETONITRILE HYDROCHLORIDE;5-[(3,4-DIMETHOXYPHENETHYL)METHYLAMINO]-2-(3,4-DIMETHOXYPHENYL)-2-ISOPROPYL-VALERONITRILE HYDROCHLORIDE;(+/-)-VERAPAMIL HYDROCHLORIDE
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Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs
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CAS No:
Description
White Powder
Verapamil hydrochloride (VRP) is a phenylalkylamine calcium ion influx inhibitor (calcium antagonist). Verapamil hydrochloride exerts its pharmacologic effects by modulating the influx of ionic through the slow channels of vascular smooth muscle and cardiac cell membranes. It is widely used for the treatment of hypertension, angina pectoris, supraventricular tachycardia, myocardial infraction, and vascular headaches. Verapamil has also been used in cell biology as an inhibitor of drug efflux pump proteins such as P-glycoprotein, which are often over-expressed in certain tumor cell lines The plasma half-life of verapamil hydrochloride is 2–7 hours, which necessitates multiple dosing. After oral administration of VRP to humans, the drug is rapidly absorbed and widely distributed. It is approximately 90% absorbed from the gastrointestinal tract but is subject to considerable first pass metabolism and its bioavailability is around 20–30%. The low bioavailability is owing to the rapid biotransformation in the liver with a biological half-life of 4.0±1.5 hours.
The salt is purified by dissolving it in EtOH, filtering (if insoluble particles are present) and adding Et2O, filtering the salt, washing it with Et2O and drying it in vacuo. It has the following solubilities: hexane (0.001%), CH2Cl2 (~10%), MeOH (~10%), EtOH (20%) and H2O (8.3%). It has UV max at 232 and 278nm. The free base is a viscous yellow oil b 243-246o/0.01mm (n 25D 1.5448) and is almost insoluble in H2O but soluble in organic solvents. It is a Ca channel antagonist and is a coronary vasodilator. [Ramuz Helv Chim Acta 58 2050 1975, Harvey et al. Biochem J 257 95 1989.]
Characteristics
64
5.89508
white powder
142 °C (dec.)(lit.)
586.1ºC at 760 mmHg
308.3ºC
methanol: 50 mg/mL, clear, colorless
0-6°C
0-6°C
Safety Information
UN 2811 6.1/PG 3
3
T,Xi
36/37-45-37/39-26
YV8320000
T,Xi
P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
23/24/25-36/37/38
UN 2811 6.1/PG 3
Verapamil hydrochloride Use and Manufacturing
Calcium antagonists
A calcium channel blocker. Antihypertensive; antianginal; antiarrhythmic (class IV)
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