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(+/-)-Verapamil hydrochloride

(+/-)-Verapamil hydrochloride structure

CAS No:
152-11-4
Formula:
C27H39ClN2O4
Chemical Name:
(+/-)-Verapamil hydrochloride
Synonyms:
R(+)-VERAPAMIL HYDROCHLORIDE;(+)-VERAPAMIL, METHOXY-, HYDROCHLORIDE;manidon;verapamilchloridrate;(+)-METHOXYVERAPAMIL HYDROCHLORIDE;Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl) ethyl]methylamino]propyl]-3,4-dimethoxy -α-(1-methylethyl)-, monohydrochloride;(+/-)-Verapamil hydrochloride;alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-benzeneacetonitrile hydrochloride
Categories:
Organic Chemistry > Amides

Description

Verapamil hydrochloride is a calcium channel antagonist.

A calcium channel blocker that is a class IV anti-arrhythmia agent.

Verapamil HCl (152-11-4) is a clinically useful L-type calcium channel blocker.1 It is also used as an inhibitor of drug efflux pump proteins.2

white to off-white powder

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.

(+/-)-Verapamil hydrochloride Basic Attributes

Molecular Weight：

491.06

Exact Mass：

490.259827

BRN：

3647093

EC Number：

205-800-5

NSC Number：

759589|272366|657799

DSSTox ID：

DTXSID2034095

Color/Form：

white

HScode：

29269090

Characteristics

PSA：

Appearance：

white solid

Density：

1.0596 (rough estimate)

Melting Point：

142 °C (dec.)(lit.)

Boiling Point：

586.1°C at 760 mmHg

Flash Point：

9℃

Refractive Index：

1.6290 (estimate)

Water Solubility：

soluble

Storage Conditions：

Refrigerator (+4°C)

Toxicity：

LD50 in mice, rats (mg/kg): 7.6, 16 i.v.; 68, 107 s.c.; 68, 67 i.p.; 163, 114 orally (Haas, Hrtfelder)

PKA：

8.6(at 25℃)

Collision Cross Section：

208.9 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Critical Temperature & Pressure：

2-8°C

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

T,F

safety instructions：

45-36/37/39-36/37-16

RTECS Number：

YV8320000

Marks：

T,F

Storage features：

Room temperature

Precautionary statement(s)：

P261-P280-P301 + P310-P311

Hazard Statements：

25-23/24/25-39/23/24/25-11

RIDADR：

UN 2811 6.1/PG 3

GHS Classification：

|Danger|H300 (39.49%): Fatal if swallowed [Danger Acute toxicity, oral]|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, and P501|Aggregated GHS information provided by 395 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH：

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)|Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

MeSH Entry Terms：

Calan

(+/-)-Verapamil hydrochloride Use and Manufacturing

Uses

Bromhexine metabolite, sodium channel blocker, decongestent secretolytic agent for respiratory diseases

analgesic, antipyretic

±)-Verapamil hydrochloride is a calcium channel modulator, adrenoceptor antagonist, anti-arrhythmic, cardiac depressant, and coronary vasodilator. It is also a calcium channel-blocker. It acts by inhibiting the slow channel entry of calcium into the cell. It acts by plugging up the channels and limiting the entry of calcium into both smooth muscle cells of arteriolar walls and the cardiac muscle cells at higher doses.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:491.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:13
Exact Mass:490.2598354
Monoisotopic Mass:490.2598354
Topological Polar Surface Area:64
Heavy Atom Count:34
Complexity:606
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Calcium ion blockers, which dilate coronary arteries, reduce ventricular rate, and improve left ventricular diastolic function by regulating the influx of calcium ions, are used to treat angina pectoris, arrhythmias, hypertension, etc.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Verapamil Hydrochloride Injection
Ingredients	This product is a sterile aqueous solution of verapamil hydrochloride. The content of verapamil hydrochloride (C27H38N2O4.HCl) should be 93.0% to 107.0% of the labeled amount.
Indication	1. Phenobarbital may increase the clearance of verapamil. 2. Ramifenamide may significantly reduce the bioavailability of verapamil. 3. Acute studies of healthy volunteers taking cimetidine have mixed results, with the clearance of verapamil decreasing or remaining unchanged. 4. Combination with beta-blockers may enhance the inhibitory effect on atrioventricular conduction. 5. When used in combination with other antihypertensive drugs (such as vasodilators, diuretics, etc.), the antihypertensive effects are additive, and patients receiving such combined treatments should be appropriately monitored. 6. Combination with amiodarone may increase cardiac toxicity. 7. Verapamil may increase the blood concentrations of carbamazepine and cyclosporine. 8. There are reports that verapamil increases the sensitivity of patients to lithium (neurotoxicity), and close monitoring is required when the two drugs are used together. 9. Animal experiments suggest that inhaled anesthetics inhibit cardiovascular activity by reducing calcium influx. When used simultaneously with calcium ion antagonists such as verapamil, the doses of the two drugs need to be carefully adjusted to avoid excessive cardiac inhibition. 10. Avoid using disopyramide at the same time. 11 Neuromuscular blockers: Clinical data and animal experimental studies have shown that verapamil may enhance the activity of neuromuscular blockers. When used in combination, the dose of verapamil or neuromuscular blocker should be reduced. 12 Dantrolene: Two animal experimental studies have shown that the concomitant use of the two drugs can lead to cardiovascular collapse.
Specifications	2ml:5mg

Verapamil Hydrochloride Tablets
Ingredients	The main ingredient and chemical name of this product are: α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-isopropylphenylacetonitrile hydrochloride
Indication	1 Cytotoxic drugs such as cyclophosphamide, vincristine, procarbazine, prednisone, vinblastine, doxorubicin, and cisplatin reduce the absorption of verapamil. 2 Phenobarbital, hydantoin, vitamin D, sulfamethoxazole, and ramifluan reduce the plasma concentration of verapamil by increasing liver metabolism. 3 Cimetidine may increase the bioavailability of verapamil. 4 Verapamil inhibits the elimination of ethanol, leading to increased ethanol concentration in the blood, which may prolong the toxic effects of alcohol. 5 A few cases reported that the combined use of verapamil and aspirin prolonged bleeding time compared with aspirin alone. 6 Combined with beta-blockers
Specifications	40mg
Manufacturer	Shanghai Sine Pharmaceutical Laboratories Co., Ltd.

Verapamil Hydrochloride Tablets
Ingredients	The main ingredient and chemical name of this product are: α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-isopropylphenylacetonitrile hydrochloride
Indication	1 Cytotoxic drugs such as cyclophosphamide, vincristine, procarbazine, prednisone, vinblastine, doxorubicin, and cisplatin reduce the absorption of verapamil. 2 Phenobarbital, hydantoin, vitamin D, sulfamethoxazole, and ramifluan reduce the plasma concentration of verapamil by increasing liver metabolism. 3 Cimetidine may increase the bioavailability of verapamil. 4 Verapamil inhibits the elimination of ethanol, leading to increased ethanol concentration in the blood, which may prolong the toxic effects of alcohol. 5 A few cases reported that the combined use of verapamil and aspirin prolonged bleeding time compared with aspirin alone. 6 Combined with beta-blockers
Specifications	40mg

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Registered Holders

AURORE LIFE SCIENCES PRIVATE LTD

United States
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United States
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United States
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Guide of (+/-)-Verapamil hydrochloride

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Drug Function and Efficacy
Related Drugs
Registered Holders
Recommended Suppliers
Latest News
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