Verapamil Hydrochloride

HCID 62969

Basic information

CAS
152-11-4
Standard SMILES
COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC.Cl
InChIKey
DOQPXTMNIUCOSY-UHFFFAOYSA-N
Molecular formula
C27H39ClN2O4
Average molar mass
491.1 g/mol
Monoisotopic mass
490.2598354

Names & identifiers

Preferred name
Verapamil Hydrochloride
IUPAC
2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile;hydrochloride
English name
(+/-)-Verapamil hydrochloride
Molecular formula
C27H39ClN2O4
Molecular weight
491.06

Names & synonyms

Verapamil hydrochloride152-11-4Verapamil HClVerelanCoveraIsoptin SRVerelan PMCalan SRDTXSID2034095NSC-272366NSC-657799V3888OEY5R
Show more names
manidoncordiloxizoptinhydrochloridelu20175RositolfinoptinHormitolMagotironVerapamil HCId-365hydrochloride
Verapamili hydrochloridumNSC657799LU-20175(+-)-Verapamil hydrochlorideDTXCID0014095NSC272366Securon midManidon sr

Database identifiers

CAS
152-11-4、23313-68-0
PubChem CID
62969
DTXSID
DTXSID2034095
ChEMBL
CHEMBL1280
UNII
V3888OEY5R
EC Number
205-800-5、245-579-2、862-789-5

Properties

Computed structural properties

Topological polar surface area
64 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
13
Heavy atoms
34

Experimental & physicochemical properties

Collision Cross Section208.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
142 °C · 142 °C (dec.)(lit.)
Density
1.0596 · 1.0596 (rough estimate)
refractive index
1.629 · 1.6290 (estimate)
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: >30 mg/mL

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301+H311 (10.4%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal];H301 (99.6%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (15.6%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (77%): Toxic in contact with skin [Danger Acute toxicity, dermal];H315 (18.1%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (18.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H330 (60%): Fatal if inhaled [Danger Acute toxicity, inhalation];H331 (16.7%): Toxic if inhaled [Danger Acute toxicity, inhalation];H335 (18.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H412 (17.8%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 270 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationVerapamil hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information · 1 item

IMAP assessments - Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-, monohydrochloride: Human health tier I assessment;IMAP assessments - Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-, monohydrochloride: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 3 (99.6%);Acute Tox. 3 (77%);Skin Irrit. 2 (18.1%);Eye Irrit. 2 (18.1%);Acute Tox. 2 (60%);Acute Tox. 3 (16.7%);STOT SE 3 (18.9%);Aquatic Chronic 3 (17.8%)

Toxicology

Treatment · 1 item

Treatment of overdosage should be supportive. Beta-adrenergic stimulation or parenteral administration of calcium solutions may increase calcium ion flux across the slow channel and have been used effectively in treatment of deliberate overdosage with verapamil. In a few reported cases, overdose with calcium channel blockers has been associated with hypotension and bradycardia, initially refractory to atropine but becoming more responsive to this treatment when the patients received large doses (close to 1 gram/hour for more than 24 hours) of calcium chloride. Verapamil cannot be removed by hemodialysis. Clinically significant hypotensive reactions or high degree AV block should be treated with vasopressor agents or cardiac pacing, respectively. Asystole should be handled by the usual measures including cardiopulmonary resuscitation. (L1712)

Health Effects · 1 item

Cardiovascular: angina pectoris, AV block (2° & 3°), atrioventricular dissociation, CHF, pulmonary edema, chest pain, claudication, myocardial infarction, palpitations, purpura (vasculitis), syncope. Digestive system: diarrhea, dry mouth, gastrointestinal distress, gingival hyperplasia. Hemic and lymphatic: ecchymosis or bruising. Nervous system: cerebrovascular accident, confusion, equilibrium disorders, insomnia, muscle cramps, psychotic symptoms, shakiness, somnolence, extrapyramidal symptoms. Skin: arthralgia and rash, exanthema, hair loss, hyperkeratosis, macules, sweating, urticaria, Stevens-Johnson syndrome, erythema multiforme. Special senses: blurred vision, tinnitus. Urogenital: gynecomastia, galactorrhea/hyperprolactinemia, increased urination, spotty menstruation, impotence.

Exposure RoutesOrally, 90‰ЫТ100% of Verapamil is absorbed. Intravenous.
Toxicity Summary · 1 item

Verapamil inhibits voltage-dependent calcium channels. Specifically, its effect on L-type calcium channels in the heart causes a reduction in ionotropy and chronotropy, thuis reducing heart rate and blood pressure. Verapamil's mechanism of effect in cluster headache is thought to be linked to its calcium-channel blocker effect, but which channel subtypes are involved is presently not known.

Signs and Symptoms · 1 item

The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries,improved oxygen delivery to the myocardial tissue, and decreased total peripheral resistance, systemic blood pressure, and afterload.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatory information

Regulatory InformationVerapamil hydrochloride: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
8-10
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
YV8320000
ridadr
UN 2811 6.1/PG 3
hs_code
29269090

Chemistry & industry

Pharmacology

Metabolism/MetabolitesRoute of Elimination: Approximately 70% of an administered dose is excreted as metabolites in the urine and 16% or more in the feces within 5 days. About 3% to 4% is excreted in the urine as unchanged drug. Half Life: 2.8-7.4 hours
FDA Pharmacological Classification · 4 items

VERAPAMIL HCI

Calcium Channel Blocker [EPC]; Calcium Channel Antagonists [MoA]; Cytochrome P450 3A Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]

VERAPAMIL HYDROCHLORIDE

Calcium Channel Blocker [EPC]; Calcium Channel Antagonists [MoA]; Cytochrome P450 3A Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]

MeSH Pharmacological Classification · 3 items

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.

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Drugs used to cause dilation of the blood vessels.

Uses & manufacturing

UsesDrug used for the treatment of hypertension, angina, and cluster headache prophylaxis.
Applications · 5 items

DescriptionVerapamil 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

Uses±)-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.

Usesanalgesic, antipyretic

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

General DescriptionPharmaceutical 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.

Upstream & downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Related reactions

5 records

Compound notes

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