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Substance Name: Verapamil hydrochloride [USAN:USP:JAN]
RN: 152-11-4
UNII: V3888OEY5R
InChIKey: DOQPXTMNIUCOSY-UHFFFAOYSA-N

Note

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

Molecular Formula

  • C27-H38-N2-O4.Cl-H

Molecular Weight

  • 491.0681
 

Classification Codes

  • Anti-Anginal
  • Cardiac Depressant (Anti-Arrhythmic)
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Verapamil hydrochloride [USAN:USP:JAN]

Synonyms

  • (+-)-5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile monohydrochloride
  • 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile monohydrochloride
  • Akilen
  • Anpec
  • Apo-Verap
  • Arpamyl LP
  • Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-, monohydrochloride, (+-)-
  • Berkatens
  • Calan
  • Calan SR
  • Calaptin
  • Calaptin 240 SR
  • Calcan hydrochloride
  • Cardiabeltin
  • Cardiagutt
  • Cardibeltin
  • Cardioprotect
  • Caveril
  • Civicor
  • Civicor Retard
  • Coraver
  • Cordilox
  • Cordilox SR
  • Corpamil
  • Covera
  • Covera-HS
  • D-365 hydrochloride
  • Dignover
  • Dilacoran HTA
  • Durasoptin
  • EINECS 205-800-5
  • Elthon
  • Falicard
  • Finoptin
  • Flamon
  • Geangin
  • Harteze
  • Hexasoptin
  • Hexasoptin Retard
  • Hormitol
  • HSDB 3928
  • Ikacor
  • Ikapress
  • Inselon
  • Iproveratril hydrochloride
  • Isoptin
  • Isoptin Retard
  • Isoptin SR
  • Isoptine
  • Isoptino
  • Izoptin
  • Jenapamil
  • Lekoptin
  • Lodixal
  • LU 20175
  • Magotiron
  • Manidon
  • Manidon Retard
  • Novapamyl LP
  • Novo-Veramil
  • NSC 135784
  • NSC 272366
  • Nu-Verap
  • Ormil
  • Praecicor
  • Quasar
  • Rapam
  • Robatelan
  • Securon
  • UNII-V3888OEY5R
  • Univer
  • Univex
  • Vasomil
  • Vasopten
  • Vera-Sanorania
  • Verabeta
  • Veracaps SR
  • Veracor
  • Verahexal
  • Veraloc
  • Veramex
  • Veramil
  • Verapamil Acis
  • Verapamil AL
  • Verapamil Atid
  • Verapamil Basics
  • Verapamil chloridrate
  • Verapamil Ebewe
  • Verapamil HCl
  • Verapamil Henning
  • Verapamil hydrochloride
  • Verapamil Injection
  • Verapamil MSD
  • Verapamil NM
  • Verapamil NM Pharma
  • Verapamil Nordic
  • Verapamil PB
  • Verapamil Riker
  • Verapamil SR
  • Verapamil Verla
  • Verapamil-AbZ
  • Verapin
  • Verapress 240 SR
  • Verasal
  • Verasifar
  • Veratensin
  • Verdilac
  • Verelan
  • Verelan PM
  • Verelan SR
  • Veroptinstada
  • Verpamil
  • Vetrimil
  • Vortac

Systematic Names

  • Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-, monohydrochloride
  • Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-, monohydrochloride
  • Verapamil hydrochloride

Registry Numbers

CAS Registry Number

  • 152-11-4

FDA UNII

  • V3888OEY5R

System Generated Number

  • 0000152114

Molecular Formulas

Molecular Formula

  • C27-H38-N2-O4.Cl-H

Molecular Formula Fragments

  • C27-H38-N2-O4
  • Cl-H
  • COMPONENT

Structure Descriptors

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

InChIKey

DOQPXTMNIUCOSY-UHFFFAOYSA-N

Smiles

CC(C)C(CCCN(C)CCc1ccc(c(c1)OC)OC)(C#N)c2ccc(c(c2)OC)OC.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intramuscular 25mg/kg (25mg/kg)   Drugs in Japan Vol. 6, Pg. 766, 1982.
dog LD50 oral > 400mg/kg (400mg/kg)   Drugs in Japan Vol. 6, Pg. 766, 1982.
guinea pig LD50 oral 140mg/kg (140mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 226, 1981.
infant TDLo intravenous 1026ug/kg (1.026mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE
Archives of Disease in Childhood. Vol. 58, Pg. 465, 1983.
infant TDLo oral 80mg/kg (80mg/kg) CARDIAC: PULSE RATE

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Pediatrics. Vol. 73, Pg. 543, 1984.
man LDLo intravenous 256ug/kg/1H-I (0.256mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Annals of Emergency Medicine. Vol. 14, Pg. 159, 1985.
man LDLo oral 3429ug/kg (3.429mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: NECROTIC GHANGES
Annals of Emergency Medicine. Vol. 22, Pg. 603, 1993.
man LDLo oral 103mg/kg (103mg/kg) BLOOD: OTHER CHANGES

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
American Journal of the Medical Sciences. Vol. 303, Pg. 115, 1992.
man TDLo intravenous 71ug/kg/5M-C (0.071mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: EXCITEMENT
Southern Medical Journal. Vol. 75, Pg. 1429, 1982.
man TDLo oral 143ug/kg/4H-C (0.143mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Intensive Care Medicine. Vol. 8, Pg. 55, 1982.
man TDLo oral 26mg/kg (26mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Human Toxicology. Vol. 4, Pg. 327, 1985.
man TDLo oral 89mg/kg (89mg/kg)   Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 309, 1992.
man TDLo oral 89mg/kg (89mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 309, 1992.
man TDLo oral 68571mg/kg (68571mg/kg) CARDIAC: PULSE RATE

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Medical Journal of Australia. Vol. 155, Pg. 124, 1991.
mouse LD50 intramuscular 45mg/kg (45mg/kg)   Drugs in Japan Vol. -, Pg. 1092, 1990.
mouse LD50 intraperitoneal 41mg/kg (41mg/kg)   Journal of Drug Research. Vol. 16, Pg. 171, 1985.
mouse LD50 intravenous 5795ug/kg (5.795mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 558, 1977.
mouse LD50 oral 163mg/kg (163mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 549, 1962.
mouse LD50 subcutaneous 68mg/kg (68mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 549, 1962.
rat LD50 intramuscular 47mg/kg (47mg/kg)   Drugs in Japan Vol. -, Pg. 1092, 1990.
rat LD50 intraperitoneal 60mg/kg (60mg/kg)   Pharmaceutical Chemistry Journal Vol. 15, Pg. 813, 1981.
rat LD50 intravenous 16mg/kg (16mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 549, 1962.
rat LD50 oral 108mg/kg (108mg/kg)   Drugs in Japan Vol. 6, Pg. 766, 1982.
rat LD50 subcutaneous 107mg/kg (107mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 549, 1962.
women TDLo intravenous 200ug/kg/15S- (0.2mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
New York State Journal of Medicine. Vol. 83, Pg. 1181, 1983.
women TDLo oral 14400ug/kg (14.4mg/kg) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION Annals of Emergency Medicine. Vol. 22, Pg. 196, 1993.
women TDLo oral 58mg/kg (58mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Annals of Emergency Medicine. Vol. 22, Pg. 1229, 1993.
women TDLo oral 72mg/kg/14H-I (72mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE
Annals of Emergency Medicine. Vol. 22, Pg. 1225, 1993.
women TDLo oral 96mg/kg (96mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
American Journal of Emergency Medicine. Vol. 14, Pg. 459, 1996.
women TDLo oral 96mg/kg (96mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Western Journal of Medicine. Vol. 154, Pg. 208, 1991.
women TDLo oral 135mg/kg (135mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: COMA

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
American Journal of Cardiology. Vol. 58, Pg. 1142, 1986.
women TDLo oral 240mg/kg (240mg/kg)   Journal of the American College of Cardiology. Vol. 2, Pg. 1228, 1983.
women TDLo oral 240mg/kg (240mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

ENDOCRINE: HYPERGLYCEMIA
Journal of the American College of Cardiology. Vol. 2, Pg. 1228, 1983.
women TDLo oral 288mg/kg (288mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Acta Anaesthesiologica Scandinavica, Supplementum. Vol. 35(Suppl,