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Substance Name: Verapamil [USAN:INN:BAN]
RN: 52-53-9
UNII: CJ0O37KU29
InChIKey: SGTNSNPWRIOYBX-UHFFFAOYSA-N
Note
- A calcium channel blocker that is a class IV anti-arrhythmia agent.
Molecular Formula
- C27-H38-N2-O4
Molecular Weight
- 454.607
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anti-Arrhythmia Agents
- Antiviral (COVID-19)
- Calcium Channel Blockers
- Calcium-Regulating Hormones and Agents
- Cardiovascular Agents
- Drug / Therapeutic Agent
- Human Data
- Membrane Transport Modulators
- Reproductive Effect
- Vasodilator (Coronary)
- Vasodilator Agents
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Names and Synonyms
Name of Substance
- Verapamil
- Verapamil [USAN:INN:BAN]
MeSH Heading
- Verapamil
Synonyms
- 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
- alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
- alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)-methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile
- alpha-Isopropyl-alpha-((N-methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
- Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino) propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
- Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
- CCRIS 6749
- CP 16533-1
- CP-16,533-1
- CP-16533-1
- D 365
- D-365
- Dexverapamil
- Dilacoran
- dl-Verapamil
- EINECS 200-145-1
- EINECS 260-462-6
- Falicard
- Finoptin
- HSDB 3928
- Iproveratril
- Isoptimo
- Isoptine
- Lekoptin
- NSC 272306NA
- R,S-Verapamil
- UNII-CJ0O37KU29
- Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
- Vasolan
- Verapamil
- Verapamilo
- Verapamilo [INN-Spanish]
- Verapamilum
- Verapamilum [INN-Latin]
Systematic Names
- Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
- Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
- Verapamil
Registry Numbers
CAS Registry Number
- 52-53-9
FDA UNII
- CJ0O37KU29
Other Registry Numbers
- 1007128-78-0
- 56949-77-0
- 7482-85-1
System Generated Number
- 0000052539
Structure Descriptors
InChI
InChI=1S/C27H38N2O4/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,8,13-16H2,1-7H3InChIKey
SGTNSNPWRIOYBX-UHFFFAOYSA-NSmiles
COc1ccc(CCN(C)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | intravenous | 250ug/kg/5M-C (0.25mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | American Heart Journal. Vol. 106, Pg. 145, 1983. |
man | LDLo | oral | 83mg/kg (83mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | American Journal of Emergency Medicine. Vol. 7, Pg. 624, 1989. |
man | LDLo | oral | 2gm/kg (2000mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION CARDIAC: OTHER CHANGES | Chest. Vol. 75, Pg. 200, 1979. |
man | TDLo | intravenous | 71ug/kg (0.071mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: DYSPNEA | American Heart Journal. Vol. 111, Pg. 622, 1986. |
man | TDLo | intravenous | 1429ug/kg/5M- (1.429mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS CARDIAC: PULSE RATE SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | New England Journal of Medicine. Vol. 306, Pg. 238, 1982. |
man | TDLo | oral | 3429ug/kg (3.429mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: PULSE RATE LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | Critical Care Medicine. Vol. 19, Pg. 436, 1991. |
man | TDLo | oral | 42857ug/kg (42.857mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | European Heart Journal. Vol. 2, Pg. 239, 1981. |
man | TDLo | oral | 46mg/kg (46mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Clinical Toxicology. Vol. 17, Pg. 395, 1980. |
man | TDLo | oral | 48mg/kg/2W-I (48mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" | New England Journal of Medicine. Vol. 306, Pg. 612, 1982. |
mouse | LD50 | intraperitoneal | 43mg/kg (43mg/kg) | Journal of Drug Research. Vol. 15(1-2), Pg. 121, 1984. | |
mouse | LD50 | intravenous | 1520ug/kg (1.52mg/kg) | European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 188, 1975. | |
mouse | LD50 | oral | 130mg/kg (130mg/kg) | Farmakologiya i Toksikologiya Vol. 54(2), Pg. 40, 1991. | |
mouse | LD50 | subcutaneous | 30770ug/kg (30.77mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 34, Pg. 329, 1982. | |
rat | LD50 | intravenous | 7250ug/kg (7.25mg/kg) | Pharmaceutical Chemistry Journal Vol. 22, Pg. 123, 1988. | |
rat | LD50 | oral | 163mg/kg (163mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 25, Pg. 351, 1990. | |
women | LDLo | oral | 1364ug/kg (1.364mg/kg) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA CARDIAC: OTHER CHANGES LIVER: FATTY LIVER DEGERATION | Archives of Toxicology. Vol. 37, Pg. 89, 1977. |
women | LDLo | oral | 192mg/kg (192mg/kg) | BEHAVIORAL: COMA CARDIAC: PULSE RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Netherlands Journal of Medicine. Vol. 26, Pg. 130, 1983. |
women | LDLo | oral | 300mg/kg (300mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE CARDIAC: PULSE RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Medical Journal of Australia. Vol. 158, Pg. 202, 1993. |
women | TDLo | oral | 48mg/kg (48mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Clinical Cardiology. Vol. 5, Pg. 219, 1982. |
women | TDLo | oral | 64mg/kg (64mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: CHANGE IN RATE CARDIAC: PULSE RATE | British Medical Journal. Vol. 2, Pg. 1127, 1978. |
women | TDLo | oral | 80mg/kg (80mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION BEHAVIORAL: COMA CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP | Human & Experimental Toxicology. Vol. 16, Pg. 35, 1997. |
women | TDLo | oral | 128mg/kg (128mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) BEHAVIORAL: GENERAL ANESTHETIC KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | International Journal of Cardiology. Vol. 1, Pg. 101, 1981. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | < 25 | deg C | EXP | |
pKa Dissociation Constant | 8.92 | (none) | EXP | |
log P (octanol-water) | 3.79 | (none) | EXP | |
Water Solubility | 4.470 | mg/L | 25 | EST |
Vapor Pressure | 2.79E-11 | mm Hg | 25 | EST |
Henry's Law Constant | 8.79E-15 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.86E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.