CAS 52-53-9|CAS 152-11-4|Dignover|NU-Verap|Univer|Berkatens|Covera-HS|Dilacoran|Veracim|Verapamil HCl|Verapamil [Usan:Ban:Inn]|Verelan|verapamil|Cardiagutt|Geangin|2-(3,4-dimethoxyphenyl)-5-{[2-(3,4...

General Information

Structure

Molecular Formula

C₂₇H₃₈N₂O₄

Molecular Mass

454.60162

Exact Mass

454.28315771

Charge

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,8,13-16H2,1-7H3

InChIKey

SGTNSNPWRIOYBX-UHFFFAOYSA-N

Canonic Smiles

COc1ccc(cc1OC)CCN(CCCC(c1ccc(c(c1)OC)OC)(C(C)C)C#N)C

Isomeric Smiles

O(c1cc(C(C(C)C)(CCCN(CCc2cc(OC)c(OC)cc2)C)C#N)ccc1OC)C

Calculated Properties

JChem

LogD (pH = 7.4)

3.22

LogD (pH = 5.5)

1.74

Log P

5.04

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

9.23

Polar Surface Area

63.95

Polarizability

51.61

Molar Refractivity

132.65

LOG S

-4.20

Data Source

Names and Identifiers

Brand Name

DignoverNU-VerapUniverBerkatensCovera-HSDilacoranVeracimVerelanCardiaguttGeanginSecuronVeramexIsoptimoCordiloxVasolanCalan SRIsoptin SRNovo-VeramilVeraptinVerexamilDrosteakardIproveratrilQuasarApo-VerapArpamylVerelan PMCalanIsoptinCardibeltin

Synonyms

Verapamil HClVerapamil [Usan:Ban:Inn]Verapamilum [INN-Latin]VerapamilVerapamilo [INN-Spanish]Iproveratril5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-Dimethoxyphenyl)-2-isopropylvaleronitrile(±)-VERAPAMIL HYDROCHLORIDEIsoptinEthimilCoveraVasolanVerelanVerapamilUniverBerkatensVerapressCordiloxGeanginCalanSecuron2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

IUPAC Traditional name

verapamil veraβ 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

IUPAC name

2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

Names and Identifiers

Registration numbers

PubChem CID

2520

CAS Number

52-53-9152-11-4

PubChem SID

46508158160964006223443176

CHEMBL

CHEBI ID

Wikipedia Title

KEGG ID

Chemspider ID

ATC CODE

IUPHAR ligand ID

EC Number

DrugBank ID

Unique Ingredient Identifier

CJ0O37KU29

BKMS React Database

23019919682835098230200239135

BRENDA Database

7.6.2.27.5.2.63.1.1.17.6.2.1

BRENDA Ligand Database

23020023913523019935098196828

BindingDB Database

ACToR Database

CompTox Database

KEGG DRUG Database

SureChEMBL Database

LINCS Database

Registration numbers

Properties

Physical Property

Solubility

4.47 mg/L

Hydrophobicity(logP)

4.7

Melting Point

140-150 °C

Product Information

Certificate of Analysis

Download link

Application(s)

Coronary vasodilator

Used in the treatment of hypertension, angina pectoris, cardiac arrhythmia, and cluster headaches.

Antiarrhythmic (class IV) agent

Smooth muscle relaxant.

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00661

Drug Groups

approved

Description

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

Indication

For the treatment of hypertension, angina, and cluster headache prophylaxis.

Pharmacology

Verapamil is an L-type calcium channel blocker that also has antiarrythmic activity. The R-enantiomer is more effective at reducing blood pressure compared to the S-enantiomer. However, the S-enantiomer is 20 times more potent than the R-enantiomer at prolonging the PR interval in treating arrhythmias.

Toxicity

LD₅₀=8 mg/kg (i.v. in mice)

Affected Organisms

Humans and other mammals

Absorption

90%

Half Life

2.8-7.4 hours

Protein Binding

90%

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.

References

• Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

MP Biomedicals

02195545

Hydrochloride
α₁ -Antagonist and calcium channel modulator.

A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.

Molecule Details

References

PubChem Literature

From Data Sources

• Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. Pubmed

• Atlas, D. and Adler, M., Proc. Nat. Acad. Sci. U.S.A. , 78 : 1237, (1981).

• Guerrero, J.R. et al., Med. Res. Rev., 1984, 4, 87, (rev)

• Carpy, A. et al., Acta Cryst. C, 1985, 41, 624, (cryst struct)

• Chang, Z.L., Anal. Profiles Drug Subst., 1988, 17, 643, (rev)

• Hofer, C.A. et al., Am. J. Med., 1993, 95, 431, (tox)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IRV000; VHA450

• Larangh, J.H., Am. J. Cardiol., Ed., Part 7, 1986, 57, (book)

• Echizen, H. et al., Clin. Pharmacokinet., 1986, 11, 425, (rev)

• Dooley, M. et al., Drugs, 1998, 56, 837-844, (rev)

• Baky, S.H. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 226, (rev, pharmacol)

• Scheid, W. et al., Arzneim.-Forsch., 1991, 41, 901, (tox)

• Longstreth, J.A., Drug Stereochem., (Ed. Wainer, I.W.), M. Dekker, 1993, 315, (rev)

• Bannister, R.M. et al., Org. Process Res. Dev., 2000, 4, 467-472, (synth, pmr)

• Theodore, L.J. et al., J.O.C., 1987, 52, 1309, (synth)

• Knoll, A.G., Angew. Chem., Int. Ed., 1964, 3, 68, (synth, pharmacol)

• Ger. Pat., 1978, 2 631 222; CA, 88, 169796, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 10669; 10670

• Brogden, R.N. et al., Drugs, 1996, 51, 792, (rev)

• Brenna, E. et al., Eur. J. Org. Chem., 2001, 1349-1357, (synth)

• Ramuz, H., Helv. Chim. Acta, 1975, 58, 2050, (synth, ir, ms, pmr, abs config)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 960

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Synonyms

IUPAC Traditional name

verapamil veraβ 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

IUPAC name

2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

Registration numbers

PubChem CID

2520

CAS Number

52-53-9152-11-4

PubChem SID

46508158160964006223443176

CHEMBL

CHEBI ID

Wikipedia Title

KEGG ID

Chemspider ID

ATC CODE

IUPHAR ligand ID

EC Number

DrugBank ID

Unique Ingredient Identifier

CJ0O37KU29

BKMS React Database

23019919682835098230200239135

BRENDA Database

7.6.2.27.5.2.63.1.1.17.6.2.1

BRENDA Ligand Database

23020023913523019935098196828

BindingDB Database

ACToR Database

CompTox Database

KEGG DRUG Database

SureChEMBL Database

LINCS Database

Molecule Details

DB00661

Drug Groups

approved

Description

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

Indication

For the treatment of hypertension, angina, and cluster headache prophylaxis.

Pharmacology

Toxicity

LD₅₀=8 mg/kg (i.v. in mice)

Affected Organisms

Humans and other mammals

Absorption

90%

Half Life

2.8-7.4 hours

Protein Binding

90%

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.

References

• Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

MP Biomedicals

02195545

Hydrochloride
α₁ -Antagonist and calcium channel modulator.

References

PubChem Literature

From Data Sources

• Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. Pubmed

• Atlas, D. and Adler, M., Proc. Nat. Acad. Sci. U.S.A. , 78 : 1237, (1981).

• Guerrero, J.R. et al., Med. Res. Rev., 1984, 4, 87, (rev)

• Carpy, A. et al., Acta Cryst. C, 1985, 41, 624, (cryst struct)

• Chang, Z.L., Anal. Profiles Drug Subst., 1988, 17, 643, (rev)

• Hofer, C.A. et al., Am. J. Med., 1993, 95, 431, (tox)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IRV000; VHA450

• Larangh, J.H., Am. J. Cardiol., Ed., Part 7, 1986, 57, (book)

• Echizen, H. et al., Clin. Pharmacokinet., 1986, 11, 425, (rev)

• Dooley, M. et al., Drugs, 1998, 56, 837-844, (rev)

• Baky, S.H. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 226, (rev, pharmacol)

• Scheid, W. et al., Arzneim.-Forsch., 1991, 41, 901, (tox)

• Longstreth, J.A., Drug Stereochem., (Ed. Wainer, I.W.), M. Dekker, 1993, 315, (rev)

• Bannister, R.M. et al., Org. Process Res. Dev., 2000, 4, 467-472, (synth, pmr)

• Theodore, L.J. et al., J.O.C., 1987, 52, 1309, (synth)

• Knoll, A.G., Angew. Chem., Int. Ed., 1964, 3, 68, (synth, pharmacol)

• Ger. Pat., 1978, 2 631 222; CA, 88, 169796, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 10669; 10670

• Brogden, R.N. et al., Drugs, 1996, 51, 792, (rev)

• Brenna, E. et al., Eur. J. Org. Chem., 2001, 1349-1357, (synth)

• Ramuz, H., Helv. Chim. Acta, 1975, 58, 2050, (synth, ir, ms, pmr, abs config)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 960

Bioactivity

PubChem BioAssay

Properties

Physical Property

Solubility

4.47 mg/L

Hydrophobicity(logP)

4.7

Melting Point

140-150 °C

Product Information

Certificate of Analysis

Download link

Application(s)

Coronary vasodilator

Used in the treatment of hypertension, angina pectoris, cardiac arrhythmia, and cluster headaches.

Antiarrhythmic (class IV) agent

Smooth muscle relaxant.

Molecule

ID:543