Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-02-16 09:20:18 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001850
Secondary Accession Numbers
  • HMDB0014799
  • HMDB01850
  • HMDB14799
Metabolite Identification
Common NameVerapamil
DescriptionVerapamil is only found in individuals that have used or taken this drug. Verapamil is a calcium channel blocker that is a class IV anti-arrhythmia agent. [PubChem]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. [PubChem] Calcium channel antagonists can be quite toxic. In the management of poisoning, early recognition is critical. Calcium channel antagonists are frequently prescribed, and the potential for serious morbidity and mortality with over dosage is significant. Ingestion of these agents should be suspected in any patient who presents in an overdose situation with unexplained hypotension and conduction abnormalities. The potential for toxicity should be noted in patients with underlying hepatic or renal dysfunction who are receiving therapeutic doses. (PMID 8213877 ).
Structure
Data?1582752212
Synonyms
ValueSource
CP-165331VerapamilHMDB
Covera-HSHMDB
VerelanHMDB
IsoptinHMDB
D-365IproveratrilHMDB
CP-16533-1CalanHMDB
TarkaHMDB
AkilenHMDB
AnpecHMDB
Apo-verapHMDB
Arpamyl LPHMDB
BerkatensHMDB
CalanHMDB
Calan SRHMDB
CalaptinHMDB
Calaptin 240 SRHMDB
CalcanHMDB
CardiabeltinHMDB
CardiaguttHMDB
CardibeltinHMDB
CardioprotectHMDB
CaverilHMDB
CivicorHMDB
Civicor retardHMDB
CoraverHMDB
CordiloxHMDB
Cordilox SRHMDB
CorpamilHMDB
D-365HMDB
delta-365HMDB
DignoverHMDB
DilacoranHMDB
Dilacoran htaHMDB
DurasoptinHMDB
ElthonHMDB
FalicardHMDB
FinoptinHMDB
FlamonHMDB
GeanginHMDB
HartezeHMDB
HexasoptinHMDB
Hexasoptin retardHMDB
HormitolHMDB
IkacorHMDB
IkapressHMDB
InselonHMDB
IproveratrilHMDB
Isoptin retardHMDB
Isoptin SRHMDB
IsoptineHMDB
IsoptinoHMDB
IsotopinHMDB
IzoptinHMDB
JenapamilHMDB
LekoptinHMDB
LodixalHMDB
MagotironHMDB
ManidonHMDB
Manidon retardHMDB
Novapamyl LPHMDB
Novo-veramilHMDB
Nu-verapHMDB
OrmilHMDB
PraecicorHMDB
QuasarHMDB
RapamHMDB
RobatelanHMDB
SecuronHMDB
UniverHMDB
UnivexHMDB
VasolanHMDB
VasomilHMDB
VasoptenHMDB
Vera-sanoraniaHMDB
VerabetaHMDB
Veracaps SRHMDB
VeracorHMDB
VerahexalHMDB
VeralocHMDB
VeramexHMDB
VeramilHMDB
Verapamil acisHMDB
Verapamil alHMDB
Verapamil atidHMDB
Verapamil basicsHMDB
Verapamil ebeweHMDB
Verapamil HCLHMDB
Verapamil henningHMDB
Verapamil injectionHMDB
Verapamil MSDHMDB
Verapamil NMHMDB
Verapamil NM pharmaHMDB
Verapamil nordicHMDB
Verapamil PBHMDB
Verapamil rikerHMDB
Verapamil SRHMDB
Verapamil verlaHMDB
Verapamil-abzHMDB
VerapamiloHMDB
VerapamilumHMDB
VerapinHMDB
Verapress 240 SRHMDB
VerasalHMDB
VerasifarHMDB
VeratensinHMDB
VerdilacHMDB
Verelan PMHMDB
Verelan SRHMDB
VeroptinstadaHMDB
VerpamilHMDB
VetrimilHMDB
VortacHMDB
DexverapamilHMDB
Hydrochloride, verapamilHMDB
Sandoz brand OF verapamilHMDB
Verapamil hydrochlorideHMDB
Verapamil sandoz brandHMDB
Chemical FormulaC27H38N2O4
Average Molecular Weight454.6016
Monoisotopic Molecular Weight454.283157714
IUPAC Name2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
Traditional Nameveraβ
CAS Registry Number52-53-9
SMILES
COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1
InChI Identifier
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
InChI KeySGTNSNPWRIOYBX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Phenethylamine
  • Phenylpropane
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Alkyl aryl ether
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Nitrile
  • Carbonitrile
  • Ether
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CPhysProp
Boiling Point243-246 °C at 1.00E-02 mm HgPhysProp
Water Solubility4.47 mg/LNot Available
LogP3.79HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM210.230932474
[M+H]+McLean208.7430932474
[M+H]+Not Available208.913http://allccs.zhulab.cn/database/detail?ID=AllCCS00000772
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP5.23ALOGPS
logP5.04ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.95 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity132.65 m³·mol⁻¹ChemAxon
Polarizability51.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.34531661259
DarkChem[M-H]-206.74831661259
AllCCS[M+H]+214.79332859911
AllCCS[M-H]-215.59332859911
DeepCCS[M+H]+214.88830932474
DeepCCS[M-H]-212.5330932474
DeepCCS[M-2H]-245.7830932474
DeepCCS[M+Na]+221.00830932474
AllCCS[M+H]+214.832859911
AllCCS[M+H-H2O]+212.732859911
AllCCS[M+NH4]+216.732859911
AllCCS[M+Na]+217.332859911
AllCCS[M-H]-215.632859911
AllCCS[M+Na-2H]-217.232859911
AllCCS[M+HCOO]-219.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VerapamilCOC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C13582.1Standard polar33892256
VerapamilCOC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C13106.0Standard non polar33892256
VerapamilCOC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C13165.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cdu-4391500000-cd36ebd65bc8c77659612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-3519000000-b5e0b9e0caac5cb572222014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil 10V, Negative-QTOFsplash10-014r-3372900000-cd7073ee75752c627c392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil 40V, Negative-QTOFsplash10-0a4r-5976300000-921d7eee522825f0dfde2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil 20V, Negative-QTOFsplash10-0uk9-3594400000-225aaa8c832d0eb167e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004l-0702900000-6a46ea2d5eed6d8b01eb2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-4109800000-80d342090a0be3344e822012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-054w-0954400000-2def387c7c93ab2114232012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0a4i-0000900000-4cde9a4b3a4f83d16afc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0a4i-0000900000-980b47834e505d54a0e62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-066r-0902800000-ae024239c46b339174262012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-014i-0901000000-81d1159b3102cff762182012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-0900000000-d9c344fee7b45b4030e62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0gb9-0914000000-070bdb975910e9aae99c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-03di-0390000000-f41d80462c5d06c4f0012012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0097-2980000000-9a2ab0bcab33f7eaac6b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0uxr-0900000000-252a9989a8511cb2db802012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0f79-0900000000-4fd6ca2c6c19c3bbf8f02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0000900000-4365a47b2dc2f86bb2722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0000900000-e6a2b357160bf5b92c222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOFsplash10-066r-0902400000-d8eac2ccd0a767c7e4322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOFsplash10-014i-0901000000-688f3c2345c5d9ccb8a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-cd09f8a2be876936f6622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0918000000-76641dd6dbc5cb05e79a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0000900000-05ea95eb1f39b65152122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-ITFT , positive-QTOFsplash10-066r-0902600000-a675e624692c25472ce82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Verapamil LC-ESI-ITFT , positive-QTOFsplash10-014i-0901000000-70d820628d26135572392017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00661 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00661 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00661
Phenol Explorer Compound IDNot Available
FooDB IDFDB022708
KNApSAcK IDNot Available
Chemspider ID2425
KEGG Compound IDC07188
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVerapamil
METLIN ID3009
PubChem Compound2520
PDB IDNot Available
ChEBI ID77733
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Takeda H, Yamazaki Y, Akahane M, Igawa Y, Ajisawa Y, Nishizawa O: Role of the beta(3)-adrenoceptor in urine storage in the rat: comparison between the selective beta(3)-adrenoceptor agonist, CL316, 243, and various smooth muscle relaxants. J Pharmacol Exp Ther. 2000 Jun;293(3):939-45. [PubMed:10869395 ]
  2. Wang YH, Jones DR, Hall SD: Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71. Epub 2005 Feb 2. [PubMed:15689501 ]
  3. Byerly WG, Hartmann A, Foster DE, Tannenbaum AK: Verapamil in the treatment of maternal paroxysmal supraventricular tachycardia. Ann Emerg Med. 1991 May;20(5):552-4. [PubMed:2024796 ]
  4. Miller MR, Withers R, Bhamra R, Holt DW: Verapamil and breast-feeding. Eur J Clin Pharmacol. 1986;30(1):125-6. [PubMed:3709626 ]
  5. Takano A, Kusuhara H, Suhara T, Ieiri I, Morimoto T, Lee YJ, Maeda J, Ikoma Y, Ito H, Suzuki K, Sugiyama Y: Evaluation of in vivo P-glycoprotein function at the blood-brain barrier among MDR1 gene polymorphisms by using 11C-verapamil. J Nucl Med. 2006 Sep;47(9):1427-33. [PubMed:16954549 ]
  6. Fakih H, MacLusky N, DeCherney A, Wallimann T, Huszar G: Enhancement of human sperm motility and velocity in vitro: effects of calcium and creatine phosphate. Fertil Steril. 1986 Nov;46(5):938-44. [PubMed:3781011 ]
  7. Suzuki S, Nishimaki-Mogami T, Tamehiro N, Inoue K, Arakawa R, Abe-Dohmae S, Tanaka AR, Ueda K, Yokoyama S: Verapamil increases the apolipoprotein-mediated release of cellular cholesterol by induction of ABCA1 expression via Liver X receptor-independent mechanism. Arterioscler Thromb Vasc Biol. 2004 Mar;24(3):519-25. Epub 2004 Jan 15. [PubMed:14726413 ]
  8. Glusa E: Effect of verapamil on platelet aggregation. Folia Haematol Int Mag Klin Morphol Blutforsch. 1988;115(4):469-73. [PubMed:2465955 ]
  9. Ceccato A, Chiap P, Hubert P, Toussaint B, Crommen J: Automated determination of verapamil and norverapamil in human plasma with on-line coupling of dialysis to high-performance liquid chromatography and fluorometric detection. J Chromatogr A. 1996 Oct 25;750(1-2):351-60. [PubMed:8938391 ]
  10. Nanni G, Panocchia N, Tacchino R, Foco M, Piccioni E, Castagneto M: Increased incidence of infection in verapamil-treated kidney transplant recipients. Transplant Proc. 2000 May;32(3):551-3. [PubMed:10812109 ]
  11. Affolter H, Burkard WP, Pletscher A: Verapamil, an antagonist at 5-hydroxytryptamine receptors of human blood platelets. Eur J Pharmacol. 1985 Jan 22;108(2):157-62. [PubMed:3156755 ]
  12. Rumiantsev DO, Piotrovskii VK, Riabokon' OS, Metelitsa VI: [Comparison of the verapamil concentration of human blood serum and saliva]. Farmakol Toksikol. 1987 Jan-Feb;50(1):85-9. [PubMed:3556560 ]
  13. Gramatte T, Oertel R: Intestinal secretion of intravenous talinolol is inhibited by luminal R-verapamil. Clin Pharmacol Ther. 1999 Sep;66(3):239-45. [PubMed:10511059 ]
  14. Hsiao P, Sasongko L, Link JM, Mankoff DA, Muzi M, Collier AC, Unadkat JD: Verapamil P-glycoprotein transport across the rat blood-brain barrier: cyclosporine, a concentration inhibition analysis, and comparison with human data. J Pharmacol Exp Ther. 2006 May;317(2):704-10. Epub 2006 Jan 13. [PubMed:16415090 ]
  15. von Richter O, Greiner B, Fromm MF, Fraser R, Omari T, Barclay ML, Dent J, Somogyi AA, Eichelbaum M: Determination of in vivo absorption, metabolism, and transport of drugs by the human intestinal wall and liver with a novel perfusion technique. Clin Pharmacol Ther. 2001 Sep;70(3):217-27. [PubMed:11557909 ]
  16. Narang PK, Blumhardt CL, Doran AR, Pickar D: Steady-state cerebrospinal fluid transfer of verapamil and metabolites in patients with schizophrenia. Clin Pharmacol Ther. 1988 Nov;44(5):550-7. [PubMed:3180637 ]
  17. Szymanski W, Skublicki S, Jankowski A, Kotzbach R: [Pharmacokinetic investigations of verapamil used as a concomitant drug in treatment of premature labor]. Ginekol Pol. 1992 Apr;63(4):166-71. [PubMed:1303922 ]
  18. Wang YH, Jones DR, Hall SD: Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66. [PubMed:14744949 ]
  19. Dumestre-Toulet V, Cirimele V, Gromb S, Belooussoff T, Lavault D, Ludes B, Kintz P: Last performance with VIAGRA: post-mortem identification of sildenafil and its metabolites in biological specimens including hair sample. Forensic Sci Int. 2002 Mar 28;126(1):71-6. [PubMed:11955836 ]
  20. Bauer LA, Horn JR, Maxon MS, Easterling TR, Shen DD, Strandness DE Jr: Effect of metoprolol and verapamil administered separately and concurrently after single doses on liver blood flow and drug disposition. J Clin Pharmacol. 2000 May;40(5):533-43. [PubMed:10806607 ]
  21. Hofer CA, Smith JK, Tenholder MF: Verapamil intoxication: a literature review of overdoses and discussion of therapeutic options. Am J Med. 1993 Oct;95(4):431-8. [PubMed:8213877 ]
  22. Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. [PubMed:8725386 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1D gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA)
Gene Name:
CACNA1D
Uniprot ID:
Q01668
Molecular weight:
245138.8
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
General function:
Involved in ion channel activity
Specific function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular weight:
126653.5
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1C gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1C subunit play an important role in excitation-contraction coupling in the heart. The various isoforms display marked differences in the sensitivity to DHP compounds. Binding of calmodulin or CABP1 at the same regulatory sites results in an opposit effects on the channel function
Gene Name:
CACNA1C
Uniprot ID:
Q13936
Molecular weight:
248974.1
General function:
Involved in inward rectifier potassium channel activity
Specific function:
This receptor is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by extracellular barium
Gene Name:
KCNJ11
Uniprot ID:
Q14654
Molecular weight:
43540.4
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1F gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA)
Gene Name:
CACNA1F
Uniprot ID:
O60840
Molecular weight:
220675.9
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1G gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by mibefradil. A particularity of this type of channels is an opening at quite negative potentials and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes
Gene Name:
CACNA1G
Uniprot ID:
O43497
Molecular weight:
262468.6
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. Isoform alpha-1I gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by nickel and mibefradil. A particularity of this type of channels is an opening at quite negative potentials, and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes. Gates in voltage ranges similar to, but higher than alpha 1G or alpha 1H
Gene Name:
CACNA1I
Uniprot ID:
Q9P0X4
Molecular weight:
245100.8

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1

Only showing the first 10 proteins. There are 18 proteins in total.