Identification

Name
Verapamil
Accession Number
DB00661  (APRD00335)
Type
Small Molecule
Groups
Approved
Description

Verapamil is a phenylalkylamine calcium channel blocker used in the treatment of high blood pressure, heart arrhythmias, and angina,16 and was the first calcium channel antagonist to be introduced into therapy in the early 1960s.13 It is a member of the non-dihydropyridine class of calcium channel blockers, which includes drugs like diltiazem and flunarizine, but is chemically unrelated to other cardioactive medications.16 Verapamil is administered as a racemic mixture containing equal amounts of the S- and R-enantiomer, each of which is pharmacologically distinct - the S-enantiomer carries approximately 20-fold greater potency than the R-enantiomer, but is metabolized at a higher rate.5

Structure
Thumb
Synonyms
  • Iproveratril
  • Verapamil
  • Vérapamil
  • Verapamilo
  • Verapamilum
External IDs
CP-16,533-1 / D-365
Product Ingredients
IngredientUNIICASInChI Key
Verapamil hydrochlorideV3888OEY5R152-11-4DOQPXTMNIUCOSY-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CalanTablet, film coated120 mg/1OralG.D. Searle LLC Division of Pfizer Inc1984-09-10Not applicableUs
CalanTablet, film coated40 mg/1OralG.D. Searle LLC2006-06-012006-06-01Us
CalanTablet, film coated80 mg/1OralG.D. Searle LLC Division of Pfizer Inc1984-09-102018-06-30Us
CalanTablet, film coated120 mg/1OralPhysicians Total Care, Inc.1994-07-052012-06-30Us
Calan SRTablet, film coated, extended release240 mg/1OralG.D. Searle LLC Division of Pfizer Inc1986-12-16Not applicableUs00025 1891 51 nlmimage10 4d132699
Calan SRTablet, film coated, extended release180 mg/1OralG.D. Searle LLC Division of Pfizer Inc1989-12-15Not applicableUs
Calan SRTablet, film coated, extended release120 mg/1OralG.D. Searle LLC Division of Pfizer Inc1991-03-06Not applicableUs
Calan SRTablet, film coated, extended release180 mg/1OralPhysicians Total Care, Inc.1992-11-172012-06-30Us
Calan SRTablet, film coated, extended release120 mg/1OralPhysicians Total Care, Inc.1994-07-252012-06-30Us
Covera-HSTablet, extended release240 mgOralPfizer Canada Ulc1997-11-132013-02-15Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-verapamil - 120mgTabletOralAltimed Pharma Inc.1990-12-312004-08-03Canada
Alti-verapamil - 80mgTabletOralAltimed Pharma Inc.1990-12-312004-08-03Canada
Apo-verap SRTablet, extended releaseOralApotex Corporation2003-04-24Not applicableCanada
Apo-verap SRTablet, extended releaseOralApotex Corporation2003-04-24Not applicableCanada
Apo-verap SRTablet, extended releaseOralApotex Corporation2003-04-24Not applicableCanada
Apo-verap Tab 80mgTabletOralApotex Corporation1989-12-31Not applicableCanada
Apo-verap Tablet 120mgTabletOralApotex Corporation1989-12-31Not applicableCanada
Dom-verapamil SR 240mg TabletsTablet, extended releaseOralDominion Pharmacal1999-12-16Not applicableCanada
Med Verapamil TabletsTabletOralMedican Pharma Incorporated1999-03-082011-03-29Canada
Med Verapamil TabletsTabletOralMedican Pharma Incorporated1999-03-082011-03-29Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
TarkaVerapamil hydrochloride (240 mg/1) + Trandolapril (4 mg/1)Tablet, film coated, extended releaseOralPhysicians Total Care, Inc.2009-06-25Not applicableUs00074 3290 13 nlmimage10 ec1d766b
TarkaVerapamil hydrochloride (240 mg) + Trandolapril (4 mg)Tablet, extended releaseOralBgp Pharma Ulc2002-07-152019-11-19Canada
TarkaVerapamil hydrochloride (240 mg/1) + Trandolapril (2 mg/1)Tablet, film coated, extended releaseOralPhysicians Total Care, Inc.2005-05-27Not applicableUs
TarkaVerapamil hydrochloride (180 mg/1) + Trandolapril (2 mg/1)Tablet, film coated, extended releaseOralPhysicians Total Care, Inc.2009-01-01Not applicableUs
TarkaVerapamil hydrochloride (180 mg/1) + Trandolapril (2 mg/1)Tablet, film coated, extended releaseOralAbbVie Inc.1996-10-222021-08-14Us
TarkaVerapamil hydrochloride (240 mg) + Trandolapril (2 mg)Tablet, extended releaseOralBgp Pharma Ulc2002-07-152019-11-19Canada
TarkaVerapamil hydrochloride (240 mg/1) + Trandolapril (4 mg/1)Tablet, film coated, extended releaseOralAbbVie Inc.1996-10-222021-08-18Us0074 329020180814 13942 gpsp61
TarkaVerapamil hydrochloride (240 mg) + Trandolapril (1 mg)Tablet, extended releaseOralAbbott2002-07-152010-11-12Canada
TarkaVerapamil hydrochloride (240 mg/1) + Trandolapril (2 mg/1)Tablet, film coated, extended releaseOralAbbVie Inc.1996-10-222021-09-13Us
TarkaVerapamil hydrochloride (180 mg) + Trandolapril (2 mg)Tablet, extended releaseOralAbbott2002-07-152010-11-12Canada
International/Other Brands
Bosoptin (Bosnalijek) / Isoptin (Abbott) / Verisop (Gerard) / Vermin (Ratiopharm) / Vermine (Pharmasant) / Verogalid (Ivax) / Verogalid ER (Ivax) / Verpamil (Mylan) / Vertab (Trinity-Chiesi) / Vetrimil (CCPC) / Zolvera (Rosemont)
Categories
UNII
CJ0O37KU29
CAS number
52-53-9
Weight
Average: 454.6016
Monoisotopic: 454.283157714
Chemical Formula
C27H38N2O4
InChI Key
SGTNSNPWRIOYBX-UHFFFAOYSA-N
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
IUPAC Name
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
SMILES
COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

Pharmacology

Indication

Verapamil is indicated in the treatment of vasopastic (i.e. Prinzmetal's) angina, unstable angina, and chronic stable angina. It is also indicated to treat hypertension, for the prophylaxis of repetitive paroxysmal supraventricular tachycardia, and in combination with digoxin to control ventricular rate in patients with atrial fibrillation or atrial flutter.16 Given intravenously, it is indicated for the treatment of various supraventricular tachyarrhythmias, including rapid conversion to sinus rhythm in patients with supraventricular tachycardia and for temporary control of ventricular rate in patients with atrial fibrillation or atrial flutter.15

Verapamil is commonly used off-label for prophylaxis of cluster headaches.4

Associated Conditions
Pharmacodynamics

Verapamil is an L-type calcium channel blocker with antiarrhythmic, antianginal, and antihypertensive activity.16 Immediate-release verapamil has a relatively short duration of action, requiring dosing 3 to 4 times daily,16 but extended-release formulations are available that allow for once-daily dosing.14,19 As verapamil is a negative inotropic medication (i.e. it decreases the strength of myocardial contraction), it should not be used in patients with severe left ventricular dysfunction or hypertrophic cardiomyopathy as the decrease in contractility caused by verapamil may increase the risk of exacerbating these pre-existing conditions.14

Mechanism of action

Verapamil inhibits L-type calcium channels by binding to a specific area of their alpha-1 subunit14 - Cav1.2, the predominant L-type calcium channel in the cardiovascular system, is found in vascular smooth muscle and myocardial tissue and is responsible for control of peripheral vascular resistance and heart contractility.10 Calcium influx through these channels allows for the propagation of action potentials necessary for the contraction of muscle tissue and the heart's electrical pacemaker activity. Verapamil binds to these channels in a voltage- and frequency-dependent manner, meaning affinity is increased 1) as vascular smooth muscle membrane potential is reduced, and 2) with excessive depolarizing stimulus.14

Verapamil's mechanism of action in the treatment of angina and hypertension is largely the same. Inhibition of calcium influx prevents the contraction of vascular smooth muscle, causing relaxation/dilation of blood vessels throughout the peripheral circulation - this lowers systemic vascular resistance (i.e. afterload) and thus blood pressure. This reduction in vascular resistance also reduces the force against which the heart must push, decreasing myocardial energy consumption and oxygen requirements and thus alleviating angina.16

Electrical activity through the AV node is responsible for determining heart rate, and this activity is dependent upon calcium influx through L-type calcium channels. By inhibiting these channels and decreasing the influx of calcium, verapamil prolongs the refractory period of the AV node and slows conduction, thereby slowing and controlling the heart rate in patients with arrhythmia.16

Verapamil's mechanism of action in the treatment of cluster headaches is unclear, but is thought to result from an effect on other calcium channels (e.g. N-, P-, Q-, or T-type).4

Verapamil is known to interact with other targets, including other calcium channels,7,8 potassium channels,6,4 and adrenergic receptors.11,12

TargetActionsOrganism
AVoltage-dependent L-type calcium channel subunit alpha-1C
inhibitor
Humans
UVoltage-dependent N-type calcium channel subunit alpha-1B
inhibitor
Humans
UVoltage-dependent P/Q-type calcium channel subunit alpha-1A
inhibitor
Humans
UATP-sensitive inward rectifier potassium channel 11
inhibitor
Humans
UVoltage-dependent T-type calcium channel subunit alpha-1G
inhibitor
Humans
UVoltage-dependent T-type calcium channel subunit alpha-1H
inhibitor
Humans
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
USodium-dependent serotonin transporter
unknown
Humans
UAlpha-1A adrenergic receptor
antagonist
Humans
UAlpha-1B adrenergic receptor
antagonist
Humans
UAlpha-1D adrenergic receptor
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

More than 90% of orally administered verapamil is absorbed - despite this, bioavailability ranges only from 20% to 30% due to rapid biotransformation following first-pass metabolism in the portal circulation.16 Absorption kinetic parameters are largely dependent on the specific formulation of verapamil involved. Immediate-release verapamil reaches peak plasma concentrations (i.e. Tmax) between 1-2 hours following administration,16 whereas sustained-release formulations tend to have a Tmax between 6 - 11 hours.14,19

AUC and Cmax values are similarly dependent upon formulation. Chronic administration of immediate-release verapamil every 6 hours resulted in plasma concentrations between 125 and 400 ng/mL.16 Steady-state AUC0-24h and Cmax values for a sustained-release formulation were 1037 ng∙h/ml and 77.8 ng/mL for the R-isomer and 195 ng∙h/ml and 16.8 ng/mL for the S-isomer, respectively.14

Interestingly, the absorption kinetics of verapamil are highly stereospecific - following oral administration of immediate-release verapamil every 8 hours, the relative systemic availability of the S-enantiomer compared to the R-enantiomer was 13% after a single dose and 18% at steady-state.14

Volume of distribution

Verapamil has a steady-state volume of distribution of approximately 300L for its R-enantiomer and 500L for its S-enantiomer.4

Protein binding

Verapamil is extensively protein-bound in plasma. R-verapamil is 94% bound to serum albumin while S-verapamil is 88% bound. Additionally, R-verapamil is 92% bound to alpha-1 acid glycoprotein and S-verapamil is 86% bound.16

Metabolism

Verapamil is extensively metabolized by the liver, with up to 80% of an administered dose subject to elimination via pre-systemic metabolism - interestingly, this first-pass metabolism appears to clear the S-enantiomer of verapamil much faster than the R-enantiomer.14,9 The remaining parent drug undergoes O-demethylation, N-dealkylation, and N-demethylation to a number of different metabolites via the cytochrome P450 enzyme system.9 Norverapamil, one of the major circulating metabolites, is the result of verapamil's N-demethylation via CYP2C8, CYP3A4, and CYP3A5,9 and carries approximately 20% of the cardiovascular activity of its parent drug.14 The other major pathway involved in verapamil metabolism is N-dealkylation via CYP2C8, CYP3A4, and CYP1A2 to the D-617 metabolite. Both norverapamil and D-617 are further metabolized by other CYP isoenzymes to various secondary metabolites. CYP2D6 and CYP2E1 have also been implicated in the metabolic pathway of verapamil, albeit to a minor extent.9 Minor pathways of verapamil metabolism involve its O-demethylation to D-703 via CYP2C8, CYP2C9, and CYP2C18, and to D-702 via CYP2C9 and CYP2C18.9

Several steps in verapamil's metabolic pathway show stereoselective preference for the S-enantiomer of the given substrate, including the generation of the D-620 metabolite by CYP3A4/5 and the D-617 metabolite by CYP2C8.9

Route of elimination

Approximately 70% of an administered dose is excreted as metabolites in the urine and ≥16% in the feces within 5 days. Approximately 3% - 4% is excreted in the urine as unchanged drug.16

Half life

Single-dose studies of immediate-release verapamil have demonstrated an elimination half-life of 2.8 to 7.4 hours, which increases to 4.5 to 12.0 hours following repetitive dosing.16 The elimination half-life is also prolonged in patients with hepatic insufficiency (14 to 16 hours) and in the elderly (approximately 20 hours).14 Intravenously administered verapamil has rapid distribution phase half-life of approximately 4 minutes, followed by a terminal elimination phase half-life of 2 to 5 hours.15

Clearance

Systemic clearance following 3 weeks of continuous treatment was approximately 340 mL/min for R-verapamil and 664 mL/min for S-verapamil.5 Of note, apparent oral clearance appears to vary significantly between single dose and multiple-dose conditions. The apparent oral clearance following single doses of verapamil was approximately 1007 mL/min for R-verapamil and 5481 mL/min for S-verapamil, whereas 3 weeks of continuous treatment resulted in apparent oral clearance values of approximately 651 mL/min for R-verapamil and 2855 mL/min for S-verapamil.5

Toxicity

Verapamil's reported oral TDLo is 14.4 mg/kg in women and 3.429 mg/kg in men.18 The oral LD50 is 150 mg/kg in rats and 163 mg/kg in mice.18

As there is no antidote for verapamil overdosage, treatment is largely supportive. Symptoms of overdose are generally consistent with verapamil's adverse effect profile (i.e. hypotension, bradycardia, arrhythmia) but instances of non-cardiogenic pulmonary edema have been observed following ingestion of large overdoses (up to 9 grams).14 In acute overdosage, consider the use of gastrointestinal decontamination with cathartics and/or bowel irrigation. Patients presenting with significant myocardial depression may require intravenous calcium, atropine, vasopressors, or other inotropes. Consider the formulation responsible for the overdose prior to treatment - sustained-release formulations may result in delayed pharmacodynamic effects, and these patients should be monitored closely for at least 48 hours following ingestion.14

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Verapamil Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Beta-1 adrenergic receptor---(C;G) / (G;G)G > CEffect Directly StudiedPatients with this genotype require a lower dosage of verapamil to achieve a favourable rate-control response when treating atrial fibrillation.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Verapamil.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Verapamil.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Verapamil is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Verapamil can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Verapamil can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Verapamil can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Verapamil.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Verapamil.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Verapamil.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Verapamil.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Avoid alcohol. Verapamil significantly inhibits the elimination of alcohol, leading to elevated blood alcohol levels.
  • Avoid grapefruit products. Co-administration with grapefruit may significantly increase serum concentrations.
  • Take with or without food. Recommendations vary from product to product - consult individual product monographs for additional information.

References

Synthesis Reference

Philippe Baudier, Arthur De Boeck, Jacques Fossion, "Novel galenic forms of verapamil, their preparation and medicines containing said novel galenic forms." U.S. Patent US4859469, issued April, 1987.

US4859469
General References
  1. Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. [PubMed:8725386]
  2. Ahmed JH, Meredith PA, Elliott HL: The influence of age on the pharmacokinetics of verapamil. Pharmacol Res. 1991 Oct;24(3):227-33. doi: 10.1016/1043-6618(91)90085-c. [PubMed:1956867]
  3. Dadashzadeh S, Javadian B, Sadeghian S: The effect of gender on the pharmacokinetics of verapamil and norverapamil in human. Biopharm Drug Dispos. 2006 Oct;27(7):329-34. doi: 10.1002/bdd.512. [PubMed:16892180]
  4. Tfelt-Hansen P, Tfelt-Hansen J: Verapamil for cluster headache. Clinical pharmacology and possible mode of action. Headache. 2009 Jan;49(1):117-25. doi: 10.1111/j.1526-4610.2008.01298.x. [PubMed:19125880]
  5. Busse D, Fromm MF, Morike K, Drescher S, Kuhlkamp V, Eichelbaum M: Disposition and pharmacologic effects of R/S-verapamil in patients with chronic atrial fibrillation: an investigation comparing single and multiple dosing. Clin Pharmacol Ther. 2001 May;69(5):324-32. doi: 10.1067/mcp.2001.115125. [PubMed:11372000]
  6. Ninomiya T, Takano M, Haruna T, Kono Y, Horie M: Verapamil, a Ca2+ entry blocker, targets the pore-forming subunit of cardiac type KATP channel (Kir6.2). J Cardiovasc Pharmacol. 2003 Aug;42(2):161-8. doi: 10.1097/00005344-200308000-00002. [PubMed:12883317]
  7. Bergson P, Lipkind G, Lee SP, Duban ME, Hanck DA: Verapamil block of T-type calcium channels. Mol Pharmacol. 2011 Mar;79(3):411-9. doi: 10.1124/mol.110.069492. Epub 2010 Dec 13. [PubMed:21149638]
  8. Perez-Reyes E, Van Deusen AL, Vitko I: Molecular pharmacology of human Cav3.2 T-type Ca2+ channels: block by antihypertensives, antiarrhythmics, and their analogs. J Pharmacol Exp Ther. 2009 Feb;328(2):621-7. doi: 10.1124/jpet.108.145672. Epub 2008 Oct 30. [PubMed:18974361]
  9. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  10. Striessnig J, Ortner NJ, Pinggera A: Pharmacology of L-type Calcium Channels: Novel Drugs for Old Targets? Curr Mol Pharmacol. 2015;8(2):110-22. [PubMed:25966690]
  11. Shibata K, Hirasawa A, Foglar R, Ogawa S, Tsujimoto G: Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors. Circulation. 1998 Apr 7;97(13):1227-30. [PubMed:9570190]
  12. Motulsky HJ, Snavely MD, Hughes RJ, Insel PA: Interaction of verapamil and other calcium channel blockers with alpha 1- and alpha 2-adrenergic receptors. Circ Res. 1983 Feb;52(2):226-31. [PubMed:6297831]
  13. Echizen H, Eichelbaum M: Clinical pharmacokinetics of verapamil, nifedipine and diltiazem. Clin Pharmacokinet. 1986 Nov-Dec;11(6):425-49. doi: 10.2165/00003088-198611060-00002. [PubMed:3542336]
  14. FDA Approved Drug Products: Verelan® PM extended-release capsules [Link]
  15. FDA Approved Drug Products: Verapamil HCl for intravenous injection [Link]
  16. Verapamil FDA Label [Link]
  17. FDA Approved Drugs: Tarka® extended-release tablets [Link]
  18. CaymanChem: Verapamil MSDS [Link]
  19. FDA Approved Drug Products: Calan SR tablets [Link]
External Links
Human Metabolome Database
HMDB0001850
KEGG Drug
D02356
KEGG Compound
C07188
PubChem Compound
2520
PubChem Substance
46508158
ChemSpider
2425
BindingDB
81939
RxNav
11170
ChEBI
77733
ChEMBL
CHEMBL6966
Therapeutic Targets Database
DAP000040
PharmGKB
PA451868
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Verapamil
ATC Codes
C09BB10 — Trandolapril and verapamilC08DA51 — Verapamil, combinationsC08DA01 — Verapamil
AHFS Codes
  • 24:28.92 — Miscellaneous Calcium-channel Blocking Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableCrohn's Disease (CD)1
1CompletedNot AvailableHealthy Volunteers5
1CompletedNot AvailableSubstance, Addiction1
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of ASP015K1
1CompletedBasic ScienceOpioid Dependence1
1CompletedBasic SciencePharmacokinetics1
1CompletedBasic ScienceSubstance, Addiction1
1CompletedDiagnosticChronic Subjective Dizziness / Vestibular Migraine1
1CompletedOtherDrug-induced QT Interval Prolongation / Pharmacodynamics / Pharmacokinetics1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentDrug-induced Surface ECG Changes1
1CompletedTreatmentHealthy Adult Subjects1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentIdiopathic Thrombocytopenic Purpura1
1CompletedTreatmentInfections, Respiratory Syncytial Virus1
1CompletedTreatmentStroke, Ischemic1
1CompletedTreatmentType 2 Diabetes Mellitus1
1RecruitingBasic ScienceCardiovascular System Disease / Drug-Related Side Effects and Adverse Reactions1
1RecruitingTreatmentCD30-Positive Neoplastic Cells Present / Recurrent Hodgkin Lymphoma / Refractory Hodgkin Lymphoma1
1RecruitingTreatmentStroke, Ischemic2
1TerminatedTreatmentPolyps, Nasal / Sinusitis1
1WithdrawnTreatmentStroke, Ischemic1
1, 2CompletedHealth Services ResearchHealthy Volunteers1
1, 2TerminatedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentBrain Cancer / Malignancies / Meningiomas1
2CompletedTreatmentDravet Syndrome1
2CompletedTreatmentType 1 Diabetes Mellitus1
2TerminatedPreventionEpisodic Cluster Headache1
2Unknown StatusDiagnosticEpilepsies1
2, 3CompletedTreatmentCluster Headache1
2, 3RecruitingTreatmentArrhythmia of ventricular origin1
3CompletedTreatmentArrhythmia / Atrial Fibrillation (AF) / Cardiovascular Heart Disease / Heart Diseases1
3CompletedTreatmentAtrial Fibrillation (AF)1
3CompletedTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
3CompletedTreatmentMania1
3Not Yet RecruitingTreatmentType1 Diabetes1
3TerminatedTreatmentAtrial Fibrillation (AF) / Heart Failure1
4CompletedPreventionKidney Stones1
4CompletedTreatmentAcute Myocardial Infarction (AMI) / Percutaneous Coronary Intervention (PCI)1
4CompletedTreatmentBMI >30 kg/m2 / General Surgery / Hypoglycemia1
4CompletedTreatmentCoronary Artery Disease / High Blood Pressure (Hypertension)1
4CompletedTreatmentDiabetes / High Blood Pressure (Hypertension)1
4CompletedTreatmentDiabetes / High Blood Pressure (Hypertension) / Proteinuria1
4CompletedTreatmentHeart Disease, Ischemic1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
4CompletedTreatmentMarfan Syndrome1
4CompletedTreatmentParoxysmal Supraventricular Tachycardia1
4CompletedTreatmentRapid Ventricular Response Atrial Fibrillation1
4Not Yet RecruitingOtherAtrial Fibrillation (AF)1
4RecruitingDiagnosticPremature Ventricular Contraction (PVC)1
4RecruitingHealth Services ResearchCerebral Vasospasm1
4TerminatedPreventionKeloid Scars1
4Unknown StatusTreatmentCardiomyopathy / Heart Failure With Reduced Ejection Fraction (HFrEF) / Myocardial Diseases1
4Unknown StatusTreatmentCongestive Cardiomyopathy1
4WithdrawnTreatmentReversible cerebral vasoconstriction syndrome1
Not AvailableCompletedNot AvailableCoronary Heart Disease (CHD) / Verapamil Toxicity1
Not AvailableCompletedNot AvailableErectile Dysfunction1
Not AvailableCompletedTreatmentArrhythmia / Atrial Fibrillation (AF)1
Not AvailableCompletedTreatmentAtrial Fibrillation (AF)1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableNot Yet RecruitingTreatmentTachycardia, Supraventricular1
Not AvailableRecruitingTreatmentVentricular premature beats1
Not AvailableTerminatedTreatmentPolyps, Nasal / Sinusitis1
Not AvailableUnknown StatusTreatmentEpilepsies / Seizures1
Not AvailableWithdrawnTreatmentCatamenial Epilepsy1

Pharmacoeconomics

Manufacturers
  • Mylan pharmaceuticals inc
  • Elan drug delivery inc
  • Gd searle llc
  • Fsc laboratories inc
  • Abraxis pharmaceutical products
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • International medication system
  • Luitpold pharmaceuticals inc
  • Marsam pharmaceuticals llc
  • Smith and nephew solopak div smith and nephew
  • Solopak medical products inc
  • Ranbaxy laboratories inc
  • Glenmark generics ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Par pharmaceutical inc
  • Pliva inc
  • Actavis elizabeth llc
  • Heritage pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Sandoz inc
  • Warner chilcott div warner lambert co
  • Watson laboratories inc
Packagers
  • Abbott Laboratories Ltd.
  • Advanced Pharmaceutical Services Inc.
  • Alza Corp.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • BASF Corp.
  • Cardinal Health
  • Caremark LLC
  • Comprehensive Consultant Services Inc.
  • Copley Chemical Co.
  • Dee Stevens and Son Feeder
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Elan Pharmaceuticals Inc.
  • FSC Laboratories
  • GD Searle LLC
  • General Injectables and Vaccines Inc.
  • Glenmark Generics Ltd.
  • Golden State Medical Supply Inc.
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Ranbaxy Laboratories
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • Talbert Medical Management Corp.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral
Tablet, extended releaseOral180 mg
Tablet, extended releaseOral240 mg
Tablet, coatedOral120 mg/1
Tablet, coatedOral180 mg/1
Tablet, coatedOral240 mg/1
Tablet, extended releaseOral120 mg
Tablet, extended releaseOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
InjectionIntravenous5 mg/1mL
Capsule, delayed release pelletsOral120 mg/1
Capsule, delayed release pelletsOral180 mg/1
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral120 mg/1
Capsule, extended releaseOral180 mg/1
Capsule, extended releaseOral200 mg/1
Capsule, extended releaseOral240 mg/1
Capsule, extended releaseOral300 mg/1
InjectionIntravenous10 mg/4mL
InjectionIntravenous2.5 mg/1mL
InjectionIntravenous5 mg/2mL
Injection, solutionIntravenous2.5 mg/1 mL
Injection, solutionIntravenous2.5 mg/1mL
PowderNot applicable1 kg/1kg
TabletOral120 mg/1
TabletOral180 mg/1
TabletOral240 mg/1
TabletOral40 mg/1
TabletOral80 mg/1
Tablet, extended releaseOral120 mg/1
Tablet, extended releaseOral180 mg/1
Tablet, extended releaseOral240 mg/301
Tablet, extended releaseOral240 mg/1
Tablet, film coatedOral120 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral80 mg/1
Tablet, film coated, extended releaseOral120 mg/1
Tablet, film coated, extended releaseOral180 mg/1
Tablet, film coated, extended releaseOral240 mg/1
LiquidIntravenous
SolutionIntravenous
Capsule, delayed release pelletsOral240 mg/1
Capsule, delayed release pelletsOral360 mg/1
Capsule, extended releaseOral120 mg
Capsule, extended releaseOral180 mg
Capsule, extended releaseOral240 mg
Prices
Unit descriptionCostUnit
Verelan 360 mg 24 Hour Capsule6.82USD capsule
Verelan 360 mg cap pellet6.73USD pellet
Verelan pm 300 mg cap pellet5.87USD pellet
Verelan 240 mg 24 Hour Capsule4.76USD capsule
Verelan 240 mg cap pellet4.58USD pellet
Verelan 180 mg 24 Hour Capsule4.22USD capsule
Verelan 180 mg cap pellet4.06USD pellet
Verelan pm 200 mg cap pellet4.04USD pellet
Verelan 120 mg cap pellet3.87USD pellet
Verapamil HCl CR 300 mg 24 Hour Capsule3.82USD capsule
Isoptin sr 240 mg tablet3.32USD tablet
Verapamil hcl powder3.24USD g
Calan SR 240 mg Controlled Release Tabs3.15USD tab
Isoptin SR 240 mg Controlled Release Tabs3.14USD tab
Verelan pm 100 mg cap pellet3.13USD pellet
Calan sr 240 mg caplet3.09USD caplet
Covera-HS 240 mg 24 Hour tablet3.09USD tablet
Covera-hs 240 mg tablet sa2.97USD tablet
Isoptin sr 180 mg tablet2.9USD tablet
Calan SR 180 mg Controlled Release Tabs2.8USD tab
Isoptin SR 180 mg Controlled Release Tabs2.74USD tab
Calan sr 180 mg caplet2.7USD caplet
Verapamil HCl CR 200 mg 24 Hour Capsule2.62USD capsule
Isoptin sr 120 mg tablet2.29USD tablet
Calan SR 120 mg Controlled Release Tabs2.27USD tab
Covera-HS 180 mg 24 Hour tablet2.2USD tablet
Isoptin SR 120 mg Controlled Release Tabs2.16USD tab
Calan sr 120 mg caplet2.13USD caplet
Covera-hs 180 mg tablet sa2.11USD tablet
Verapamil HCl CR 360 mg 24 Hour Capsule2.1USD capsule
Verapamil HCl CR 100 mg 24 Hour Capsule2.04USD capsule
Isoptin Sr 240 mg Sustained-Release Tablet2.03USD tablet
Calan sr 240 mg caplet sa1.77USD caplet
Verapamil HCl CR 240 mg 24 Hour Capsule1.69USD capsule
Verapamil HCl CR 240 mg Controlled Release Tabs1.6USD tab
Calan 120 mg tablet1.56USD tablet
Isoptin Sr 180 mg Sustained-Release Tablet1.52USD tablet
Verapamil HCl CR 180 mg 24 Hour Capsule1.5USD capsule
Calan sr 180 mg caplet sa1.46USD caplet
Verapamil HCl CR 120 mg 24 Hour Capsule1.43USD capsule
Verapamil HCl CR 180 mg Controlled Release Tabs1.41USD tab
Isoptin Sr 120 mg Sustained-Release Tablet1.34USD tablet
Calan 80 mg tablet1.25USD tablet
Verapamil 2.5 mg/ml vial1.18USD ml
Verapamil HCl CR 120 mg Controlled Release Tabs1.12USD tab
Apo-Verap Sr 240 mg Sustained-Release Tablet0.91USD tablet
Mylan-Verapamil Sr 240 mg Sustained-Release Tablet0.91USD tablet
Novo-Veramil Sr 240 mg Sustained-Release Tablet0.91USD tablet
Pms-Verapamil Sr 240 mg Sustained-Release Tablet0.91USD tablet
Calan 40 mg tablet0.76USD tablet
Apo-Verap Sr 120 mg Sustained-Release Tablet0.72USD tablet
Mylan-Verapamil Sr 120 mg Sustained-Release Tablet0.72USD tablet
Verapamil HCl 120 mg tablet0.71USD tablet
Apo-Verap Sr 180 mg Sustained-Release Tablet0.69USD tablet
Mylan-Verapamil Sr 180 mg Sustained-Release Tablet0.69USD tablet
Verapamil HCl 80 mg tablet0.56USD tablet
Apo-Verap 120 mg Tablet0.45USD tablet
Mylan-Verapamil 120 mg Tablet0.45USD tablet
Nu-Verap 120 mg Tablet0.45USD tablet
Verapamil 120 mg tablet0.39USD tablet
Verapamil 80 mg tablet0.31USD tablet
Verapamil HCl 40 mg tablet0.29USD tablet
Apo-Verap 80 mg Tablet0.29USD tablet
Mylan-Verapamil 80 mg Tablet0.29USD tablet
Nu-Verap 80 mg Tablet0.29USD tablet
Verapamil 40 mg tablet0.28USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5785994No1998-07-282009-10-22Us
US6096339No2000-08-012017-04-04Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00394 mg/mLALOGPS
logP5.23ALOGPS
logP5.04ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.95 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity132.65 m3·mol-1ChemAxon
Polarizability51.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9371
Blood Brain Barrier+0.6323
Caco-2 permeable+0.738
P-glycoprotein substrateSubstrate0.7874
P-glycoprotein inhibitor IInhibitor0.9056
P-glycoprotein inhibitor IIInhibitor0.855
Renal organic cation transporterInhibitor0.6259
CYP450 2C9 substrateNon-substrate0.8029
CYP450 2D6 substrateNon-substrate0.8706
CYP450 3A4 substrateSubstrate0.7657
CYP450 1A2 substrateNon-inhibitor0.9553
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9181
Ames testNon AMES toxic0.8393
CarcinogenicityNon-carcinogens0.6463
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.4137 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7687
hERG inhibition (predictor II)Inhibitor0.8188
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0udi-3519000000-b5e0b9e0caac5cb57222
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-004l-0702900000-6a46ea2d5eed6d8b01eb
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0006-4109800000-80d342090a0be3344e82
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-054w-0954400000-2def387c7c93ab211423
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0a4i-0000900000-4cde9a4b3a4f83d16afc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0a4i-0000900000-980b47834e505d54a0e6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-066r-0902800000-ae024239c46b33917426
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-0901000000-81d1159b3102cff76218
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-0900000000-d9c344fee7b45b4030e6
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0gb9-0914000000-070bdb975910e9aae99c
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-03di-0390000000-f41d80462c5d06c4f001
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0097-2980000000-9a2ab0bcab33f7eaac6b
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0uxr-0900000000-252a9989a8511cb2db80
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0f79-0900000000-4fd6ca2c6c19c3bbf8f0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0000900000-4365a47b2dc2f86bb272
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0000900000-e6a2b357160bf5b92c22
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-066r-0902400000-d8eac2ccd0a767c7e432
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0901000000-688f3c2345c5d9ccb8a5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-cd09f8a2be876936f662
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0918000000-76641dd6dbc5cb05e79a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0000900000-05ea95eb1f39b6515212
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-066r-0902600000-a675e624692c25472ce8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0901000000-70d820628d2613557239
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0gb9-0900000000-e3ca24cf75d574df08a8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uyi-0900000000-f3a9fa002c56d3e5689a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zg0-2900000000-101e077b890671063633
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0000900000-84b4516ac84e6912cc15
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-066r-0902600000-bc1701c307e45ee4dcd7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0901000000-6fbdab598bcb6147a4bf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0gb9-0900000000-ce61116806eaa908681c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0900000000-ad3f25e02a7c8e66fb6a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zgr-2900000000-792b9009086561f6c398
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0918000000-e7a5a3f8c88dc40683fd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0000900000-4cde9a4b3a4f83d16afc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0000900000-9a5c5240148f82cc6add
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-066r-0902800000-ae024239c46b33917426
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0901000000-81d1159b3102cff76218
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-2411d65dfe09741dde81
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0gb9-0914000000-0463345a8ab0de7aa99e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-42074ab645b7af0ef79f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zgi-0900000000-20360f78435d5f482709
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0819000000-7f68ebd6e344adf12101
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0918000000-d3727bbe601b80eabfb3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0100900000-0a928f78000f291f031d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-066r-0902600000-40f800e4a364d9ca214c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gb9-0900000000-4dea228d69d59705fc18
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0500900000-c0bc440571b30d4b5b27
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-066r-0900300000-47a59c15bdbcbc62d6c6
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Dimethoxybenzenes / Phenylpropanes / Phenethylamines / Phenoxy compounds / Anisoles / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Nitriles / Organopnictogen compounds
show 1 more
Substituents
Phenylbutylamine / Dimethoxybenzene / O-dimethoxybenzene / Phenethylamine / Phenylpropane / Anisole / Phenol ether / Phenoxy compound / Methoxybenzene / Alkyl aryl ether
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, aromatic ether, nitrile, polyether (CHEBI:77733)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium 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, hor...
Gene Name
CACNA1C
Uniprot ID
Q13936
Uniprot Name
Voltage-dependent L-type calcium channel subunit alpha-1C
Molecular Weight
248974.1 Da
References
  1. Dilmac N, Hilliard N, Hockerman GH: Molecular determinants of frequency dependence and Ca2+ potentiation of verapamil block in the pore region of Cav1.2. Mol Pharmacol. 2004 Nov;66(5):1236-47. Epub 2004 Jul 30. [PubMed:15286207]
  2. Morel N, Buryi V, Feron O, Gomez JP, Christen MO, Godfraind T: The action of calcium channel blockers on recombinant L-type calcium channel alpha1-subunits. Br J Pharmacol. 1998 Nov;125(5):1005-12. [PubMed:9846638]
  3. Patel MK, Clunn GF, Lymn JS, Austin O, Hughes AD: Effect of serum withdrawal on the contribution of L-type calcium channels (CaV1.2) to intracellular Ca2+ responses and chemotaxis in cultured human vascular smooth muscle cells. Br J Pharmacol. 2005 Jul;145(6):811-7. [PubMed:15880143]
  4. Tfelt-Hansen P, Tfelt-Hansen J: Verapamil for cluster headache. Clinical pharmacology and possible mode of action. Headache. 2009 Jan;49(1):117-25. doi: 10.1111/j.1526-4610.2008.01298.x. [PubMed:19125880]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated calcium 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, hor...
Gene Name
CACNA1B
Uniprot ID
Q00975
Uniprot Name
Voltage-dependent N-type calcium channel subunit alpha-1B
Molecular Weight
262493.84 Da
References
  1. Dobrev D, Milde AS, Andreas K, Ravens U: The effects of verapamil and diltiazem on N-, P- and Q-type calcium channels mediating dopamine release in rat striatum. Br J Pharmacol. 1999 May;127(2):576-82. doi: 10.1038/sj.bjp.0702574. [PubMed:10385261]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated calcium 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, hor...
Gene Name
CACNA1A
Uniprot ID
O00555
Uniprot Name
Voltage-dependent P/Q-type calcium channel subunit alpha-1A
Molecular Weight
282362.39 Da
References
  1. Dobrev D, Milde AS, Andreas K, Ravens U: The effects of verapamil and diltiazem on N-, P- and Q-type calcium channels mediating dopamine release in rat striatum. Br J Pharmacol. 1999 May;127(2):576-82. doi: 10.1038/sj.bjp.0702574. [PubMed:10385261]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated 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 ...
Gene Name
KCNJ11
Uniprot ID
Q14654
Uniprot Name
ATP-sensitive inward rectifier potassium channel 11
Molecular Weight
43540.375 Da
References
  1. Ninomiya T, Takano M, Haruna T, Kono Y, Horie M: Verapamil, a Ca2+ entry blocker, targets the pore-forming subunit of cardiac type KATP channel (Kir6.2). J Cardiovasc Pharmacol. 2003 Aug;42(2):161-8. doi: 10.1097/00005344-200308000-00002. [PubMed:12883317]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Scaffold protein binding
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, hor...
Gene Name
CACNA1G
Uniprot ID
O43497
Uniprot Name
Voltage-dependent T-type calcium channel subunit alpha-1G
Molecular Weight
262468.62 Da
References
  1. Freeze BS, McNulty MM, Hanck DA: State-dependent verapamil block of the cloned human Ca(v)3.1 T-type Ca(2+) channel. Mol Pharmacol. 2006 Aug;70(2):718-26. Epub 2006 May 12. [PubMed:16699084]
  2. Bergson P, Lipkind G, Lee SP, Duban ME, Hanck DA: Verapamil block of T-type calcium channels. Mol Pharmacol. 2011 Mar;79(3):411-9. doi: 10.1124/mol.110.069492. Epub 2010 Dec 13. [PubMed:21149638]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Scaffold protein binding
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, hor...
Gene Name
CACNA1H
Uniprot ID
O95180
Uniprot Name
Voltage-dependent T-type calcium channel subunit alpha-1H
Molecular Weight
259160.2 Da
References
  1. Perez-Reyes E, Van Deusen AL, Vitko I: Molecular pharmacology of human Cav3.2 T-type Ca2+ channels: block by antihypertensives, antiarrhythmics, and their analogs. J Pharmacol Exp Ther. 2009 Feb;328(2):621-7. doi: 10.1124/jpet.108.145672. Epub 2008 Oct 30. [PubMed:18974361]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
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 ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Duan JJ, Ma JH, Zhang PH, Wang XP, Zou AR, Tu DN: Verapamil blocks HERG channel by the helix residue Y652 and F656 in the S6 transmembrane domain. Acta Pharmacol Sin. 2007 Jul;28(7):959-67. [PubMed:17588331]
  2. Schneider J, Hauser R, Andreas JO, Linz K, Jahnel U: Differential effects of human ether-a-go-go-related gene (HERG) blocking agents on QT duration variability in conscious dogs. Eur J Pharmacol. 2005 Apr 4;512(1):53-60. [PubMed:15814090]
  3. Tfelt-Hansen P, Tfelt-Hansen J: Verapamil for cluster headache. Clinical pharmacology and possible mode of action. Headache. 2009 Jan;49(1):117-25. doi: 10.1111/j.1526-4610.2008.01298.x. [PubMed:19125880]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Unknown
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  2. Brown NL, Sirugue O, Worcel M: The effects of some slow channel blocking drugs on high affinity serotonin uptake by rat brain synaptosomes. Eur J Pharmacol. 1986 Apr 9;123(1):161-5. [PubMed:2940099]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Inhibits receptor activity but shows little competition for binding. Likely an allosteric modulator.
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Shibata K, Hirasawa A, Foglar R, Ogawa S, Tsujimoto G: Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors. Circulation. 1998 Apr 7;97(13):1227-30. [PubMed:9570190]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Inhibits receptor activity but shows little competition for binding. Likely an allosteric modulator.
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Shibata K, Hirasawa A, Foglar R, Ogawa S, Tsujimoto G: Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors. Circulation. 1998 Apr 7;97(13):1227-30. [PubMed:9570190]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Inhibits receptor activity but shows little competition for binding. Likely an allosteric modulator.
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Shibata K, Hirasawa A, Foglar R, Ogawa S, Tsujimoto G: Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors. Circulation. 1998 Apr 7;97(13):1227-30. [PubMed:9570190]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase 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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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. doi: 10.1124/dmd.104.001834. Epub 2005 Feb 2. [PubMed:15689501]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase 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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Totah RA, Rettie AE: Cytochrome P450 2C8: substrates, inhibitors, pharmacogenetics, and clinical relevance. Clin Pharmacol Ther. 2005 May;77(5):341-52. doi: 10.1016/j.clpt.2004.12.267. [PubMed:15900280]
  2. Busse D, Cosme J, Beaune P, Kroemer HK, Eichelbaum M: Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21. doi: 10.1007/bf00168924. [PubMed:8750925]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase 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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. 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. doi: 10.1124/dmd.104.001834. Epub 2005 Feb 2. [PubMed:15689501]
  2. Langaee TY, Gong Y, Yarandi HN, Katz DA, Cooper-DeHoff RM, Pepine CJ, Johnson JA: Association of CYP3A5 polymorphisms with hypertension and antihypertensive response to verapamil. Clin Pharmacol Ther. 2007 Mar;81(3):386-91. doi: 10.1038/sj.clpt.6100090. [PubMed:17339868]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase 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 un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Activator
General Function
Steroid hydroxylase 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 un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Busse D, Cosme J, Beaune P, Kroemer HK, Eichelbaum M: Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21. doi: 10.1007/bf00168924. [PubMed:8750925]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Kroemer HK, Gautier JC, Beaune P, Henderson C, Wolf CR, Eichelbaum M: Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7. [PubMed:8232610]
  2. Zhou SF, Yang LP, Zhou ZW, Liu YH, Chan E: Insights into the substrate specificity, inhibitors, regulation, and polymorphisms and the clinical impact of human cytochrome P450 1A2. AAPS J. 2009 Sep;11(3):481-94. doi: 10.1208/s12248-009-9127-y. Epub 2009 Jul 10. [PubMed:19590965]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Verelan® PM extended-release capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. FDA Approved Drug Products: Verelan® PM extended-release capsules [Link]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Tfelt-Hansen P, Tfelt-Hansen J: Verapamil for cluster headache. Clinical pharmacology and possible mode of action. Headache. 2009 Jan;49(1):117-25. doi: 10.1111/j.1526-4610.2008.01298.x. [PubMed:19125880]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Cho SK, Kim CO, Park ES, Chung JY: Verapamil decreases the glucose-lowering effect of metformin in healthy volunteers. Br J Clin Pharmacol. 2014 Dec;78(6):1426-32. doi: 10.1111/bcp.12476. [PubMed:25060604]
  2. Boxberger KH, Hagenbuch B, Lampe JN: Common drugs inhibit human organic cation transporter 1 (OCT1)-mediated neurotransmitter uptake. Drug Metab Dispos. 2014 Jun;42(6):990-5. doi: 10.1124/dmd.113.055095. Epub 2014 Mar 31. [PubMed:24688079]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter 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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100]
  2. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Zeng H, Chen ZS, Belinsky MG, Rea PA, Kruh GD: Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32. [PubMed:11585759]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Oostendorp RL, van de Steeg E, van der Kruijssen CM, Beijnen JH, Kenworthy KE, Schinkel AH, Schellens JH: Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. Drug Metab Dispos. 2009 Apr;37(4):917-23. doi: 10.1124/dmd.108.024901. Epub 2009 Jan 12. [PubMed:19139163]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Perrotton T, Trompier D, Chang XB, Di Pietro A, Baubichon-Cortay H: (R)- and (S)-verapamil differentially modulate the multidrug-resistant protein MRP1. J Biol Chem. 2007 Oct 26;282(43):31542-8. doi: 10.1074/jbc.M703964200. Epub 2007 Jul 22. [PubMed:17646169]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [PubMed:12036927]
  2. Bai J, Lai L, Yeo HC, Goh BC, Tan TM: Multidrug resistance protein 4 (MRP4/ABCC4) mediates efflux of bimane-glutathione. Int J Biochem Cell Biol. 2004 Feb;36(2):247-57. [PubMed:14643890]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name
ABCC10
Uniprot ID
Q5T3U5
Uniprot Name
Multidrug resistance-associated protein 7
Molecular Weight
161627.375 Da
References
  1. Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [PubMed:12527806]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Radchenko M, Symersky J, Nie R, Lu M: Structural basis for the blockade of MATE multidrug efflux pumps. Nat Commun. 2015 Aug 6;6:7995. doi: 10.1038/ncomms8995. [PubMed:26246409]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. Radchenko M, Symersky J, Nie R, Lu M: Structural basis for the blockade of MATE multidrug efflux pumps. Nat Commun. 2015 Aug 6;6:7995. doi: 10.1038/ncomms8995. [PubMed:26246409]

Drug created on June 13, 2005 07:24 / Updated on April 03, 2020 10:26

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