Identification

Name
Nifedipine
Accession Number
DB01115  (APRD00590)
Type
Small Molecule
Groups
Approved
Description

Nifedipine has been formulated as both a long- and short-acting 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nifedipine prevents calcium-dependent myocyte contraction and vasoconstriction. A second proposed mechanism for the drug’s vasodilatory effects involves pH-dependent inhibition of calcium influx via inhibition of smooth muscle carbonic anhydrase. Nifedipine is used to treat hypertension and chronic stable angina.

Structure
Thumb
Synonyms
  • 4-(2'-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethylester
  • Adapine
  • Nifecard
  • Nifecor
  • Nifedipine
  • Nifedipino
  • Nifedipinum
  • Nifedipres
External IDs
BAY A 1040
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdalatCapsule5 mgOralBayer1997-01-072005-07-27Canada
Adalat - Cap 10mgCapsule10 mgOralBayer1982-12-312005-07-27Canada
Adalat Cap 10mgCapsule10 mgOralMiles Inc. Pharmaceutical Division1982-12-312000-08-01Canada
Adalat Cap 5mgCapsule5 mgOralMiles Inc. Pharmaceutical Division1986-12-312000-08-01Canada
Adalat CCTablet, film coated90 mg/1OralSchering Corporation2011-02-282013-07-01Us0085 172220180907 15195 xvoagd
Adalat CCTablet, film coated90 mg/1OralBayer1993-04-212017-11-10Us
Adalat CCTablet, film coated90 mg/1OralPhysicians Total Care, Inc.1994-07-112011-06-30Us
Adalat CCTablet, film coated90 mg/1OralALMATICA PHARMA INC.2017-02-01Not applicableUs
Adalat CCTablet, film coated30 mg/1OralPhysicians Total Care, Inc.1993-09-082012-06-30Us
Adalat CCTablet, film coated30 mg/1OralALMATICA PHARMA INC.2017-02-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Afeditab CRTablet, film coated, extended release60 mg/1OralAphena Pharma Solutions Tennessee, Inc.2002-11-01Not applicableUs
Afeditab CRTablet, film coated, extended release30 mg/1OralCarilion Materials Management2002-11-01Not applicableUs00591 3193 01 nlmimage10 6d46b6f5
Afeditab CRTablet, film coated, extended release30 mg/1OralActavis Pharma, Inc.2002-11-012019-01-31Us0591 319320180907 15195 7gza2p
Afeditab CRTablet, film coated, extended release60 mg/1OralActavis Pharma, Inc.2002-11-012018-11-30Us
Afeditab CRTablet, film coated, extended release60 mg/1Oralbryant ranch prepack2002-11-012018-10-23Us
Afeditab CRTablet, film coated, extended release30 mg/1OralAphena Pharma Solutions Tennessee, Inc.2002-11-01Not applicableUs
Apo-nifed PaTablet, extended release20 mgOralApotex Corporation1995-12-31Not applicableCanada
Apo-nifed PaTablet, extended release10 mgOralApotex Corporation1995-12-31Not applicableCanada
Dom-nifedipineCapsule5 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-nifedipineCapsule10 mgOralDominion PharmacalNot applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adalat XL PlusNifedipine (20 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet, delayed release; Tablet, extended releaseOralBayer2008-07-242014-07-18Canada
Adalat XL PlusNifedipine (60 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet, delayed release; Tablet, extended releaseOralBayer2008-07-242014-07-18Canada
Adalat XL PlusNifedipine (30 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet, delayed release; Tablet, extended releaseOralBayer2008-07-242014-07-18Canada
International/Other Brands
Adalat / Adapine / Afeditab / Coracten / Nifecard / Nifecor / Nifedical / NifedicalXL / Nifedipres / Procardia
Categories
UNII
I9ZF7L6G2L
CAS number
21829-25-4
Weight
Average: 346.3346
Monoisotopic: 346.116486318
Chemical Formula
C17H18N2O6
InChI Key
HYIMSNHJOBLJNT-UHFFFAOYSA-N
InChI
InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3
IUPAC Name
3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
SMILES
COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OC

Pharmacology

Indication

For the management of vasospastic angina, chronic stable angina, hypertension, and Raynaud's phenomenon. May be used as a first line agent for left ventricular hypertrophy and isolated systolic hypertension (long-acting agents).

Associated Conditions
Pharmacodynamics

Nifedipine, the prototype of the dihydropyridine class of calcium channel blockers (CCBs), is similar to other dihydropyridines including amlodipine, felodipine, isradipine, and nicardipine. There are at least five different types of calcium channels in Homo sapiens: L-, N-, P/Q-, R- and T-type. CCBs target L-type calcium channels, the major channel in muscle cells that mediates contraction. Similar to other DHP CCBs, nifedipine binds directly to inactive calcium channels stabilizing their inactive conformation. Since arterial smooth muscle depolarizations are longer in duration than cardiac muscle depolarizations, inactive channels are more prevalent in smooth muscle cells. Alternative splicing of the alpha-1 subunit of the channel gives nifedipine additional arterial selectivity. At therapeutic sub-toxic concentrations, nifedipine has little effect on cardiac myocytes and conduction cells. By blocking the calcium channels, Nifedipine inhibits the spasm of the coronary artery and dilates the systemic arteries, results in a increase of myocardial oxygen supply and a decrease in systemic blood pressure.

Mechanism of action

Nifedipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes the phosphorylation of the regulatory light chain subunit of myosin, a key step in muscle contraction. Signal amplification is achieved by calcium-induced calcium release from the sarcoplasmic reticulum through ryanodine receptors. Inhibition of the initial influx of calcium inhibits the contractile processes of smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload. The vasodilatory effects of nifedipine result in an overall decrease in blood pressure.

TargetActionsOrganism
AVoltage-dependent L-type calcium channel subunit alpha-1C
inhibitor
Human
AVoltage-dependent calcium channel subunit alpha-2/delta-1
inhibitor
Human
AVoltage-dependent L-type calcium channel subunit beta-2
inhibitor
Human
AVoltage-dependent L-type calcium channel subunit alpha-1D
inhibitor
Human
AVoltage-dependent L-type calcium channel subunit alpha-1S
inhibitor
Human
UCalmodulin
inhibitor
Human
UPotassium voltage-gated channel subfamily A member 1
inhibitor
Human
UVoltage-dependent T-type calcium channel subunit alpha-1H
inhibitor
Human
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
Absorption

Rapidly and fully absorbed following oral administration.

Volume of distribution
Not Available
Protein binding

92-98%

Metabolism

Hepatic metabolism via cytochrome P450 system. Predominantly metabolized by CYP3A4, but also by CYP1A2 and CYP2A6 isozymes.

Route of elimination

Nifedipine is extensively metabolized to highly water-soluble, inactive metabolites accounting for 60 to 80% of the dose excreted in the urine. The remainder is excreted in the feces in metabolized form, most likely as a result of biliary excretion.

Half life

2 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include dizziness, drowsiness, nausea, severe drop in blood pressure, slurred speech, and weakness. LD50=494 mg/kg (orally in mice); LD50=1022 mg/kg (orally in rats)

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Nifedipine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Nifedipine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Nifedipine.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Nifedipine is combined with 2,4-thiazolidinedione.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Nifedipine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Nifedipine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Nifedipine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nifedipine.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Nifedipine.
6-Deoxyerythronolide BThe metabolism of Nifedipine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Nifedipine.
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Grapefruit down-regulates post-translational expression of CYP3A4, the major metabolizing enzyme of nifedipine. Grapefruit, in all forms (e.g. whole fruit, juice and rind), can significantly increase serum levels of nifedipine and may cause toxicity. Avoid grapefruit products while on this medication.
  • Take with low fat meal.

References

Synthesis Reference

Hiroitsu Kawata, Tadayoshi Ohmura, Katsuhiko Yano, Mikio Matsumura, Saburo Higuchi, Yoshiaki Soeishi, "Nifedipine-containing solid preparation composition." U.S. Patent US4412986, issued November, 1976.

US4412986
General References
  1. Brown MJ, Palmer CR, Castaigne A, de Leeuw PW, Mancia G, Rosenthal T, Ruilope LM: Morbidity and mortality in patients randomised to double-blind treatment with a long-acting calcium-channel blocker or diuretic in the International Nifedipine GITS study: Intervention as a Goal in Hypertension Treatment (INSIGHT). Lancet. 2000 Jul 29;356(9227):366-72. [PubMed:10972368]
  2. Poole-Wilson PA, Kirwan BA, Voko Z, de Brouwer S, van Dalen FJ, Lubsen J: Safety of nifedipine GITS in stable angina: the ACTION trial. Cardiovasc Drugs Ther. 2006 Feb;20(1):45-54. [PubMed:16552473]
  3. Odou P, Ferrari N, Barthelemy C, Brique S, Lhermitte M, Vincent A, Libersa C, Robert H: Grapefruit juice-nifedipine interaction: possible involvement of several mechanisms. J Clin Pharm Ther. 2005 Apr;30(2):153-8. [PubMed:15811168]
  4. Grossman E, Messerli FH, Grodzicki T, Kowey P: Should a moratorium be placed on sublingual nifedipine capsules given for hypertensive emergencies and pseudoemergencies? JAMA. 1996 Oct 23-30;276(16):1328-31. [PubMed:8861992]
  5. Takahashi D, Oyunzul L, Onoue S, Ito Y, Uchida S, Simsek R, Gunduz MG, Safak C, Yamada S: Structure-activity relationships of receptor binding of 1,4-dihydropyridine derivatives. Biol Pharm Bull. 2008 Mar;31(3):473-9. [PubMed:18310913]
  6. Varon J, Marik PE: Clinical review: the management of hypertensive crises. Crit Care. 2003 Oct;7(5):374-84. Epub 2003 Jul 16. [PubMed:12974970]
External Links
Human Metabolome Database
HMDB0015247
KEGG Drug
D00437
KEGG Compound
C07266
PubChem Compound
4485
PubChem Substance
46505103
ChemSpider
4330
BindingDB
50101817
ChEBI
7565
ChEMBL
CHEMBL193
Therapeutic Targets Database
DAP000529
PharmGKB
PA450631
IUPHAR
2514
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nifedipine
ATC Codes
C08CA05 — NifedipineC08CA55 — Nifedipine, combinationsC08GA01 — Nifedipine and diuretics
AHFS Codes
  • 24:28.08 — Dihydropyridines
FDA label
Download (206 KB)
MSDS
Download (74.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentDermatomyositis / Lupus Erythematosus, Systemic / Raynaud Phenomenon Due to Trauma / Raynaud's Disease / System; Sclerosis / Ultrasound Therapy; Complications1
0RecruitingPreventionChronic Hypertension Complicating Pregnancy (Diagnosis) / Preeclampsia1
0RecruitingPreventionObesity, Morbid / Preeclampsia1
1CompletedNot AvailableBioavailability, Therapeutical Indication Not Studied1
1CompletedNot AvailableBioequivalence1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableHypertension,Essential1
1CompletedNot AvailableSubstance, Addiction1
1CompletedBasic ScienceChronic Kidney Disease (CKD) / Proteinuria1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentAcute iron intoxication / Hemochromatosis / Thalassaemic disorders1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1RecruitingTreatmentCytochrome P450 Interaction1
1, 2CompletedTreatmentCongenital Adrenal Hyperplasia (CAH)1
1, 2CompletedTreatmentObstetric Labour, Premature1
1, 2WithdrawnTreatmentHigh Blood Pressure (Hypertension) / Pregnancy Toxemias / Proteinuria1
2CompletedTreatmentAging / Cognitive Impairments / High Blood Pressure (Hypertension)1
2CompletedTreatmentChronic Kidney Disease (CKD) / CRD1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentPlacenta Previa1
2CompletedTreatmentPremature Labour1
2RecruitingTreatmentImplantation, Embryo1
2Unknown StatusPreventionPremature Labour1
2Unknown StatusTreatmentBlood Pressures / Chronic Kidney Disease (CKD) / Proteinuria1
2, 3CompletedPreventionCerebral Palsy (CP) / Premature Labour1
2, 3CompletedTreatmentChronic Anal Fissures1
2, 3RecruitingTreatmentHigh Blood Pressure (Hypertension)2
2, 3RecruitingTreatmentSevere Pre-Eclampsia, Antepartum1
3CompletedPreventionDiabetic Nephropathies1
3CompletedTreatmentCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia1
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / Raynaud's Disease / Vascular Diseases1
3CompletedTreatmentHigh Blood Pressure (Hypertension)3
3CompletedTreatmentPulmonary Hypertension (PH)1
3Not Yet RecruitingTreatmentLabor Preterm Multiple1
3Not Yet RecruitingTreatmentPostnatal Hypertension1
3RecruitingTreatmentPremature Labour1
3TerminatedTreatmentPremature Labour1
3Unknown StatusTreatmentObstetric Labour, Premature1
3Unknown StatusTreatmentRenal Stones1
3WithdrawnTreatmentPreterm Delivery1
3WithdrawnTreatmentThreatened Preterm Labor1
4Active Not RecruitingPreventionMountain Sickness1
4Active Not RecruitingTreatmentDrug Transporter1
4CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
4CompletedBasic SciencePremature Births1
4CompletedPreventionChronic Renal Failure (CRF) / Coronary Artery Disease1
4CompletedPreventionNonvalvular Atrial Fibrillation1
4CompletedPreventionPremature Births1
4CompletedSupportive CareManaging Preterm Labor1
4CompletedTreatmentHigh Blood Pressure (Hypertension)6
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Other and unspecified effects of high altitude1
4CompletedTreatmentHypertension in Pregnancy / Preeclampsia1
4CompletedTreatmentHypertension,Essential1
4CompletedTreatmentPremature Labour1
4RecruitingPreventionHypertension, Pregnancy-Induced / Prophylaxis of preeclampsia1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)2
4RecruitingTreatmentHypertension in Postpartum / Hypertension in Pregnancy1
4RecruitingTreatmentHypertension in Pregnancy / Preeclampsia1
4RecruitingTreatmentPremature Labour2
4Unknown StatusTreatmentHypertension,Essential1
4Unknown StatusTreatmentUrinary Tract Stones1
Not AvailableActive Not RecruitingNot AvailablePremature Labour1
Not AvailableActive Not RecruitingTreatmentObstetric Labour, Premature1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)2
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension) / Pregnancy / Prophylaxis of preeclampsia1
Not AvailableCompletedTreatmentObstetric Labour, Premature1
Not AvailableCompletedTreatmentObstetric Labour, Premature / Thrombosis, Venous1
Not AvailableCompletedTreatmentPhysiology, Ocular / Regional Blood Flow1
Not AvailableCompletedTreatmentPremature Labour1
Not AvailableCompletedTreatmentSevere Postpartum Hypertension1
Not AvailableRecruitingNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableRecruitingBasic ScienceEndothelium, Vascular1
Not AvailableTerminatedTreatmentPremature Births / Premature Labour1
Not AvailableTerminatedTreatmentPremature Labour1
Not AvailableWithdrawnTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableWithdrawnTreatmentLevator Ani Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bayer Healthcare
  • Biovail Pharmaceuticals
  • Bryant Ranch Prepack
  • Cardinal Health
  • Caremark LLC
  • Catalent Pharma Solutions
  • Comprehensive Consultant Services Inc.
  • Coupler Enterprises Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Elan Pharmaceuticals Inc.
  • Eurand Pharmaceuticals Inc.
  • Gavis Pharmaceuticals LLC
  • Giant Food Inc.
  • Goldline Laboratories Inc.
  • Greenstone LLC
  • H.E. Butt Grocery Co.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • International Laboratories Inc.
  • Ivax Pharmaceuticals
  • IVC Industries Inc.
  • Kaiser Foundation Hospital
  • LeaderPharma
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mason Distributors
  • Mckesson Corp.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Physicians Total Care Inc.
  • Prasco Labs
  • Pratt Pharmaceuticals
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • RP Scherer Canada Inc.
  • Sandhills Packaging Inc.
  • Schering Corp.
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Warrick Pharmaceuticals Corp.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral60 mg/1
Tablet, film coatedOral90 mg/1
TabletOral10 mg
TabletOral20 mg
Tablet, extended releaseOral20 mg
Tablet, extended releaseOral30 mg
Tablet, extended releaseOral60 mg
Kit; tablet, delayed release; tablet, extended releaseOral
Tablet, film coated, extended releaseOral90 mg/1
CapsuleOral10 mg/1
CapsuleOral10 mg
CapsuleOral20 mg/1
CapsuleOral5 mg
Capsule, liquid filledOral10 mg/1
Capsule, liquid filledOral20 mg/1
TabletOral30 mg/1
Tablet, extended releaseOral30 mg/1
Tablet, extended releaseOral60 mg/1
Tablet, film coated, extended releaseOral30 mg/1
Tablet, film coated, extended releaseOral60 mg/1
Tablet, extended releaseOral90 mg/1
Tablet, extended releaseOral10 mg
CapsuleOral20 mg/1mL
Prices
Unit descriptionCostUnit
Nifedipine powder15.3USD g
Procardia XL 90 mg 24 Hour tablet4.77USD tablet
Procardia xl 90 mg tablet4.58USD tablet
Procardia xl 60 mg tablet4.43USD tablet
Procardia XL 60 mg 24 Hour tablet4.13USD tablet
Adalat CC 90 mg 24 Hour tablet3.5USD tablet
Adalat cc 90 mg tablet3.37USD tablet
Adalat CC 60 mg 24 Hour tablet2.99USD tablet
Adalat cc 60 mg tablet2.87USD tablet
NIFEdipine CR Osmotic 90 mg 24 Hour tablet2.66USD tablet
Nifediac cc 90 mg tablet2.57USD tablet
Nifedipine er 90 mg tablet2.56USD tablet
Procardia xl 30 mg tablet2.56USD tablet
Procardia XL 30 mg 24 Hour tablet2.39USD tablet
NIFEdipine CR Osmotic 60 mg 24 Hour tablet2.38USD tablet
Nifedipine er 60 mg tablet2.29USD tablet
Afeditab cr 60 mg tablet2.24USD tablet
Nifediac cc 60 mg tablet2.17USD tablet
Adalat CC 30 mg 24 Hour tablet1.81USD tablet
NIFEdipine 20 mg capsule1.74USD capsule
Adalat cc 30 mg tablet1.61USD tablet
Adalat Xl 60 mg Extended-Release Tablet1.41USD tablet
NIFEdipine CR Osmotic 30 mg 24 Hour tablet1.35USD tablet
Adalat Xl 20 mg Extended-Release Tablet1.34USD tablet
Adalat Xl 30 mg Extended-Release Tablet1.34USD tablet
Nifedipine er 30 mg tablet1.32USD tablet
Afeditab cr 30 mg tablet1.26USD tablet
Mylan-Nifedipine Extended Release 60 mg Extended-Release Tablet1.18USD tablet
Procardia 10 mg capsule1.17USD capsule
Nifediac cc 30 mg tablet1.15USD tablet
NIFEdipine 10 mg capsule0.97USD capsule
Apo-Nifed 10 mg Capsule0.51USD capsule
Apo-Nifed 5 mg Capsule0.39USD capsule
Coral calcium plus 1500 mg caplet0.13USD caplet
Coral calcium 1000 mg caplet0.09USD caplet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5264446No1993-11-232010-11-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)172-174 °CPhysProp
water solubilityInsolubleNot Available
logP2.20MASUMOTO,K ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0177 mg/mLALOGPS
logP2.49ALOGPS
logP1.82ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)5.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.45 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity92.16 m3·mol-1ChemAxon
Polarizability33.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9073
Blood Brain Barrier-0.9536
Caco-2 permeable+0.7853
P-glycoprotein substrateNon-substrate0.5089
P-glycoprotein inhibitor IInhibitor0.8771
P-glycoprotein inhibitor IIInhibitor0.7902
Renal organic cation transporterNon-inhibitor0.9182
CYP450 2C9 substrateNon-substrate0.7776
CYP450 2D6 substrateNon-substrate0.5726
CYP450 3A4 substrateSubstrate0.705
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.6122
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.6715
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9013
Ames testNon AMES toxic0.6973
CarcinogenicityNon-carcinogens0.5412
BiodegradationNot ready biodegradable0.9675
Rat acute toxicity2.5425 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.863
hERG inhibition (predictor II)Non-inhibitor0.903
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
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/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0v4i-1691000000-c4842fe2c3070d6e90dd

Taxonomy

Description
This compound belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. These are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Hydropyridines
Direct Parent
Dihydropyridinecarboxylic acids and derivatives
Alternative Parents
Nitrobenzenes / Nitroaromatic compounds / Dicarboxylic acids and derivatives / Vinylogous amides / Enoate esters / Methyl esters / Amino acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Enamines
show 6 more
Substituents
Dihydropyridinecarboxylic acid derivative / Nitrobenzene / Nitroaromatic compound / Monocyclic benzene moiety / Dicarboxylic acid or derivatives / Benzenoid / Methyl ester / Enoate ester / Alpha,beta-unsaturated carboxylic ester / Vinylogous amide
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dihydropyridine (CHEBI:7565)

Targets

Kind
Protein
Organism
Human
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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. Striessnig, J. (2004). Ca 2+ channel blockers. In Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin: Springer. [ISBN:9783540298328]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-...
Gene Name
CACNA2D1
Uniprot ID
P54289
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-1
Molecular Weight
124566.93 Da
References
  1. Li GR, Deng XL, Sun H, Chung SS, Tse HF, Lau CP: Ion channels in mesenchymal stem cells from rat bone marrow. Stem Cells. 2006 Jun;24(6):1519-28. Epub 2006 Feb 16. [PubMed:16484345]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
The beta subunit of voltage-dependent calcium channels contributes to the function of the calcium channel by increasing peak calcium current, shifting the voltage dependencies of activation and ina...
Gene Name
CACNB2
Uniprot ID
Q08289
Uniprot Name
Voltage-dependent L-type calcium channel subunit beta-2
Molecular Weight
73579.925 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Striessnig, J. (2004). Ca 2+ channel blockers. In Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin: Springer. [ISBN:9783540298328]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity involved sa node cell action potential
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
CACNA1D
Uniprot ID
Q01668
Uniprot Name
Voltage-dependent L-type calcium channel subunit alpha-1D
Molecular Weight
245138.75 Da
References
  1. Bell DC, Butcher AJ, Berrow NS, Page KM, Brust PF, Nesterova A, Stauderman KA, Seabrook GR, Nurnberg B, Dolphin AC: Biophysical properties, pharmacology, and modulation of human, neuronal L-type (alpha(1D), Ca(V)1.3) voltage-dependent calcium currents. J Neurophysiol. 2001 Feb;85(2):816-27. [PubMed:11160515]
  2. Sinnegger-Brauns MJ, Huber IG, Koschak A, Wild C, Obermair GJ, Einzinger U, Hoda JC, Sartori SB, Striessnig J: Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms. Mol Pharmacol. 2009 Feb;75(2):407-14. doi: 10.1124/mol.108.049981. Epub 2008 Nov 24. [PubMed:19029287]
Kind
Protein
Organism
Human
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
CACNA1S
Uniprot ID
Q13698
Uniprot Name
Voltage-dependent L-type calcium channel subunit alpha-1S
Molecular Weight
212348.1 Da
References
  1. Peterson BZ, Catterall WA: Allosteric interactions required for high-affinity binding of dihydropyridine antagonists to Ca(V)1.1 Channels are modulated by calcium in the pore. Mol Pharmacol. 2006 Aug;70(2):667-75. Epub 2006 May 4. [PubMed:16675661]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 Da
References
  1. Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
Voltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain and the central nervous system, but also in the kidney (PubMed:1990381...
Gene Name
KCNA1
Uniprot ID
Q09470
Uniprot Name
Potassium voltage-gated channel subfamily A member 1
Molecular Weight
56465.01 Da
References
  1. Bett GC, Rasmusson RL: Modification of K+ channel-drug interactions by ancillary subunits. J Physiol. 2008 Feb 15;586(4):929-50. Epub 2007 Dec 20. [PubMed:18096604]
Kind
Protein
Organism
Human
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. Lee TS, Kaku T, Takebayashi S, Uchino T, Miyamoto S, Hadama T, Perez-Reyes E, Ono K: Actions of mibefradil, efonidipine and nifedipine block of recombinant T- and L-type Ca channels with distinct inhibitory mechanisms. Pharmacology. 2006;78(1):11-20. Epub 2006 Aug 7. [PubMed:16899990]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Krasowski MD, Ai N, Hagey LR, Kollitz EM, Kullman SW, Reschly EJ, Ekins S: The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species. BMC Biochem. 2011 Feb 3;12:5. doi: 10.1186/1471-2091-12-5. [PubMed:21291553]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. Foti RS, Rock DA, Wienkers LC, Wahlstrom JL: Selection of alternative CYP3A4 probe substrates for clinical drug interaction studies using in vitro data and in vivo simulation. Drug Metab Dispos. 2010 Jun;38(6):981-7. doi: 10.1124/dmd.110.032094. Epub 2010 Mar 4. [PubMed:20203109]
  2. Lee SJ, Bell DA, Coulter SJ, Ghanayem B, Goldstein JA: Recombinant CYP3A4*17 is defective in metabolizing the hypertensive drug nifedipine, and the CYP3A4*17 allele may occur on the same chromosome as CYP3A5*3, representing a new putative defective CYP3A haplotype. J Pharmacol Exp Ther. 2005 Apr;313(1):302-9. Epub 2005 Jan 5. [PubMed:15634941]
  3. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  5. Galetin A, Clarke SE, Houston JB: Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metab Dispos. 2002 Dec;30(12):1512-22. [PubMed:12433827]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Nicardipine FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drocourt L, Pascussi JM, Assenat E, Fabre JM, Maurel P, Vilarem MJ: Calcium channel modulators of the dihydropyridine family are human pregnane X receptor activators and inducers of CYP3A, CYP2B, and CYP2C in human hepatocytes. Drug Metab Dispos. 2001 Oct;29(10):1325-31. [PubMed:11560876]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
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. Teng S, Jekerle V, Piquette-Miller M: Induction of ABCC3 (MRP3) by pregnane X receptor activators. Drug Metab Dispos. 2003 Nov;31(11):1296-9. [PubMed:14570758]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [PubMed:11297522]
  2. Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. [PubMed:11231118]
  3. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742]
  4. Takara K, Sakaeda T, Tanigawara Y, Nishiguchi K, Ohmoto N, Horinouchi M, Komada F, Ohnishi N, Yokoyama T, Okumura K: Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression. Eur J Pharm Sci. 2002 Aug;16(3):159-65. [PubMed:12128170]
  5. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372]
  6. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
  7. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Payen L, Sparfel L, Courtois A, Vernhet L, Guillouzo A, Fardel O: The drug efflux pump MRP2: regulation of expression in physiopathological situations and by endogenous and exogenous compounds. Cell Biol Toxicol. 2002;18(4):221-33. [PubMed:12206135]
Kind
Protein
Organism
Human
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. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 13:32