Identification

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

Nifedipine, or BAY a 1040, is a first generation dihydropyridine L-type calcium channel blocker, similar to nicardipine.3,10,11,13 Nifedipine was developed by Bayer and first described in the literature, along with other dihydropyridines, in 1972.11,12 Since nifedipine's development, second and third generation dihydropyridines have been developed with slower onsets and longer durations of action.10 The most popular of the third generation dihydropyridines is amlodipine.10

Nifedipine was granted FDA approval on 31 December 1981.13

Structure
Thumb
Synonyms
  • 4-(2'-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsäuredimethylester
  • Nifedipine
  • Nifedipino
  • Nifedipinum
External IDs
BAY A 1040
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdalatCapsuleOralBayer1997-01-072005-07-27Canada
Adalat - Cap 10mgCapsuleOralBayer1982-12-312005-07-27Canada
Adalat Cap 10mgCapsuleOralMiles Canada Inc. Pharmaceutical Division1982-12-312000-08-01Canada
Adalat Cap 5mgCapsuleOralMiles Canada 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 coated60 mg/1OralSchering Corporation2011-02-282013-07-01Us
Adalat CCTablet, film coated60 mg/1OralBayer1993-04-212017-11-10Us50419 0702 05 nlmimage10 531929c9
Adalat CCTablet, film coated30 mg/1OralSchering Corporation2011-02-282013-07-01Us
Adalat CCTablet, film coated90 mg/1OralPhysicians Total Care, Inc.1994-07-112011-06-30Us
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
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
Afeditab CRTablet, film coated, extended release60 mg/1OralAphena Pharma Solutions Tennessee, Inc.2002-11-01Not applicableUs
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 release30 mg/1OralCarilion Materials Management2002-11-01Not applicableUs00591 3193 01 nlmimage10 6d46b6f5
Apo-nifed PaTablet, extended releaseOralApotex Corporation1995-12-312019-01-16Canada
Apo-nifed PaTablet, extended releaseOralApotex Corporation1995-12-312019-01-16Canada
Dom-nifedipineCapsuleOralDominion PharmacalNot applicableNot applicableCanada
Dom-nifedipineCapsuleOralDominion PharmacalNot applicableNot applicableCanada
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
Adalat XL PlusNifedipine (30 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet, delayed release; Tablet, extended releaseOralBayer2008-07-242014-07-18Canada
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
International/Other Brands
Adapine / Afeditab / Coracten / Nifecard / Nifecor / Nifedical / NifedicalXL / Nifedipres
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

Nifedipine capsules are indicated to treat vasospastic angina and chronic stable angina.13 Extended release tablets are indicated to treat vasospastic angina, chronic stable angina, and hypertension.14,15

Associated Conditions
Pharmacodynamics

Nifedipine is an inhibitor of L-type voltage gated calcium channels that reduces blood pressure and increases oxygen supply to the heart.1 Immediate release nifedipine's duration of action requires dosing 3 times daily.13 Nifedipine dosing is generally 10-120mg daily.13 Patients should be counselled regarding the risk of excessive hypotension, angina, and myocardial infarction.13

Mechanism of action

Nifedipine blocks voltage gated L-type calcium channels in vascular smooth muscle and myocardial cells.1 This blockage prevents the entry of calcium ions into cells during depolarization, reducing peripheral arterial vascular resistance and dilating coronary arteries.1 These actions reduce blood pressure and increase the supply of oxygen to the heart, alleviating angina.1

TargetActionsOrganism
AVoltage-dependent L-type calcium channel subunit alpha-1C
inhibitor
Humans
UNuclear receptor subfamily 1 group I member 2
agonist
Humans
UCalmodulin
inhibitor
Humans
AVoltage-dependent L-type calcium channel subunit alpha-1D
inhibitor
Humans
UVoltage-dependent L-type calcium channel subunit alpha-1S
inhibitor
Humans
AVoltage-dependent L-type calcium channel subunit beta-2
inhibitor
Humans
UPotassium voltage-gated channel subfamily D member 3
inhibitor
Humans
UVoltage-dependent T-type calcium channel
inhibitor
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

Sublingual dosing leads to a Cmax of 10ng/mL, with a Tmax of 50min, and an AUC of 25ng*h/mL.9 Oral dosing leads to a Cmax of 82ng/mL, with a Tmax of 28min, and an AUC of 152ng*h/mL.9

Nifedipine is a Biopharmaceutics Classification System Class II drug, meaning it has low solubility and high intestinal permeability.8 It is almost completely absorbed in the gastrointestinal tract but has a bioavilability of 45-68%, partly due to first pass metabolism.3,8

Volume of distribution

The steady state volume of distribution of nifedipine is 0.62-0.77L/kg and the volume of distribution of the central compartment is 0.25-0.29L/kg.3

Protein binding

Nifedipine is 92-98% protein bound in serum.13 Nifedipine is 97±12% bound in a 40g/L solution of pure albumin.2 Nifedipine is 51.4±5.9% protein bound in a 50mg/100mL solution of alpha-1-acid glycoprotein, and 75.5±3.5% protein bound in a 150mg/mL solution.2

Metabolism

Nifedipine is predominantly metabolized by CYP3A4.1,8,13,14,15 Nifedipine is predominantly metabolized to 2,6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid, and then further metabolized to 2-hydroxymethyl-pyridine carboxylic acid.6 Nifedipine is also minorly metabolized to dehydronifedipine.7

Route of elimination

Nifedipine is 60-80% recovered in the urine as inactive water soluble metabolites, and the rest is eliminated in the feces as metabolites.14

Half life

The terminal elimination half life of nifedipine is approximately 2 hours.3,8

Clearance

The total body clearance of nifedipine is 450-700mL/min.3

Toxicity

The oral LD50 in rats is 1022mg/kg and in mice is 202mg/kg.16

Patients experiencing an overdose may present with hypotension, sinus node dysfunction, atrioventricular node dysfunction, and reflex tachycardia.4,5 Overdose may be managed by monitoring cardiovascular and respiratory function; elevating extremities; and administering vasopressors, fluids, and calcium infusions.13

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

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 metabolism of (R)-warfarin can be increased when combined with Nifedipine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Nifedipine.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Nifedipine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Nifedipine is combined with 2,4-thiazolidinedione.
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-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Nifedipine.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Nifedipine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Nifedipine.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Nifedipine.
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

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid excessive or chronic alcohol consumption.
  • Avoid grapefruit products. 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.
  • Avoid natural licorice.
  • Take with or without food.

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. Khan KM, Patel J, Schaefer TJ: Nifedipine . [PubMed:30725737]
  2. Otto J, Lesko LJ: Protein binding of nifedipine. J Pharm Pharmacol. 1986 May;38(5):399-400. doi: 10.1111/j.2042-7158.1986.tb04598.x. [PubMed:2872322]
  3. Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. [PubMed:3503594]
  4. Herrington DM, Insley BM, Weinmann GG: Nifedipine overdose. Am J Med. 1986 Aug;81(2):344-6. doi: 10.1016/0002-9343(86)90276-7. [PubMed:3740090]
  5. Whitebloom D, Fitzharris J: Nifedipine overdose. Clin Cardiol. 1988 Jul;11(7):505-6. doi: 10.1002/clc.4960110714. [PubMed:3416517]
  6. Raemsch KD, Sommer J: Pharmacokinetics and metabolism of nifedipine. Hypertension. 1983 Jul-Aug;5(4 Pt 2):II18-24. doi: 10.1161/01.hyp.5.4_pt_2.ii18. [PubMed:6862586]
  7. Waller DG, Renwick AG, Gruchy BS, George CF: The first pass metabolism of nifedipine in man. Br J Clin Pharmacol. 1984 Dec;18(6):951-4. doi: 10.1111/j.1365-2125.1984.tb02569.x. [PubMed:6529535]
  8. Nader AM, Quinney SK, Fadda HM, Foster DR: Effect of Gastric Fluid Volume on the In Vitro Dissolution and In Vivo Absorption of BCS Class II Drugs: a Case Study with Nifedipine. AAPS J. 2016 Jul;18(4):981-8. doi: 10.1208/s12248-016-9918-x. Epub 2016 Apr 22. [PubMed:27106837]
  9. van Harten J, Burggraaf K, Danhof M, van Brummelen P, Breimer DD: Negligible sublingual absorption of nifedipine. Lancet. 1987 Dec 12;2(8572):1363-5. doi: 10.1016/s0140-6736(87)91258-x. [PubMed:2890954]
  10. Wang AL, Iadecola C, Wang G: New generations of dihydropyridines for treatment of hypertension. J Geriatr Cardiol. 2017 Jan;14(1):67-72. doi: 10.11909/j.issn.1671-5411.2017.01.006. [PubMed:28270844]
  11. Godfraind T: Discovery and Development of Calcium Channel Blockers. Front Pharmacol. 2017 May 29;8:286. doi: 10.3389/fphar.2017.00286. eCollection 2017. [PubMed:28611661]
  12. Vater W, Kroneberg G, Hoffmeister F, Saller H, Meng K, Oberdorf A, Puls W, Schlossmann K, Stoepel K: [Pharmacology of 4-(2'-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (Nifedipine, BAY a 1040)]. Arzneimittelforschung. 1972 Jan;22(1):1-14. [PubMed:4622472]
  13. FDA Approved Drug Products: Procardia Nifedipine Oral Capsules [Link]
  14. FDA Approved Drug Products: Procardia XL Nifedipine Oral Extended Release Tablets [Link]
  15. FDA Approved Drug Products: Adalat CC Nifedipine Oral Extended Release Tablets [Link]
  16. Cayman Chemical: Nifedipine MSDS [Link]
External Links
Human Metabolome Database
HMDB0015247
KEGG Drug
D00437
KEGG Compound
C07266
PubChem Compound
4485
PubChem Substance
46505103
ChemSpider
4330
BindingDB
50101817
RxNav
7417
ChEBI
7565
ChEMBL
CHEMBL193
ZINC
ZINC000085205448
Therapeutic Targets Database
DAP000529
PharmGKB
PA450631
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
C5U
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nifedipine
ATC Codes
C08CA55 — Nifedipine, combinationsC08GA01 — Nifedipine and diureticsC08CA05 — NifedipineC07FB03 — Atenolol and nifedipine
AHFS Codes
  • 24:28.08 — Dihydropyridines
PDB Entries
6jp5
FDA label
Download (206 KB)
MSDS
Download (74.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentDermatomyositis / Raynaud Phenomenon Due to Trauma / Raynaud's Phenomenon / System; Sclerosis / Systemic Lupus Erythematosus (SLE) / 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
1CompletedBasic ScienceOpioid Dependence1
1CompletedBasic ScienceSubstance, Addiction1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentAcute iron intoxication / Hemochromatosis / Thalassaemic disorders1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentHypertension,Essential1
1RecruitingTreatmentCytochrome P450 Interaction1
1, 2CompletedNot AvailableAnal Resting Pressure1
1, 2CompletedTreatmentChronic Anal Fissures1
1, 2CompletedTreatmentCongenital Adrenal Hyperplasia (CAH)1
1, 2CompletedTreatmentObstetric Labour, Premature1
1, 2TerminatedTreatmentAnal Fissures1
1, 2WithdrawnTreatmentHigh Blood Pressure (Hypertension) / Pregnancy Toxemias / Proteinuria1
2CompletedTreatmentAging / Cognitive Impairments / High Blood Pressure (Hypertension)1
2CompletedTreatmentChronic Kidney Disease (CKD) / CRD1
2CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentPlacenta Previa1
2CompletedTreatmentPremature Labour1
2Not Yet RecruitingTreatmentEpilepsies / Epilepsy, Localization Related1
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 Heart Disease / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia1
3CompletedTreatmentCardiovascular Heart Disease / Heart Diseases / Raynaud's Phenomenon / Vascular Diseases1
3CompletedTreatmentHigh Blood Pressure (Hypertension)4
3CompletedTreatmentPremature Labour1
3CompletedTreatmentPulmonary Hypertension (PH)1
3CompletedTreatmentVestibulitis / Vestibulodynia / Vulvar Diseases / Vulvar Pain / Vulvodynia1
3Not Yet RecruitingTreatmentLabor Preterm Multiple1
3Not Yet RecruitingTreatmentPostnatal Hypertension1
3RecruitingTreatmentPreterm Premature Rupture of Membranes1
3TerminatedTreatmentPremature Labour1
3Unknown StatusTreatmentKidney Stones1
3Unknown StatusTreatmentObstetric Labour, Premature1
3WithdrawnTreatmentDiabetic Nephropathies / High Blood Pressure (Hypertension)1
3WithdrawnTreatmentHigh Blood Pressure (Hypertension)1
3WithdrawnTreatmentPreterm Delivery1
3WithdrawnTreatmentThreatened Preterm Labor1
4Active Not RecruitingPreventionMountain Sickness1
4Active Not RecruitingTreatmentDiabetes / Hypertensive Disease1
4Active Not RecruitingTreatmentDrug Transporter1
4Active Not RecruitingTreatmentHigh Blood Pressure (Hypertension) / High Blood Pressure Variability1
4CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
4CompletedBasic SciencePremature Births1
4CompletedPreventionAtrial Fibrillation (AF)1
4CompletedPreventionChronic Renal Failure (CRF) / Coronary Artery Disease1
4CompletedPreventionHigh Blood Pressure (Hypertension)1
4CompletedPreventionPremature Births1
4CompletedSupportive CareManaging Preterm Labor1
4CompletedTreatmentHigh Blood Pressure (Hypertension)7
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Other and unspecified effects of high altitude1
4CompletedTreatmentHypertension in Pregnancy / Preeclampsia2
4CompletedTreatmentHypertension,Essential1
4CompletedTreatmentPremature Labour1
4RecruitingPreventionHypertension, Pregnancy-Induced / Prophylaxis of preeclampsia1
4RecruitingTreatmentGestational Hypertension / Hypertension in Pregnancy / Postpartum / Postpartum Preeclampsia / Severe Preeclampsia1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)3
4RecruitingTreatmentHypertension in Postpartum / Hypertension in Pregnancy1
4RecruitingTreatmentPremature Labour2
4Unknown StatusNot AvailableHypertension on Chronic Maintenance Hemodialysis1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension)1
4Unknown StatusTreatmentHypertension,Essential1
4Unknown StatusTreatmentUrinary Tract Stones1
Not AvailableActive Not RecruitingNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableActive Not RecruitingBasic ScienceEndothelium, Vascular1
Not AvailableActive Not RecruitingTreatmentDiastolic Heart Failure1
Not AvailableActive Not RecruitingTreatmentObstetric Labour, Premature1
Not AvailableCompletedNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiety / Anxiolysis / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Bradycardia / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest (CA) / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infection / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Dysrhythmia, Cardiac / Early-onset Schizophrenia Spectrum Disorders / Edema / Endocarditis / Epilepsies / Fibrinolytic Bleeding / Flu caused by Influenza / Gastroparesis / Gram-negative Infection / Gynaecological infection / Headache / Heart Failure / Heavy Menstrual Bleeding / Hemophilia / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hyperaldosteronism / Hyperlipidemias / Hypokalemia / Hypotension / Infantile Hemangiomas / Infection / Infection caused by staphylococci / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Insomnia / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Methicillin Resistant Staphylococcus Aureus (MRSA) / Migraine / Muscle Spasms / Nausea / Neuromuscular Blockade / Neutropenia / Nosocomial Pneumonia / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenia / Sedation / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and skin-structure infections / Skin and Subcutaneous Tissue Bacterial Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infection / Vomiting / Withdrawal1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)2
Not AvailableCompletedNot AvailablePremature Labour1
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 AvailableNot Yet RecruitingNot AvailableAdrenal Insufficiency / Arrhythmia / Asthma in Children / Chronic Lung Disease of Prematurity / Control of Serum Phosphorus / Edematous Conditions / Fibrinolysis; Hemorrhage / Heart Failure / Hemophilia Prior to Tooth Extraction / High Blood Pressure (Hypertension) / Hypermenorrhea / Hypertension, Resistant to Conventional Therapy / Hypokalemia / Insomnia / Pain / Pneumonia / Primary Hyperaldosteronism / Pulmonary Arterial Hypertension (PAH) / Skin-structure infections / Urinary Tract Infections in Children1
Not AvailableNot Yet RecruitingTreatmentContinuous Positive Airway Pressure (CPAP) / High Altitude Pulmonary Edema1
Not AvailableNot Yet RecruitingTreatmentArterial hypoxia / High Altitude Pulmonary Edema / Non-invasive Positive Pressure Ventilation1
Not AvailableNot Yet RecruitingTreatmentHypertension in Pregnancy / Preeclampsia1
Not AvailableRecruitingNot AvailableChronic Kidney Disease (CKD)1
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
TabletOral
Tablet, extended releaseOral
Kit; tablet, delayed release; tablet, extended releaseOral
Tablet, film coated, extended releaseOral90 mg/1
CapsuleOral10 mg
CapsuleOral10 mg/1
CapsuleOral20 mg/1
CapsuleOral5 mg
Capsule, liquid filledOral10 mg/1
Capsule, liquid filledOral20 mg/1
PowderNot applicable1 g/1g
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 releaseOral20 mg
Tablet, extended releaseOral30 mg
Tablet, extended releaseOral60 mg
Tablet, extended releaseOral90 mg/1
CapsuleOral
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
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
PropertyValueSource
melting point (°C)172-174 °CPhysProp
water solubilityInsolubleFDA Label
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
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. 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. 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]
  4. Striessnig, J. (2004). Ca 2+ channel blockers. In Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin: Springer. [ISBN:9783540298328]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
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]
Kind
Protein
Organism
Humans
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
Humans
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
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
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
Humans
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, 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]
  3. Striessnig, J. (2004). Ca 2+ channel blockers. In Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin: Springer. [ISBN:9783540298328]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Pore-forming (alpha) subunit of voltage-gated rapidly inactivating A-type potassium channels. May contribute to I(To) current in heart and I(Sa) current in neurons. Channel properties are modulated...
Gene Name
KCND3
Uniprot ID
Q9UK17
Uniprot Name
Potassium voltage-gated channel subfamily D member 3
Molecular Weight
73450.53 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 group
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...

Components:
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]
  2. Godfraind T: Discovery and Development of Calcium Channel Blockers. Front Pharmacol. 2017 May 29;8:286. doi: 10.3389/fphar.2017.00286. eCollection 2017. [PubMed:28611661]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
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. 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]
  5. Ramachandran SD, Vivares A, Klieber S, Hewitt NJ, Muenst B, Heinz S, Walles H, Braspenning J: Applicability of second-generation upcyte(R) human hepatocytes for use in CYP inhibition and induction studies. Pharmacol Res Perspect. 2015 Oct;3(5):e00161. doi: 10.1002/prp2.161. Epub 2015 Aug 10. [PubMed:26516577]
  6. Patki KC, Von Moltke LL, Greenblatt DJ: In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44. [PubMed:12814972]
  7. Flockhart Table of Drug Interactions [Link]
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. Ma B, Prueksaritanont T, Lin JH: Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30. [PubMed:10640508]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Katoh M, Nakajima M, Shimada N, Yamazaki H, Yokoi T: Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52. [PubMed:10805063]
  2. Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [PubMed:8474022]
  3. ADALAT® XL® (Nifedipine extended-release tablets) Product Monograph [Link]
Kind
Protein
Organism
Humans
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
References
  1. ADALAT® XL® (Nifedipine extended-release tablets) Product Monograph [Link]
Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
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. Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [PubMed:8474022]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
One in vitro study indicates that nifedipine induces CYP2B6 while another indicates that it does not demonstrate any induction of this enzyme. Clinical correlation of this enzyme action is known.
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. 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]
  2. Ramachandran SD, Vivares A, Klieber S, Hewitt NJ, Muenst B, Heinz S, Walles H, Braspenning J: Applicability of second-generation upcyte(R) human hepatocytes for use in CYP inhibition and induction studies. Pharmacol Res Perspect. 2015 Oct;3(5):e00161. doi: 10.1002/prp2.161. Epub 2015 Aug 10. [PubMed:26516577]
Kind
Protein
Organism
Humans
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. Katoh M, Nakajima M, Shimada N, Yamazaki H, Yokoi T: Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52. [PubMed:10805063]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Ma B, Prueksaritanont T, Lin JH: Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30. [PubMed:10640508]
  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]
Kind
Protein
Organism
Humans
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. Patki KC, Von Moltke LL, Greenblatt DJ: In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44. [PubMed:12814972]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
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. Otto J, Lesko LJ: Protein binding of nifedipine. J Pharm Pharmacol. 1986 May;38(5):399-400. doi: 10.1111/j.2042-7158.1986.tb04598.x. [PubMed:2872322]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
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...

Components:
References
  1. Otto J, Lesko LJ: Protein binding of nifedipine. J Pharm Pharmacol. 1986 May;38(5):399-400. doi: 10.1111/j.2042-7158.1986.tb04598.x. [PubMed:2872322]

Transporters

Kind
Protein
Organism
Humans
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]
Details
2. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. 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]
  2. 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]
Kind
Protein
Organism
Humans
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
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. 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
Humans
Pharmacological action
No
Actions
Inhibitor
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]
  2. Stieger B: Role of the bile salt export pump, BSEP, in acquired forms of cholestasis. Drug Metab Rev. 2010 Aug;42(3):437-45. doi: 10.3109/03602530903492004. [PubMed:20028269]

Drug created on June 13, 2005 07:24 / Updated on March 27, 2020 16:57

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