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Details

Stereochemistry ACHIRAL
Molecular Formula C17H18N2O6
Molecular Weight 346.3346
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Nifedipine

SMILES

COC(=O)C1=C(C)NC(C)=C(C1C2=C(C=CC=C2)[N+]([O-])=O)C(=O)OC

InChI

InChIKey=HYIMSNHJOBLJNT-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C17H18N2O6
Molecular Weight 346.3346
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020198s023lbl.pdf

Nifedipine has been formulated as both a long- and short-acting 1,4-dihydropyridine calcium channel blocker. Nifedipine is sold under the brand names Adalat and Procardia among others. 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. Nifedipine is used 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).

CNS Activity

CNS Penetrant
2588
Curator's Comment: nifedipine can easily cross the blood-brain barrier in the rat

Originator

Approval Year

1981
142
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 2.0 µM [IC50]
Inhibitor
8504
 1.0 nM [Ki]
Inhibitor
8504
 37.5 µM [IC50]
Inhibitor
8504
 7.8 µM [IC50]
Cholangiocarcinoma, Mz-ChA-1, human
2
Target ID: Cholangiocarcinoma, Mz-ChA-1, human
Inhibitor
8504
 15.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
PROCARDIA

Approved Use

I. Vasospastic Angina PROCARDIA (nifedipine) is indicated for the management of vasospastic angina confirmed by any of the following criteria: 1) classical pattern of angina at rest accompanied by ST segment elevation, 2) angina or coronary artery spasm provoked by ergonovine, or 3) angiographically demonstrated coronary artery spasm. In those patients who have had angiography, the presence of significant fixed obstructive disease is not incompatible with the diagnosis of vasospastic angina, provided that the above criteria are satisfied. PROCARDIA may also be used where the clinical presentation suggests a possible vasospastic component but where vasospasm has not been confirmed, e.g., where pain has a variable threshold on exertion or when angina is refractory to nitrates and/or adequate doses of beta blockers. II. Chronic Stable Angina (Classical Effort-Associated Angina) PROCARDIA is indicated for the management of chronic stable angina (effort-associated angina) without evidence of vasospasm in patients who remain symptomatic despite adequate doses of beta blockers and/or organic nitrates or who cannot tolerate those agents.

Launch Date

1981
Primary
Approved
8583
PROCARDIA

Approved Use

I. Vasospastic Angina PROCARDIA (nifedipine) is indicated for the management of vasospastic angina confirmed by any of the following criteria: 1) classical pattern of angina at rest accompanied by ST segment elevation, 2) angina or coronary artery spasm provoked by ergonovine, or 3) angiographically demonstrated coronary artery spasm. In those patients who have had angiography, the presence of significant fixed obstructive disease is not incompatible with the diagnosis of vasospastic angina, provided that the above criteria are satisfied. PROCARDIA may also be used where the clinical presentation suggests a possible vasospastic component but where vasospasm has not been confirmed, e.g., where pain has a variable threshold on exertion or when angina is refractory to nitrates and/or adequate doses of beta blockers. II. Chronic Stable Angina (Classical Effort-Associated Angina) PROCARDIA is indicated for the management of chronic stable angina (effort-associated angina) without evidence of vasospasm in patients who remain symptomatic despite adequate doses of beta blockers and/or organic nitrates or who cannot tolerate those agents.

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
78.5 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3609112/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIFEDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
148 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3609112/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIFEDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3609112/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIFEDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
8%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020198s023lbl.pdf
unknown
 NIFEDIPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
90 mg single, oral
Overdose
Dose: 90 mg
Route: oral
Route: single
Dose: 90 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
Disc. AE: Tachycardia, Hyperglycemia...
AEs leading to
discontinuation/dose reduction:
Tachycardia (grade 5, 1 patient)
Hyperglycemia (grade 5, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
Health Status: healthy
Age Group: 34 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
Disc. AE: Hypotension, Acidosis...
AEs leading to
discontinuation/dose reduction:
Hypotension (1 patient)
Acidosis (1 patient)
Hyperglycemia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
2400 mg single, oral
Overdose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
unknown, 37 years
Health Status: unknown
Age Group: 37 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
Disc. AE: Intestinal infarction...
AEs leading to
discontinuation/dose reduction:
Intestinal infarction (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3416517/
unknown, 54 years
Health Status: unknown
Age Group: 54 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3416517/
Disc. AE: Reflex tachycardia...
AEs leading to
discontinuation/dose reduction:
Reflex tachycardia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3416517/
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
unknown, 57 years
Health Status: unknown
Age Group: 57 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
Disc. AE: Hypotension, Tachycardia...
AEs leading to
discontinuation/dose reduction:
Hypotension (1 patient)
Tachycardia (1 patient)
Flushing (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
unhealthy, 59 years
Health Status: unhealthy
Age Group: 59 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
Disc. AE: Hypotension, Hyperglycemia...
AEs leading to
discontinuation/dose reduction:
Hypotension (grade 4, 1 patient)
Hyperglycemia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
180 mg 1 times / day steady, oral
Highest studied dose
Dose: 180 mg, 1 times / day
Route: oral
Route: steady
Dose: 180 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019684s023lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019684s023lbl.pdf
DLT: Edema...
Dose limiting toxicities:
Edema (30%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019684s023lbl.pdf
30 mg 1 times / day steady, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
unhealthy, mean 33.3 years
Health Status: unhealthy
Age Group: mean 33.3 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Vomiting (1 patient)
Headache (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
AEs

AEs

AESignificanceDosePopulation
Hyperglycemia grade 5, 1 patient
Disc. AE
90 mg single, oral
Overdose
Dose: 90 mg
Route: oral
Route: single
Dose: 90 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
Tachycardia grade 5, 1 patient
Disc. AE
90 mg single, oral
Overdose
Dose: 90 mg
Route: oral
Route: single
Dose: 90 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/17276811/
Acidosis 1 patient
Disc. AE
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
Health Status: healthy
Age Group: 34 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
Hyperglycemia 1 patient
Disc. AE
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
Health Status: healthy
Age Group: 34 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
Hypotension 1 patient
Disc. AE
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
Health Status: healthy
Age Group: 34 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
Intestinal infarction 1 patient
Disc. AE
2400 mg single, oral
Overdose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
unknown, 37 years
Health Status: unknown
Age Group: 37 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
Reflex tachycardia 1 patient
Disc. AE
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3416517/
unknown, 54 years
Health Status: unknown
Age Group: 54 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3416517/
Flushing 1 patient
Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
unknown, 57 years
Health Status: unknown
Age Group: 57 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
Hypotension 1 patient
Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
unknown, 57 years
Health Status: unknown
Age Group: 57 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
Tachycardia 1 patient
Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
unknown, 57 years
Health Status: unknown
Age Group: 57 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2261244/
Hyperglycemia 1 patient
Disc. AE
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
unhealthy, 59 years
Health Status: unhealthy
Age Group: 59 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
Hypotension grade 4, 1 patient
Disc. AE
900 mg single, oral
Overdose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
unhealthy, 59 years
Health Status: unhealthy
Age Group: 59 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/3740090/
Edema 30%
DLT
180 mg 1 times / day steady, oral
Highest studied dose
Dose: 180 mg, 1 times / day
Route: oral
Route: steady
Dose: 180 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019684s023lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019684s023lbl.pdf
Headache 1 patient
Disc. AE
30 mg 1 times / day steady, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
unhealthy, mean 33.3 years
Health Status: unhealthy
Age Group: mean 33.3 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
Nausea 1 patient
Disc. AE
30 mg 1 times / day steady, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
unhealthy, mean 33.3 years
Health Status: unhealthy
Age Group: mean 33.3 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
Vomiting 1 patient
Disc. AE
30 mg 1 times / day steady, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
unhealthy, mean 33.3 years
Health Status: unhealthy
Age Group: mean 33.3 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252

inducer
1087
inhibitor
2438

inducer
440
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Nav1.5
116

UGT2B7
197

OATP1B1
1079

BCRP
910

P-gp
1741

CYP2C8
1057

BSEP
550

CYP1A1
132

CYP1A2
2153

CYP2A6
879

CYP2B6
926

CYP2C19
2057

CYP2E1
1060
CYP3A5
446

P-gp
2052
MRP3
83

CYP2B6
669
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
1117
 moderate
CYP1A1
272
 no
CYP2A6
911
 no
CYP2B6
1160
 no
CYP2C19
2141
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP3A4
2633
 no
UGT2B7
210
 weak [IC50 186 uM]
P-gp
1932
 weak [IC50 472 uM]
BCRP
985
 weak
CYP2E1
1146
 weak
BSEP
554
 yes
CYP1A2
2333
 yes
CYP2B6
1160
 yes
CYP2C9
2497
 yes
CYP3A4
2633
 yes
MRP3
326
 yes
OATP1B1
1095
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 major
yes (co-administration study)
Comment: [ADALAT® XL®PRODUCT MONOGRAPH]: Use of ADALAT XL with drugs that result in strong inhibition of CYP 3A4, such as ketoconazole, clarithromycin, ritonavir, may lead to increased plasma levels of nifedipine and associated serious adverse events. Such concomitant use should be avoided.
CYP3A5
446
 minor
P-gp
2052
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
119
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7565
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7565
eMolecules
715726
https://www.emolecules.com/cgi-bin/more?vid=715726
MolPort
MolPort-000-787-707
https://www.molport.com/shop/molecule-link/MolPort-000-787-707
Selleck Chemicals
Nifedipine(Adalat)
http://www.selleckchem.com/products/Nifedipine(Adalat).html
ZINC
ZINC000085205448
http://zinc15.docking.org/substances/ZINC000085205448
PubMed

PubMed

TitleDatePubMed
[Nifedipine prolongs a neuromuscular blockade caused by atracurium].
1992
Nerve growth factor-stimulated calcium uptake into PC12 cells: uniqueness of the channel and evidence for phosphorylation.
1992 Apr
Effect of different convulsants on calmodulin levels and proto-oncogene c-fos expression in the central nervous system.
1992 Aug
[The effect of hypotensive nifedipine therapy on renal secretory function in hypertensive patients in the course of both compensated and non-compensated chronic renal failure].
1992 Dec 7-14
[Sexual impotence caused by nifedipine].
1992 Jan 18
A randomized prospective comparison of nifedipine and bed rest versus bed rest alone in the management of preeclampsia remote from term.
1992 Oct
Lindane-induced convulsions in NMRI and OF1 mice: antagonism with (+)MK-801 and voltage-dependent calcium channel blockers.
1992 Oct 16
Cortical blindness after nifedipine treatment.
1992 Sep 19
Adverse neurologic events associated with rebound hypertension after using short-acting nifedipine in childhood hypertension.
2001 Dec
Effect of acute blood pressure reduction on endothelial function in the brachial artery of patients with essential hypertension.
2001 Mar
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Influence of an abrupt increase in blood pressure on the blood-brain barrier permeability during acute hypertension and epileptic seizures.
2001 Sep
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes.
2001 Sep 14
The drug efflux pump MRP2: regulation of expression in physiopathological situations and by endogenous and exogenous compounds.
2002
Oxidative stress and TGFbeta in kidney-transplanted patients with cyclosporin-induced hypertension. Effect of carvedilol and nifedipine.
2002 Aug
Effect of an orally active Na+/H+ exchange inhibitor, SMP-300, on experimental angina and myocardial infarction models in rats.
2002 Feb
Nifedipine or hydralazine as a first-line agent to control hypertension in severe preeclampsia.
2002 Jan
Evaluation of the safety of short-acting nifedipine in children with hypertension.
2002 Jan
Nifedipine prevents apoptosis of endothelial cells induced by oxidized low-density lipoproteins.
2002 Jul
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter.
2002 Jun
Delirium caused by donepezil: a case study.
2002 Mar
Short- and long-term influences of heavy metals on anionic drug efflux from renal proximal tubule.
2002 May
Depression--an adverse event with nifedipine.
2002 Nov
Symptomatic orthostasis with extended-release nifedipine and protease inhibitors.
2002 Oct
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002 Oct
[Pathogenetic basis of the application of calcium antagonists in the treatment of recurrent peptic ulcer].
2003
[Drug induced anosmia with nifedipine].
2003 Aug 23
Requirement of calcium and phosphate ions in expression of sodium-dependent vitamin C transporter 2 and osteopontin in MC3T3-E1 osteoblastic cells.
2003 Jun 17
ETA receptor-mediated Ca2+ mobilisation in H9c2 cardiac cells.
2003 Mar 1
An in vitro bioassay for xenobiotics using the SXR-driven human CYP3A4/lacZ reporter gene.
2003 May-Jun
Inhibitory effects of carvedilol on calcium channels in vascular smooth muscle cells.
2003 Nov
Induction of ABCC3 (MRP3) by pregnane X receptor activators.
2003 Nov
Fatality from administration of labetalol and crushed extended-release nifedipine.
2003 Oct
Clinical review: the management of hypertensive crises.
2003 Oct
Sertoli cell modulates MAA-induced apoptosis of germ cells throughout voltage-operated calcium channels.
2004 Feb
Comparison of the effects of a 7-day period of non-compliance on blood pressure control using three different antihypertensive agents.
2004 Jul
Proliferation of cultured human gingival fibroblasts caused by isradipine, a dihydropyridine-derivative calcium antagonist.
2004 Jun 30
The effect of basic fibroblast growth factor on cell cycle in human gingival fibroblasts from nifedipine responder and non-responder.
2004 Mar
Adverse events associated with aggressive treatment of increased blood pressure.
2004 May
The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes.
2004 Nov
Effect of nifedipine on endothelial function in normotensive smokers: potential contribution of increase in circulating hepatocyte growth factor.
2004 Oct
The effect of PAMAM dendrimer generation size and surface functional group on the aqueous solubility of nifedipine.
2004 Oct 13
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.
2005 Apr
Examination of 209 drugs for inhibition of cytochrome P450 2C8.
2005 Jan
Ventricular arrhythmia following short-acting nifedipine administration.
2005 Jul
The effect of IL-1alpha and nifedipine on cell proliferation and DNA synthesis in cultured human gingival fibroblasts.
2005 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Isolation of CYP3A4 Inhibitors from the Black Cohosh (Cimicifuga racemosa).
2005 Jun
Nifedipine gastrointestinal therapeutic system--hypertension management to improve cardiovascular outcomes.
2005 Sep
Quantitative PCR assay for cytochromes P450 2B and 3A induction in rat precision-cut liver slices: correlation study with induction in vivo.
2005 Sep-Oct
Patents

Patents

JP2000256195A
2
JP2001517210A
4
JP2003508349A
46
JP2005535563A
67
JP2007503263A
18
JP2007505704A
20
JP2008534056A
8
JP2009120600A
2
JP4739217B2
51
JPH01238528A
2
JPH05306225A
2
JPH05959A
2
JPS5455714A
2
JPS5520720A
2
JPS5547615A
2
JPS56115726A
2
JPS5813511A
2
JPS61129140A
2
JPS62249920A
2

Sample Use Guides

In Vivo Use Guide
Therapy should be initiated with the 10 mg capsule. The starting dose is one 10 mg capsule, swallowed whole, 3 times/day. The usual effective dose range is 10–20 mg three times daily. Some patients, especially those with evidence of coronary artery spasm, respond only to higher doses, more frequent administration, or both. In such patients, doses of 20–30 mg three or four times daily may be effective. Doses above 120 mg daily are rarely necessary. More than 180 mg per day is not recommended.
Route of Administration: Oral
In Vitro Use Guide
About 50% of the Ca(v) current was blocked by 10 uM of the L-type channel blocker nifedipine in human induced pluripotent stem cell-derived neurons.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:53:19 GMT 2025
Edited
by admin
on Wed Apr 02 09:53:19 GMT 2025
Record UNII
I9ZF7L6G2L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Nifedipine
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INCI   INN   USAN  
Official Name English
ADALAT
Preferred Name English
Nifedipine [USP MONOGRAPH]
Common Name English
Nifedipine [USP-RS]
Common Name English
NSC-757242
Code English
AFEDITAB CR
Brand Name English
NIFEDIPINE SLOW RELEASE
Common Name English
Nifedipine [WHO-IP]
Common Name English
Nifedipinum [WHO-IP LATIN]
Common Name English
PROCARDIA
Brand Name English
Nifedipine [ORANGE BOOK]
Common Name English
Nifedipine [USAN]
Common Name English
Nifedipine [WHO-DD]
Common Name English
BAY A 1040
Code English
Nifedipine [VANDF]
Common Name English
Nifedipine [EP MONOGRAPH]
Common Name English
Nifedipine [USP IMPURITY]
Common Name English
Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate
Systematic Name English
BAY-A-1040
Code English
Nifedipine [MART.]
Common Name English
CORACTEN
Brand Name English
Nifedipine [INN]
Common Name English
Nifedipine [MI]
Common Name English
Nifedipine [HSDB]
Common Name English
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester
Common Name English
Nifedipine [JAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QC08GA01
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
FDA ORPHAN DRUG 57991
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
NDF-RT N0000000069
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
WHO-ATC C08GA01
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
WHO-VATC QC08CA55
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
LIVERTOX NBK548324
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
NCI_THESAURUS C333
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
NDF-RT N0000007556
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
WHO-ATC C08CA55
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
WHO-ATC C08CA05
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
WHO-VATC QC08CA05
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 22.2
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
NDF-RT N0000175421
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
NIFEDIPINE
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY Description. A yellow, crystalline powder.Solubility. Nifedipine is practically insoluble in water; freely soluble in acetone R; sparingly soluble in dehydrated ethanol R.Category. Cardiovascular drug; calcium-channel blocking agent.Storage. Nifedipine should be kept in a tightly closed container, protected from light.Additional information. CAUTION: Nifedipine decomposes on exposure to daylight, artificial light of certain wavelengths, andultraviolet light.Requirements: Nifedipine contains not less than 98.0% and not more than 102.0% of C17H18N2O6, calculated with reference to the driedsubstance.Note: Throughout the monograph perform the tests and the assay in the dark or under a suitable fluorescent light, using lowactinicglassware.
DRUG BANK
DB01115
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
244-598-3
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
INN
3222
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID2025715
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
MESH
D009543
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
NCI_THESAURUS
C29290
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
DAILYMED
I9ZF7L6G2L
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
CHEBI
7565
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
MERCK INDEX
m7883
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY Merck Index
FDA UNII
I9ZF7L6G2L
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
EVMPD
SUB09253MIG
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
HSDB
7775
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
CAS
21829-25-4
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
PUBCHEM
4485
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
RXCUI
7417
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY RxNorm
IUPHAR
2514
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
WIKIPEDIA
NIFEDIPINE
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL193
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
NSC
757242
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
DRUG CENTRAL
1922
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
LACTMED
Nifedipine
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
SMS_ID
100000090371
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
RS_ITEM_NUM
1463508
Created by admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
PRIMARY
Related Record Type Details
Voltage-dependent L-type calcium channel subunit alpha-1C (Rat)
TARGET -> INHIBITOR
BINDING
IC50
VOLTAGE-DEPENDENT L-TYPE CALCIUM CHANNEL SUBUNIT ALPHA-1S
TARGET -> INHIBITOR
VOLTAGE-DEPENDENT L-TYPE CALCIUM CHANNEL SUBUNIT ALPHA-1D
TARGET -> INHIBITOR
Structure of DEHYDRONIFEDIPINE
DEGRADENT -> PARENT
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
Structure of NIFEDIPINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of DEHYDRONITROSONIFEDIPINE
DEGRADENT -> PARENT
LIGHT INDUCED DEGRADENT
Related Record Type Details
Structure of DEHYDRONIFEDIPINE
METABOLITE -> PARENT
PLASMA
Structure of DESISOBUTYL NISOLDIPINE
METABOLITE -> PARENT
MAJOR
URINE
Structure of 1,4,5,7-TETRAHYDRO-2-METHYL-4-(2-NITROPHENYL)-5-OXO-FURO(3,4-B)PYRIDINE-3-CARBOXYLIC ACID, METHYL ESTER
METABOLITE -> PARENT
MINOR
URINE
Structure of DESMETHYL DEHYDRONIFEDIPINE
METABOLITE -> PARENT
PLASMA; URINE
Related Record Type Details
Structure of DEHYDRONIFEDIPINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DEHYDRONITROSONIFEDIPINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHYL 3-AMINO-2-BUTENOATE, (2E)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-nitroso-nifedipine
IMPURITY -> PARENT
Structure of BUTANOIC ACID, 2-((2-NITROPHENYL)METHYLENE)-3-OXO-, METHYL ESTER, (2Z)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of Nifedipine
ACTIVE MOIETY
Blocks L-type calcium channels
NIH
NCATS
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