U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H18N2O6
Molecular Weight 346.3353
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIFEDIPINE

SMILES

CC1=C(C(c2ccccc2N(=O)=O)C(=C(C)N1)C(=O)OC)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 346.3353
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
2409
Curator's Comment:: nifedipine can easily cross the blood-brain barrier in the rat

Originator

Approval Year

1981
107
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7687
 2.0 µM [IC50]
Inhibitor
7687
 1.0 nM [Ki]
Inhibitor
7687
 37.5 µM [IC50]
Inhibitor
7687
 7.8 µM [IC50]
Target ID: Cholangiocarcinoma, Mz-ChA-1, human
Inhibitor
7687
 15.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
7968
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

3.78518405E11
Primary
Approved
7968
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

3.78518405E11
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
n = 1
Health Status: healthy
Age Group: 2 years
Sex: M
Population Size: 1
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
Co-administed with::
ethanol
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 34 years
Sex: F
Population Size: 1
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
Co-administed with::
ethanol
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
unknown, 37 years
n = 1
Health Status: unknown
Age Group: 37 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unknown
Condition: attempt to commit suicide
Age Group: 54 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unknown
Age Group: 57 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: with a history of angina, left bundle branch block, and depression
Age Group: 59 years
Sex: M
Population Size: 1
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
n = 1000
Health Status: unhealthy
Condition: hypertension and angina
Age Group: adult
Sex: unknown
Population Size: 1000
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
n = 25
Health Status: unhealthy
Condition: delivered at ≥32 weeks' gestation with persistent postpartum hypertension
Age Group: mean 33.3 years
Sex: F
Population Size: 25
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
n = 1
Health Status: healthy
Age Group: 2 years
Sex: M
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: 2 years
Sex: M
Population Size: 1
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
Co-administed with::
ethanol
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 34 years
Sex: F
Population Size: 1
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
Co-administed with::
ethanol
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 34 years
Sex: F
Population Size: 1
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
Co-administed with::
ethanol
Sources:
https://pubmed.ncbi.nlm.nih.gov/2362118/
healthy, 34 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 34 years
Sex: F
Population Size: 1
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
Co-administed with::
ethanol
Sources:
https://pubmed.ncbi.nlm.nih.gov/8523502/
unknown, 37 years
n = 1
Health Status: unknown
Age Group: 37 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unknown
Condition: attempt to commit suicide
Age Group: 54 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unknown
Age Group: 57 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unknown
Age Group: 57 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unknown
Age Group: 57 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: with a history of angina, left bundle branch block, and depression
Age Group: 59 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: with a history of angina, left bundle branch block, and depression
Age Group: 59 years
Sex: M
Population Size: 1
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
n = 1000
Health Status: unhealthy
Condition: hypertension and angina
Age Group: adult
Sex: unknown
Population Size: 1000
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
n = 25
Health Status: unhealthy
Condition: delivered at ≥32 weeks' gestation with persistent postpartum hypertension
Age Group: mean 33.3 years
Sex: F
Population Size: 25
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
n = 25
Health Status: unhealthy
Condition: delivered at ≥32 weeks' gestation with persistent postpartum hypertension
Age Group: mean 33.3 years
Sex: F
Population Size: 25
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
n = 25
Health Status: unhealthy
Condition: delivered at ≥32 weeks' gestation with persistent postpartum hypertension
Age Group: mean 33.3 years
Sex: F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/27786578/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1469

inhibitor
1171

inducer
657
inhibitor
1318

inducer
343
inhibitor
1421
inhibitor
1359

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Nav1.5
89

UGT2B7
130

OATP1B1
698

BCRP
574

P-gp
1087

CYP2C8
761

BSEP
363

CYP1A1
89

CYP1A2
1268

CYP2A6
594

CYP2B6
679

CYP2C19
1215

CYP2E1
761
CYP3A5
346

P-gp
1222
MRP3
55

CYP2B6
486
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
810
 moderate
CYP1A1
188
 no
CYP2A6
625
 no
CYP2B6
845
 no
CYP2C19
1277
 no
CYP2C9
1362
 no
CYP2D6
1455
 no
CYP3A4
1461
 no
UGT2B7
138
 weak [IC50 186 uM]
P-gp
1253
 weak [IC50 472 uM]
BCRP
639
 weak
CYP2E1
841
 weak
BSEP
364
 yes
CYP1A2
1406
 yes
CYP2B6
845
 yes
CYP2C9
1362
 yes
CYP3A4
1461
 yes
MRP3
200
 yes
OATP1B1
713
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1469
 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
346
 minor
P-gp
1222
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
91
hERG
1391
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7565
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7565
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
eMolecules
715726
https://www.emolecules.com/cgi-bin/more?vid=715726
PubMed

PubMed

TitleDatePubMed
[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
Lindane-induced convulsions in NMRI and OF1 mice: antagonism with (+)MK-801 and voltage-dependent calcium channel blockers.
1992 Oct 16
Hypotension and coronary events on nifedipine: reassessing nifedipine safety.
1998 Jun
[The effect of amlodipine, nifedipine and perindopril on insulin sensitivity and blood lipid of patients with essential hypertension].
1998 Mar
The influence of nifedipine on blood-brain barrier permeability during bicuculline-induced seizures.
1999 Aug
Reduced bcl-2 concentrations in hypertensive patients after lisinopril or nifedipine administration.
1999 Jan
Statins and peripheral neuropathy.
1999 Jan
Comparison between isosorbide dinitrate aerosol and nifedipine in the treatment of hypertensive emergencies.
1999 Jul
Ambulatory blood pressure profiles in essential hypertensives after treatment with a new once daily nifedipine formulation.
1999 Mar
[Effects of benidipine hydrochloride (Coniel) on blood pressure, heart rate and plasma norepinephrine concentration in spontaneously hypertensive rats].
1999 May
Sublingual nifedipine in elderly patients: even a low dose induces myocardial ischaemia.
1999 May-Jun
A randomized, double-blind trial of oral nifedipine and intravenous labetalol in hypertensive emergencies of pregnancy.
1999 Oct
Acute hypotensive, natriuretic, and hormonal effects of nifedipine in salt-sensitive and salt-resistant black normotensive and hypertensive subjects.
1999 Sep
Effects of a slow-release nifedipine on 24-hour ambulatory blood pressure and ischemic changes on 24-hour ambulatory electrocardiogram in patients with severe coronary artery disease.
2000
Evaluation of treatment efficacy of Raynaud phenomenon by digital blood pressure response to cooling. Raynaud's Treatment Study Investigators.
2000
[Effects of calcium antagonists on atherosclerosis progression and intima media thickness].
2000
D2 dopamine receptors in striatal medium spiny neurons reduce L-type Ca2+ currents and excitability via a novel PLC[beta]1-IP3-calcineurin-signaling cascade.
2000 Dec 15
Antiproteinuric effect of calcium antagonists on puromycin-induced experimental nephrosis.
2000 Jan
Nifedipine-induced coronary vasodilation in ischemic hearts is attributable to bradykinin- and NO-dependent mechanisms in dogs.
2000 Jan 25
Losartan: a review of its use, with special focus on elderly patients.
2000 Mar
Cardiovascular effects of melatonin in hypertensive patients well controlled by nifedipine: a 24-hour study.
2000 May
Stroke precipitated by moderate blood pressure reduction.
2000 Nov
Keratinocyte growth factor is upregulated by the hyperplasia-inducing drug nifedipine.
2000 Oct
Adverse neurologic events associated with rebound hypertension after using short-acting nifedipine in childhood hypertension.
2001 Dec
Comparative effects of amlodipine and nifedipine GITS during treatment and after missing two doses.
2001 Feb
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
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
Evaluation of the safety of short-acting nifedipine in children with hypertension.
2002 Jan
[Drug induced anosmia with nifedipine].
2003 Aug 23
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
Fatality from administration of labetalol and crushed extended-release nifedipine.
2003 Oct
Clinical review: the management of hypertensive crises.
2003 Oct
Proliferation of cultured human gingival fibroblasts caused by isradipine, a dihydropyridine-derivative calcium antagonist.
2004 Jun 30
Adverse events associated with aggressive treatment of increased blood pressure.
2004 May
Xenoestrogens at picomolar to nanomolar concentrations trigger membrane estrogen receptor-alpha-mediated Ca2+ fluxes and prolactin release in GH3/B6 pituitary tumor cells.
2005 Apr
Grapefruit juice-nifedipine interaction: possible involvement of several mechanisms.
2005 Apr
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
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
43
JP2005535563A
66
JP2007503263A
16
JP2007505704A
18
JP2008534056A
8
JP2009120600A
2
JP4739217B2
37
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 Fri Jun 25 21:02:57 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:57 UTC 2021
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  
INN   USAN  
Official Name English
NIFEDIPINE [USP MONOGRAPH]
Common Name English
NIFEDIPINE [USP-RS]
Common Name English
NSC-757242
Code English
NIFEDIPINE [INCI]
Common Name English
AFEDITAB CR
Brand Name English
NIFEDIPINE SLOW RELEASE
Common Name English
ADALAT
Brand 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
BAY A 1040
Code English
NIFEDIPINE [VANDF]
Common Name English
NIFEDIPINE [EP MONOGRAPH]
Common 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 [WHO-DD]
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 [USP]
Common Name English
Classification Tree Code System Code
WHO-VATC QC08GA01
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
FDA ORPHAN DRUG 57991
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
NDF-RT N0000000069
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
WHO-ATC C08GA01
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
WHO-VATC QC08CA55
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
LIVERTOX 684
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
NCI_THESAURUS C333
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
NDF-RT N0000007556
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
WHO-ATC C08CA55
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
WHO-ATC C08CA05
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
WHO-VATC QC08CA05
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 22.2
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
NDF-RT N0000175421
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
NIFEDIPINE
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
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 Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
244-598-3
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
INN
3222
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
EPA CompTox
21829-25-4
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
MESH
D009543
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
NCI_THESAURUS
C29290
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
MERCK INDEX
M7883
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY Merck Index
FDA UNII
I9ZF7L6G2L
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
EVMPD
SUB09253MIG
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
HSDB
7775
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
CAS
21829-25-4
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
PUBCHEM
4485
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
RXCUI
7417
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY RxNorm
IUPHAR
2514
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
WIKIPEDIA
NIFEDIPINE
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL193
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
DRUG CENTRAL
1922
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
LACTMED
Nifedipine
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY
USP_CATALOG
1463508
Created by admin on Fri Jun 25 21:02:57 UTC 2021 , Edited by admin on Fri Jun 25 21:02:57 UTC 2021
PRIMARY USP-RS
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
VOLTAGE-DEPENDENT L-TYPE CALCIUM CHANNEL SUBUNIT ALPHA-1D
TARGET -> INHIBITOR
Structure of DEHYDRONIFEDIPINE
DEGRADENT -> PARENT
Structure of NIFEDIPINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
DEHYDRONITROSONIFEDIPINE
DEGRADENT -> PARENT
LIGHT INDUCED DEGRADENT
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
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 NIFEDIPINE
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