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

Details

Stereochemistry ACHIRAL
Molecular Formula C17H18N2O6
Molecular Weight 346.3346
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
2523
Curator's Comment: nifedipine can easily cross the blood-brain barrier in the rat

Originator

Approval Year

1981
136
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 2.0 µM [IC50]
Inhibitor
8228
 1.0 nM [Ki]
Inhibitor
8228
 37.5 µM [IC50]
Inhibitor
8228
 7.8 µM [IC50]
Target ID: Cholangiocarcinoma, Mz-ChA-1, human
Inhibitor
8228
 15.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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
8360
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
1709

inhibitor
1579

inducer
768
inhibitor
1752

inducer
383
inhibitor
1837
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Nav1.5
95

UGT2B7
146

OATP1B1
781

BCRP
691

P-gp
1437

CYP2C8
901

BSEP
401

CYP1A1
110

CYP1A2
1509

CYP2A6
704

CYP2B6
799

CYP2C19
1463

CYP2E1
876
CYP3A5
391

P-gp
1527
MRP3
54

CYP2B6
538
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
955
 moderate
CYP1A1
218
 no
CYP2A6
736
 no
CYP2B6
985
 no
CYP2C19
1537
 no
CYP2C9
1803
 no
CYP2D6
1875
 no
CYP3A4
1909
 no
UGT2B7
157
 weak [IC50 186 uM]
P-gp
1626
 weak [IC50 472 uM]
BCRP
765
 weak
CYP2E1
964
 weak
BSEP
402
 yes
CYP1A2
1673
 yes
CYP2B6
985
 yes
CYP2C9
1803
 yes
CYP3A4
1909
 yes
MRP3
208
 yes
OATP1B1
796
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1709
 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
391
 minor
P-gp
1527
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
98
hERG
1632
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
[Sexual impotence caused by nifedipine].
1992 Jan 18
The calcium channel antagonist nifedipine causes confusion when used to treat opiate withdrawal in morphine-dependent patients.
1992 Nov
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
Nifedipine-induced hypotensive shock.
1997 Dec
[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
Nifedipine improves endothelial function in hypercholesterolemia, independently of an effect on blood pressure or plasma lipids.
1999 Jun
Echocardiographic predictors of an adverse response to a nifedipine trial in primary pulmonary hypertension: diminished left ventricular size and leftward ventricular septal bowing.
1999 Nov
Effects of the antihypertensive drug nifedipine on albuminuria and renal histopathology in young spontaneously hypertensive rats with diabetes.
1999 Nov
A randomized, double-blind trial of oral nifedipine and intravenous labetalol in hypertensive emergencies of pregnancy.
1999 Oct
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
Life threatening coronary artery spasm in childhood Kimura's disease.
2000 Aug
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
Nifedipine and haemolytic anaemia.
2000 Feb
Impact of cyclosporin A pharmacokinetics on the presence of side effects in pediatric renal transplantation.
2000 Feb
Immunolocalizaiton of c-Myc and bcl-2 proto-oncogene products in gingival hyperplasia induced by nifedipine and phenytoin.
2000 Jan
Nifedipine-induced coronary vasodilation in ischemic hearts is attributable to bradykinin- and NO-dependent mechanisms in dogs.
2000 Jan 25
Morbidity and mortality in patients randomised to double-blind treatment with a long-acting calcium-channel blocker or diuretic in the International Nifedipine GITS study: Intervention as a Goal in Hypertension Treatment (INSIGHT).
2000 Jul 29
Characterization of nifedipine-resistant calcium current in neonatal rat ventricular cardiomyocytes.
2000 Nov
Keratinocyte growth factor is upregulated by the hyperplasia-inducing drug nifedipine.
2000 Oct
Effectiveness of nifedipine and deflazacort in the management of distal ureter stones.
2000 Oct 1
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
Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.
2001 Feb
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
Oxidative stress and TGFbeta in kidney-transplanted patients with cyclosporin-induced hypertension. Effect of carvedilol and nifedipine.
2002 Aug
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
Depression--an adverse event with nifedipine.
2002 Nov
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.
2003
[Pathogenetic basis of the application of calcium antagonists in the treatment of recurrent peptic ulcer].
2003
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
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
Comparison of once-daily nifedipine controlled-release with twice-daily nifedipine retard in the treatment of essential hypertension.
2004 May
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
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
CYP3A4 substrate selection and substitution in the prediction of potential drug-drug interactions.
2005 Jul
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
45
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 Thu Jul 06 23:17:47 UTC 2023
Edited
by admin
on Thu Jul 06 23:17:47 UTC 2023
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
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 Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
FDA ORPHAN DRUG 57991
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
NDF-RT N0000000069
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
WHO-ATC C08GA01
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
WHO-VATC QC08CA55
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
LIVERTOX NBK548324
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
NCI_THESAURUS C333
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
NDF-RT N0000007556
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
WHO-ATC C08CA55
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
WHO-ATC C08CA05
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
WHO-VATC QC08CA05
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 22.2
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
NDF-RT N0000175421
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
NIFEDIPINE
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
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 Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
244-598-3
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
INN
3222
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID2025715
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
MESH
D009543
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
NCI_THESAURUS
C29290
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
DAILYMED
I9ZF7L6G2L
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
CHEBI
7565
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
MERCK INDEX
M7883
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY Merck Index
FDA UNII
I9ZF7L6G2L
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
EVMPD
SUB09253MIG
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
HSDB
7775
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
CAS
21829-25-4
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
PUBCHEM
4485
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
RXCUI
7417
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY RxNorm
IUPHAR
2514
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
WIKIPEDIA
NIFEDIPINE
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL193
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
NSC
757242
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
DRUG CENTRAL
1922
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
LACTMED
Nifedipine
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
SMS_ID
100000090371
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1463508
Created by admin on Thu Jul 06 23:17:48 UTC 2023 , Edited by admin on Thu Jul 06 23:17:48 UTC 2023
PRIMARY
Related Record Type Details
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
Structure of DEHYDRONITROSONIFEDIPINE
DEGRADENT -> PARENT
LIGHT INDUCED DEGRADENT
CYTOCHROME P450 3A4
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 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 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
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