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Details

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

Description

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

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Nifedipine prolongs a neuromuscular blockade caused by atracurium].
1992
Effect of different convulsants on calmodulin levels and proto-oncogene c-fos expression in the central nervous system.
1992 Aug
[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
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
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
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.
2003
Nifedipine inhibits apoptotic cell death of cultured endothelial cells induced by tumor necrosis factor-alpha.
2003
[Pathogenetic basis of the application of calcium antagonists in the treatment of recurrent peptic ulcer].
2003
Vasodilator agents protect against indinavir nephrotoxicity.
2003 Aug
[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
Protection of blood-brain barrier breakdown by nifedipine in adrenaline-induced acute hypertension.
2004 Apr
Sertoli cell modulates MAA-induced apoptosis of germ cells throughout voltage-operated calcium channels.
2004 Feb
The CACNA1F gene encodes an L-type calcium channel with unique biophysical properties and tissue distribution.
2004 Feb 18
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
Comparison of once-daily nifedipine controlled-release with twice-daily nifedipine retard in the treatment of essential hypertension.
2004 May
The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes.
2004 Nov
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
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
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
Ventricular arrhythmia following short-acting nifedipine administration.
2005 Jul
CYP3A4 substrate selection and substitution in the prediction of potential drug-drug interactions.
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

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 Mon Oct 21 20:07:32 UTC 2019
Edited
by admin
on Mon Oct 21 20:07:32 UTC 2019
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 [JAN]
Common Name English
NIFEDIPINE [USP-RS]
Common Name English
AFEDITAB CR
Brand Name English
NIFEDIPINE [EP]
Common 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
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 Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
FDA ORPHAN DRUG 57991
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
NDF-RT N0000000069
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
WHO-ATC C08GA01
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
WHO-VATC QC08CA55
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
LIVERTOX 684
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
NCI_THESAURUS C333
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
NDF-RT N0000007556
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
WHO-ATC C08CA55
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
WHO-ATC C08CA05
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
WHO-VATC QC08CA05
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 22.2
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
NDF-RT N0000175421
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
NIFEDIPINE
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
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 Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
ECHA (EC/EINECS)
244-598-3
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
INN
3222
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
LactMed
21829-25-4
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
EPA CompTox
21829-25-4
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
MESH
D009543
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
NCI_THESAURUS
C29290
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
MERCK INDEX
M7883
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY Merck Index
EVMPD
SUB09253MIG
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
HSDB
21829-25-4
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
CAS
21829-25-4
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
PUBCHEM
4485
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
RXCUI
7417
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY RxNorm
IUPHAR
2514
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
WIKIPEDIA
NIFEDIPINE
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
ChEMBL
CHEMBL193
Created by admin on Mon Oct 21 20:07:32 UTC 2019 , Edited by admin on Mon Oct 21 20:07:32 UTC 2019
PRIMARY
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