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Details

Stereochemistry RACEMIC
Molecular Formula C18H20N2O6
Molecular Weight 360.3612
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITRENDIPINE

SMILES

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

InChI

InChIKey=PVHUJELLJLJGLN-UHFFFAOYSA-N
InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68009568

Nitrendipine is a calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive. By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, nitrendipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes. The decrease in intracellular calcium inhibits the contractile processes of the myocardial 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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.9 µM [Kd]
Blocker
537
 0.97 nM [IC50]
Blocker
537
 1.08 nM [IC50]
Blocker
537
 3.59 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Nitrendipine

Approved Use

Nitrendipine is used to treat mild to moderate hypertension.
PubMed

PubMed

TitleDatePubMed
Systemic and regional hemodynamics in normotensive and spontaneously hypertensive rats after slow-channel calcium blocker nitrendipine.
1984
Mode of antihypertensive action of nitrendipine.
1984
Clinical and systemic hemodynamic effects of nitrendipine.
1984 Jun
Nitrendipine block of cardiac calcium channels: high-affinity binding to the inactivated state.
1984 Oct
Antihypertensive treatment using calcium antagonists in combination with captopril rather than diuretics.
1985
The protective effect of nitrendipine on gentamicin acute renal failure in rats.
1985 Aug
Predictors of blood pressure increases after withdrawal of antihypertensive therapy.
1985 Dec
Relative potency of a beta-blocking and a calcium entry blocking agent as antihypertensive drugs in black patients.
1986
Renal effects of 1,4-dihydropyridines in animal models of hypertension and renal failure.
1987
Nitrendipine-stimulated release of prostacyclin-like substance in normal and atherosclerotic animals.
1987 Apr
Effects of nitrendipine and cilazapril alone or in combination on hemodynamics and regional blood flows in conscious spontaneously hypertensive rats.
1988
Calcium currents in embryonic and neonatal mammalian skeletal muscle.
1988 Jun
Cosecretion of calcitonin and calcitonin gene-related peptide from cultured rat medullary thyroid C cells.
1989 Feb
Treatment of hypertension in the elderly with a new calcium channel blocking drug, nitrendipine.
1989 Jan
Cocaine-induced small vessel spasm in isolated rat hearts.
1989 Jul
Nitrendipine versus hydrochlorothiazide in hypertensive patients over 70 years of age.
1989 Mar
[The effect of calcium antagonist nitrendipine on the morphological picture of experimentally-produced myocardial injuries in rats].
1990
Effects of nitrendipine and atenolol on blood pressure and intracellular sodium in hypertensive blacks.
1990 Apr
Systemic and regional hemodynamic interactions of perindopril and nitrendipine in the spontaneously hypertensive rat.
1990 Apr
Lacidipine: a calcium antagonist with potent and long-lasting antihypertensive effects in animal studies.
1990 Apr
Preclinical pharmacology of Ro 31-6930, a new potassium channel opener.
1990 Feb
Nitrendipine decreases benzodiazepine withdrawal seizures but not the development of benzodiazepine tolerance or withdrawal signs.
1990 Nov
Regression of cardiovascular structural changes after long-term antihypertensive treatment with the calcium antagonist nitrendipine.
1991
Tolerance to nitrendipine in patients with arterial hypertension accompanying chronic renal failure.
1991
Microvascular effects of cocaine; interaction with nitrendipine and enalaprilat.
1991
The place of isradipine in the treatment of hypertension.
1991 Feb
Pharmacokinetics, bioavailability, metabolism and acute and chronic antihypertensive effects of nitrendipine in patients with chronic renal failure and moderate to severe hypertension.
1991 Mar
Acute and short-term effects of nitrendipine and diltiazem at rest and during exercise in hypertensive patients.
1991 Nov-Dec
Adverse effect of the calcium channel blocker nitrendipine on nephrosclerosis in rats with renovascular hypertension.
1992 Aug
Effects of nitrendipine, chlordiazepoxide, flumazenil and baclofen on the increased anxiety resulting from alcohol withdrawal.
1992 Jan
Nocturnal hypotension and ACE inhibitors.
1993 Jun
Treatment of hypertensive emergency. Comparison of a new dosage form of the calcium antagonist nitrendipine with nifedipine capsules.
1994
Combination treatment of enalapril with nitrendipine in rats with renovascular hypertension.
1994 Jan
Delayed development of hypertension after short-term nitrendipine treatment.
1994 Jul
Doxazosin versus nitrendipine: a double-blind comparative study in patients adhering to a sodium-restricted diet.
1994 Jun
Effect of indomethacin on blood pressure control during treatment with nitrendipine.
1995 Sep
Influence of the angiotensin II type 1 receptor gene polymorphism on the effects of perindopril and nitrendipine on arterial stiffness in hypertensive individuals.
1996 Dec
Antihypertensive effects of trandolapril and nitrendipine in the elderly: a controlled trial with special emphasis on time effect profiles.
1996 Jan
Nitrendipine and enalapril improve albuminuria and glomerular filtration rate in non-insulin dependent diabetes.
1996 Jun
L-type calcium channels regulate gastrin release from human antral G cells.
1997 Aug
Evaluation of the efficacy and tolerability of nitrendipine in reducing both pressure and left ventricular mass in hypertensive type 2 diabetic patients.
1997 Aug
Characterization of the cloned human intermediate-conductance Ca2+-activated K+ channel.
1998 Sep
Synergism of hydrochlorothiazide and nitrendipine on reduction of blood pressure and blood pressure variability in spontaneously hypertensive rats.
2006 Dec
Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms.
2009 Feb
Differential roles of dihydropyridine calcium antagonist nifedipine, nitrendipine and amlodipine on gentamicin-induced renal tubular toxicity in rats.
2009 Oct 12
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
Prevention of hypertensive crises in rats induced by acute and chronic norepinephrine excess.
2010 Oct
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Deoxynivalenol (Vomitoxin)-Induced Cholecystokinin and Glucagon-Like Peptide-1 Release in the STC-1 Enteroendocrine Cell Model Is Mediated by Calcium-Sensing Receptor and Transient Receptor Potential Ankyrin-1 Channel.
2015 Jun
Patents

Patents

DE2117571
1
JP2007512338A
11
JP2007512339A
43
JP2007525670A
148
JP2011510003A
48
JP4744875B2
29
JPS6133128A
1
US3799934
1
US3799936
1
US4724141
1

Sample Use Guides

In Vivo Use Guide
Start with 5-20 mg once daily. May be increased to 40 mg in 1 or 2 doses. In hepatic disease reduce the dose to 5 to 10 mg daily.
Route of Administration: Oral
In Vitro Use Guide
At 1 and 10 uM, nitrendipine reduced peak Cav1.2a1 currents by 64+/-3% (n=4) and 81+/-1% (n=4), respectively, but at these same concentrations only inhibited Cav1.3a1 currents by 23+/-1% (n=8) and 53+/-2% (n=8), respectively.
Name Type Language
NITRENDIPINE
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, ETHYL METHYL ESTER
Common Name English
NITRENDIPINE [USAN]
Common Name English
NITRENDIPINE [EP MONOGRAPH]
Common Name English
BAYPRESS
Brand Name English
BAY-E-5009
Code English
(±)-BAY-E-5009
Code English
NSC-758466
Code English
NITRENDIPINE [MI]
Common Name English
NITRENDIPINE [MART.]
Common Name English
(±)-ETHYL METHYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(M-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLATE
Systematic Name English
NIDREL
Common Name English
NITRENDIPINE [JAN]
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-ETHYL 5-METHYL ESTER
Common Name English
NITREPIN
Common Name English
(±)-NITRENDIPINE
Common Name English
Nitrendipine [WHO-DD]
Common Name English
DEITEN
Common Name English
NITRENDIPINE [EP IMPURITY]
Common Name English
BAYOTENSIN
Brand Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, ETHYL METHYL ESTER, (±)-
Common Name English
nitrendipine [INN]
Common Name English
BAY E 5009
Code English
Classification Tree Code System Code
WHO-VATC QC09BB06
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
WHO-ATC C08CA08
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
NCI_THESAURUS C333
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
WHO-ATC C09BB06
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
WHO-VATC QC08CA08
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
Code System Code Type Description
LACTMED
Nitrendipine
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
DRUG BANK
DB01054
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL475534
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
CHEBI
7582
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
PUBCHEM
4507
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
INN
4739
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
254-513-1
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
NSC
758466
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID0023373
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
FDA UNII
9B627AW319
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
DRUG CENTRAL
1947
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
MESH
D009568
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
RXCUI
7441
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY RxNorm
CAS
39562-70-4
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
IUPHAR
2334
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
EVMPD
SUB09320MIG
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
WIKIPEDIA
NITRENDIPINE
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
NCI_THESAURUS
C90821
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
MERCK INDEX
m7932
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY Merck Index
SMS_ID
100000090223
Created by admin on Sat Dec 16 16:54:56 GMT 2023 , Edited by admin on Sat Dec 16 16:54:56 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of NITRENDIPINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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