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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
Molecular Formula C18H20N2O6
Molecular Weight 360.3612
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 0.9 µM [Kd]
Blocker
534
 0.97 nM [IC50]
Blocker
534
 1.08 nM [IC50]
Blocker
534
 3.59 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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
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
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
Treatment of hypertension in the elderly with a new calcium channel blocking drug, nitrendipine.
1989 Jan
[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
Microvascular effects of cocaine; interaction with nitrendipine and enalaprilat.
1991
The place of isradipine in the treatment of hypertension.
1991 Feb
Arterial and antihypertensive effects of nitrendipine: a double-blind comparison versus placebo.
1992 Dec
Effect of antihypertensive treatment with nitrendipine on left ventricular mass and diastolic filling in patients with mild to moderate hypertension.
1992 Jan
Nocturnal hypotension and ACE inhibitors.
1993 Jun
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
Effects of the calcium antagonists verapamil and nitrendipine on carbamazepine withdrawal.
1999 Dec
Nitrendipine-induced subacute cutaneous lupus erythematosus.
2003 Mar-Apr
Enhanced interleukin-4 production in CD4+ T cells and elevated immunoglobulin E levels in antigen-primed mice by bisphenol A and nonylphenol, endocrine disruptors: involvement of nuclear factor-AT and Ca2+.
2003 May
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms.
2009 Feb
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
42
JP2007525670A
147
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:21:10 UTC 2023
Edited
by admin
on Thu Jul 06 22:21:10 UTC 2023
Record UNII
9B627AW319
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
WHO-ATC C08CA08
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
NCI_THESAURUS C333
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
WHO-ATC C09BB06
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
WHO-VATC QC08CA08
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
Code System Code Type Description
LACTMED
Nitrendipine
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
DRUG BANK
DB01054
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL475534
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
CHEBI
7582
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
PUBCHEM
4507
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
INN
4739
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
254-513-1
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
NSC
758466
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID0023373
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
FDA UNII
9B627AW319
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
DRUG CENTRAL
1947
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
MESH
D009568
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
RXCUI
7441
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY RxNorm
CAS
39562-70-4
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
IUPHAR
2334
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
EVMPD
SUB09320MIG
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
WIKIPEDIA
NITRENDIPINE
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
NCI_THESAURUS
C90821
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
MERCK INDEX
M7932
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY Merck Index
SMS_ID
100000090223
Created by admin on Thu Jul 06 22:21:11 UTC 2023 , Edited by admin on Thu Jul 06 22:21:11 UTC 2023
PRIMARY
Related Record Type Details
VOLTAGE-DEPENDENT L-TYPE CALCIUM CHANNEL SUBUNIT ALPHA-1D
TARGET -> INHIBITOR
Structure of NITRENDIPINE, (R)-
ENANTIOMER -> RACEMATE
Structure of NITRENDIPINE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of NITRENDIPINE
ACTIVE MOIETY
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