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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
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
Mode of antihypertensive action of nitrendipine.
1984
Renal effects of 1,4-dihydropyridines in animal models of hypertension and renal failure.
1987
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
Cocaine-induced small vessel spasm in isolated rat hearts.
1989 Jul
[The effect of calcium antagonist nitrendipine on the morphological picture of experimentally-produced myocardial injuries in rats].
1990
Adverse effect of the calcium channel blocker nitrendipine on nephrosclerosis in rats with renovascular hypertension.
1992 Aug
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
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
Nitrendipine and enalapril improve albuminuria and glomerular filtration rate in non-insulin dependent diabetes.
1996 Jun
Evaluation of the efficacy and tolerability of nitrendipine in reducing both pressure and left ventricular mass in hypertensive type 2 diabetic patients.
1997 Aug
Haloperidol-induced catalepsy is influenced by calcium channel antagonists.
2000 May-Jun
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
Synergism of hydrochlorothiazide and nitrendipine on reduction of blood pressure and blood pressure variability in spontaneously hypertensive rats.
2006 Dec
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
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:54:55 GMT 2023
Edited
by admin
on Sat Dec 16 16:54:55 GMT 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 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
Related Record Type Details
VOLTAGE-DEPENDENT L-TYPE CALCIUM CHANNEL SUBUNIT ALPHA-1D
TARGET -> INHIBITOR
Structure of NITRENDIPINE, (R)-
ENANTIOMER -> RACEMATE
Structure of Nitrendipine H-3
LABELED -> NON-LABELED
Structure of NITRENDIPINE, (S)-
ENANTIOMER -> RACEMATE
Voltage-dependent L-type calcium channel subunit alpha-1C (Rat)
TARGET -> INHIBITOR
BINDING
IC50
Related Record Type Details
Structure of NITRENDIPINE
ACTIVE MOIETY
NIH
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