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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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
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
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
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
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
Combination treatment of enalapril with nitrendipine in rats with renovascular hypertension.
1994 Jan
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
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
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
[Effects of nitrendipine on circadian variation of blood pressure in inpatients with renal parenchymal hypertension: assessment by ambulatory blood pressure monitoring].
2004 Jul
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Differential roles of dihydropyridine calcium antagonist nifedipine, nitrendipine and amlodipine on gentamicin-induced renal tubular toxicity in rats.
2009 Oct 12
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
Patents

Sample Use Guides

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
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 UTC 2023
Edited
by admin
on Sat Dec 16 16:54:55 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 Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
WHO-ATC C08CA08
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
NCI_THESAURUS C333
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
WHO-ATC C09BB06
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
WHO-VATC QC08CA08
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
Code System Code Type Description
LACTMED
Nitrendipine
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
DRUG BANK
DB01054
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
ChEMBL
CHEMBL475534
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
CHEBI
7582
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
PUBCHEM
4507
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
INN
4739
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
ECHA (EC/EINECS)
254-513-1
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
NSC
758466
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID0023373
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
FDA UNII
9B627AW319
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
DRUG CENTRAL
1947
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
MESH
D009568
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
RXCUI
7441
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY RxNorm
CAS
39562-70-4
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
IUPHAR
2334
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
EVMPD
SUB09320MIG
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
WIKIPEDIA
NITRENDIPINE
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
NCI_THESAURUS
C90821
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
MERCK INDEX
m7932
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY Merck Index
SMS_ID
100000090223
Created by admin on Sat Dec 16 16:54:56 UTC 2023 , Edited by admin on Sat Dec 16 16:54:56 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
LABELED -> NON-LABELED
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
BINDING
IC50
Related Record Type Details
ACTIVE MOIETY