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Details

Stereochemistry RACEMIC
Molecular Formula C18H20N2O6
Molecular Weight 360.3619
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(C1c2cccc(c2)N(=O)=O)C(=O)OC)C

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 360.3619
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
81255
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7687
 0.9 µM [Kd]
Blocker
 0.97 nM [IC50]
Blocker
 1.08 nM [IC50]
Blocker
 3.59 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
7968
Nitrendipine

Approved Use

Nitrendipine is used to treat mild to moderate hypertension.
PubMed

PubMed

TitleDatePubMed
Mode of antihypertensive action of nitrendipine.
1984
Clinical and systemic hemodynamic effects of nitrendipine.
1984 Jun
The protective effect of nitrendipine on gentamicin acute renal failure in rats.
1985 Aug
Cosecretion of calcitonin and calcitonin gene-related peptide from cultured rat medullary thyroid C cells.
1989 Feb
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
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
Tolerance to nitrendipine in patients with arterial hypertension accompanying chronic renal failure.
1991
Microvascular effects of cocaine; interaction with nitrendipine and enalaprilat.
1991
Acute and short-term effects of nitrendipine and diltiazem at rest and during exercise in hypertensive patients.
1991 Nov-Dec
Doxazosin versus nitrendipine: a double-blind comparative study in patients adhering to a sodium-restricted diet.
1994 Jun
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
Characterization of the cloned human intermediate-conductance Ca2+-activated K+ channel.
1998 Sep
Neuronal Ca(V)1.3alpha(1) L-type channels activate at relatively hyperpolarized membrane potentials and are incompletely inhibited by dihydropyridines.
2001 Aug 15
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Patents

Patents

DE2117571
1
JP2007512338A
10
JP2007512339A
39
JP2007525670A
149
JP2011510003A
44
JP4744875B2
28
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 Fri Jun 25 21:16:54 UTC 2021
Edited
by admin
on Fri Jun 25 21:16:54 UTC 2021
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
DEITEN
Common Name English
NITRENDIPINE [EP]
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
NITRENDIPINE [WHO-DD]
Common Name English
BAY E 5009
Code English
Classification Tree Code System Code
WHO-VATC QC09BB06
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
WHO-ATC C08CA08
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
NCI_THESAURUS C333
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
WHO-ATC C09BB06
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
WHO-VATC QC08CA08
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
Code System Code Type Description
LACTMED
Nitrendipine
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
DRUG BANK
DB01054
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
ChEMBL
CHEMBL475534
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
PUBCHEM
4507
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
INN
4739
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
ECHA (EC/EINECS)
254-513-1
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
EPA CompTox
39562-70-4
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
FDA UNII
9B627AW319
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
DRUG CENTRAL
1947
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
MESH
D009568
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
RXCUI
7441
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY RxNorm
CAS
39562-70-4
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
IUPHAR
2334
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
EVMPD
SUB09320MIG
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
WIKIPEDIA
NITRENDIPINE
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
NCI_THESAURUS
C90821
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY
MERCK INDEX
M7932
Created by admin on Fri Jun 25 21:16:54 UTC 2021 , Edited by admin on Fri Jun 25 21:16:54 UTC 2021
PRIMARY Merck Index
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
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