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
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
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 | ( + / - ) |
DescriptionSources: http://www.hmdb.ca/metabolites/HMDB15187Curator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009568
Sources: http://www.hmdb.ca/metabolites/HMDB15187
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10884437 |
0.9 µM [Kd] | ||
Target ID: CHEMBL2529 Sources: https://www.drugbank.ca/drugs/DB01054 |
0.97 nM [IC50] | ||
Target ID: CHEMBL2830 Sources: https://www.drugbank.ca/drugs/DB01054 |
1.08 nM [IC50] | ||
Target ID: CHEMBL4138 Sources: https://www.drugbank.ca/drugs/DB01054 |
3.59 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Nitrendipine Approved UseNitrendipine is used to treat mild to moderate hypertension. |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11487617
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
Edited
Fri Jun 25 21:16:54 UTC 2021
by
admin
on
Fri Jun 25 21:16:54 UTC 2021
|
Record UNII |
9B627AW319
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR | |||
|
ENANTIOMER -> RACEMATE | |||
|
ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |