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
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
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 | ( + / - ) |
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 |
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Renal effects of 1,4-dihydropyridines in animal models of hypertension and renal failure. | 1987 |
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Calcium currents in embryonic and neonatal mammalian skeletal muscle. | 1988 Jun |
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Cocaine-induced small vessel spasm in isolated rat hearts. | 1989 Jul |
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[The effect of calcium antagonist nitrendipine on the morphological picture of experimentally-produced myocardial injuries in rats]. | 1990 |
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Systemic and regional hemodynamic interactions of perindopril and nitrendipine in the spontaneously hypertensive rat. | 1990 Apr |
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Lacidipine: a calcium antagonist with potent and long-lasting antihypertensive effects in animal studies. | 1990 Apr |
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Microvascular effects of cocaine; interaction with nitrendipine and enalaprilat. | 1991 |
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The place of isradipine in the treatment of hypertension. | 1991 Feb |
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Pharmacokinetics, bioavailability, metabolism and acute and chronic antihypertensive effects of nitrendipine in patients with chronic renal failure and moderate to severe hypertension. | 1991 Mar |
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Arterial and antihypertensive effects of nitrendipine: a double-blind comparison versus placebo. | 1992 Dec |
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Effect of antihypertensive treatment with nitrendipine on left ventricular mass and diastolic filling in patients with mild to moderate hypertension. | 1992 Jan |
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Nocturnal hypotension and ACE inhibitors. | 1993 Jun |
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Combination treatment of enalapril with nitrendipine in rats with renovascular hypertension. | 1994 Jan |
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Doxazosin versus nitrendipine: a double-blind comparative study in patients adhering to a sodium-restricted diet. | 1994 Jun |
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Effect of indomethacin on blood pressure control during treatment with nitrendipine. | 1995 Sep |
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Characterization of the cloned human intermediate-conductance Ca2+-activated K+ channel. | 1998 Sep |
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Effects of the calcium antagonists verapamil and nitrendipine on carbamazepine withdrawal. | 1999 Dec |
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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 |
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[Effects of nitrendipine on circadian variation of blood pressure in inpatients with renal parenchymal hypertension: assessment by ambulatory blood pressure monitoring]. | 2004 Jul |
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Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance. | 2004 Nov |
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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 |
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
Sat Dec 16 16:54:55 UTC 2023
by
admin
on
Sat Dec 16 16:54:55 UTC 2023
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Record UNII |
9B627AW319
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QC09BB06
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WHO-ATC |
C08CA08
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NCI_THESAURUS |
C333
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WHO-ATC |
C09BB06
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WHO-VATC |
QC08CA08
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Code System | Code | Type | Description | ||
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Nitrendipine
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DB01054
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CHEMBL475534
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7582
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4507
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4739
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254-513-1
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758466
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DTXSID0023373
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9B627AW319
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1947
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D009568
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7441
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39562-70-4
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2334
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SUB09320MIG
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NITRENDIPINE
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C90821
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m7932
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100000090223
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
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ENANTIOMER -> RACEMATE |
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LABELED -> NON-LABELED |
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ENANTIOMER -> RACEMATE |
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TARGET -> INHIBITOR |
BINDING
IC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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