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 |
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Systemic and regional hemodynamics in normotensive and spontaneously hypertensive rats after slow-channel calcium blocker nitrendipine. | 1984 |
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Nitrendipine block of cardiac calcium channels: high-affinity binding to the inactivated state. | 1984 Oct |
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Antihypertensive treatment using calcium antagonists in combination with captopril rather than diuretics. | 1985 |
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Predictors of blood pressure increases after withdrawal of antihypertensive therapy. | 1985 Dec |
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Relative potency of a beta-blocking and a calcium entry blocking agent as antihypertensive drugs in black patients. | 1986 |
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Renal effects of 1,4-dihydropyridines in animal models of hypertension and renal failure. | 1987 |
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Nitrendipine-stimulated release of prostacyclin-like substance in normal and atherosclerotic animals. | 1987 Apr |
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Treatment of hypertension in the elderly with a new calcium channel blocking drug, nitrendipine. | 1989 Jan |
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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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Effects of nitrendipine and atenolol on blood pressure and intracellular sodium in hypertensive blacks. | 1990 Apr |
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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 |
|
Preclinical pharmacology of Ro 31-6930, a new potassium channel opener. | 1990 Feb |
|
Nitrendipine decreases benzodiazepine withdrawal seizures but not the development of benzodiazepine tolerance or withdrawal signs. | 1990 Nov |
|
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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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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Delayed development of hypertension after short-term nitrendipine treatment. | 1994 Jul |
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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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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 |
|
Antihypertensive effects of trandolapril and nitrendipine in the elderly: a controlled trial with special emphasis on time effect profiles. | 1996 Jan |
|
Nitrendipine and enalapril improve albuminuria and glomerular filtration rate in non-insulin dependent diabetes. | 1996 Jun |
|
L-type calcium channels regulate gastrin release from human antral G cells. | 1997 Aug |
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Evaluation of the efficacy and tolerability of nitrendipine in reducing both pressure and left ventricular mass in hypertensive type 2 diabetic patients. | 1997 Aug |
|
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 |
|
Nitrendipine-induced subacute cutaneous lupus erythematosus. | 2003 Mar-Apr |
|
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 |
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Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms. | 2009 Feb |
|
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 |
|
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 |
|
Deoxynivalenol (Vomitoxin)-Induced Cholecystokinin and Glucagon-Like Peptide-1 Release in the STC-1 Enteroendocrine Cell Model Is Mediated by Calcium-Sensing Receptor and Transient Receptor Potential Ankyrin-1 Channel. | 2015 Jun |
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
Thu Jul 06 22:21:10 UTC 2023
by
admin
on
Thu Jul 06 22:21:10 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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QC09BB06
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WHO-ATC |
C08CA08
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NCI_THESAURUS |
C333
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C09BB06
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WHO-VATC |
QC08CA08
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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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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |