Details
Stereochemistry | EPIMERIC |
Molecular Formula | C17H27NO4 |
Molecular Weight | 309.4006 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)NCC(O)COC1=C2C[C@H](O)[C@H](O)CC2=CC=C1
InChI
InChIKey=VWPOSFSPZNDTMJ-UCWKZMIHSA-N
InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12?,14-,15+/m1/s1
Molecular Formula | C17H27NO4 |
Molecular Weight | 309.4006 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB01203Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/018063s063lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01203
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/018063s063lbl.pdf
Nadolol is a nonselective beta-adrenergic receptor antagonist with a long half-life, and is structurally similar to propranolol. Clinical pharmacology studies have demonstrated beta-blocking activity by showing (1) reduction in heart rate and cardiac output at rest and on exercise, (2) reduction of systolic and diastolic blood pressure at rest and on exercise, (3) inhibition of isoproterenol-induced tachycardia, and (4) reduction of reflex orthostatic tachycardia. Nadolol has no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, nadolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action. Like other beta-adrenergic antagonists, nadolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Like propranolol and timolol, nadolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure. It also blocks beta-2 adrenergic receptors located in bronchiole smooth muscle, causing vasoconstriction. By binding beta-2 receptors in the juxtaglomerular apparatus, nadolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production. Nadolol therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively. Nadolol is used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL210 Sources: http://www.drugbank.ca/drugs/DB01203 |
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Target ID: CHEMBL213 Sources: http://www.drugbank.ca/drugs/DB01203 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | CORGARD Approved UseAngina Pectoris
CORGARD (nadolol) is indicated for the long-term management of patients with angina pectoris.
Hypertension
CORGARD (nadolol) is indicated for the treatment of hypertension, to lower blood pressure. Launch Date3.13545589E11 |
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Primary | CORGARD Approved UseAngina Pectoris
CORGARD (nadolol) is indicated for the long-term management of patients with angina pectoris.
Hypertension
CORGARD (nadolol) is indicated for the treatment of hypertension, to lower blood pressure. Launch Date3.13545589E11 |
PubMed
Title | Date | PubMed |
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[Verapamil-responsive ventricular tachycardia in small children: a case report and review of the literature]. | 1999 Feb |
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Chronic subcutaneous octreotide decreases gastrointestinal blood loss in blue rubber-bleb nevus syndrome. | 2001 Aug |
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Endoscopic ligation compared with combined treatment with nadolol and isosorbide mononitrate to prevent recurrent variceal bleeding. | 2001 Aug 30 |
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Beta-adrenoceptor blockade alters thymocyte differentiation in aged mice. | 2001 Feb |
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A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans. | 2001 Mar |
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Partition coefficients of beta-blockers in bile salt/lecithin micelles as a tool to assess the role of mixed micelles in gastrointestinal absorption. | 2001 Mar 15 |
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Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum. | 2001 Mar 23 |
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[Pharmacology of beta blockers and their significance for therapy of hypertension]. | 2002 Aug |
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Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium. | 2002 Jan |
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[Alteration in relaxation of atypical beta-adrenergic but not beta-3 receptors in arterial hypertension in the rat]. | 2002 Jul-Aug |
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Direct enantiomeric resolution of some cardiovascular agents using synthetic polymers imprinted with (-)-S-timolol as chiral stationary phase by thin layer chromatography. | 2002 Mar |
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Simultaneous determination of eight beta-blockers by gradient high-performance liquid chromatography with combined ultraviolet and fluorescence detection in corneal permeability studies in vitro. | 2002 May 25 |
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Beta-blockers no better than placebo in the treatment of vasovagal syncope. | 2002 Nov |
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Fenfluramine-induced immunosuppression: an in vivo analysis. | 2002 Nov 29 |
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LC determination of moclobemide and three metabolites in plasma. | 2002 Nov 7 |
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Modulation of L-type Ca2+ channels by beta3-adrenoceptor activation and the involvement of nitric oxide. | 2002 Sep-Oct |
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Acute down-regulation of antibody production following spinal cord injury: role of systemic catecholamines. | 2003 Aug |
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Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers. | 2003 Aug |
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beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor. | 2003 Aug 1 |
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Norepinephrine induces slow calcium signalling in murine brown preadipocytes through the beta-adrenoceptor/cAMP/protein kinase A pathway. | 2003 Feb |
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The modulatory effects of noradrenaline on vagal control of heart rate in the dogfish, Squalus acanthias. | 2003 May-Jun |
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Tail-suspension induced hyperthermia: a new measure of stress reactivity. | 2003 May-Jun |
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Evaluation of an immortalized retinal endothelial cell line as an in vitro model for drug transport studies across the blood-retinal barrier. | 2003 Sep |
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Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection. | 2004 Apr 20 |
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G-protein-coupled receptor chromatographic stationary phases. 2. Ligand-induced conformational mobility in an immobilized beta2-adrenergic receptor. | 2004 Dec 15 |
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The use of multi-frequency EPR techniques to identify the radicals produced in irradiated beta-blockers. | 2004 Jan |
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Management of cirrhosis and ascites. | 2004 Jul 15 |
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Increased infarct size in uremic rats: reduced ischemia tolerance? | 2004 Jun |
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Management of esophageal varices: an update from Digestive Disease Week and American Association for the Study of Liver Diseases 2003. | 2004 Jun |
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Catecholaminergic polymorphic ventricular tachycardia: successful emergency treatment with intravenous propranolol. | 2004 Mar |
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Chiral separation and modeling of the three-chiral-center beta-blocker drug nadolol by simulated moving bed chromatography. | 2004 May 7 |
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Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization. | 2004 Nov 26 |
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Beta-blocker goes on trial as asthma therapy. | 2004 Nov 4 |
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Exercise-provoked bidirectional ventricular tachycardia in a young woman. | 2004 Oct |
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Beta-blocker therapy failures in symptomatic probands with genotyped long-QT syndrome. | 2004 Sep-Oct |
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Norepinephrine in mice inhibits secretion of splenic IL-6 during the dark period but stimulates its secretion in the light period--possible role of the corticosterone tone. | 2005 Jan |
Sample Use Guides
The usual initial dose is 40 mg CORGARD (nadolol) once daily. Dosage may be gradually increased in 40 to 80 mg increments at 3 to 7 day intervals until optimum clinical response is obtained or there is pronounced slowing of the heart rate. The usual maintenance dose is 40 or 80 mg administered once daily. Doses up to 160 or 240 mg administered once daily may be needed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16382175
A 3-min pretreatment of H9C2 cells by 10 uM nadolol inhibited calcium increases, induced by exposure to cocaine
Substance Class |
Chemical
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Record UNII |
FEN504330V
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Record Status |
Validated (UNII)
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C07AA12
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C29576
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N0000175556
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C07BA12
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N0000000161
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1865
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1449700
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Nadolol
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42200-33-9
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758430
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CHEMBL649
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NADOLOL
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6532
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DB01203
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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