Nadolol

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Nadolol
Nadolol.svg
Systematic (IUPAC) name
* rel-(2R,3S)-5-{[(2R)-3-(tert-butylamino)-2-hydroxypropyl]oxy}-1,2,3,4-tetrahydronaphthalene-2,3-diol
  • (2R*,3S*)-5-{[(2R*)-3-(tert-butylamino)-2-hydroxypropyl]oxy}-1,2,3,4-tetrahydronaphthalene-2,3-diol
Clinical data
Trade names Corgard
AHFS/Drugs.com monograph
MedlinePlus a682666
Pregnancy
category
  • US: C (Risk not ruled out)
Legal status
Routes of
administration		 Oral
Pharmacokinetic data
Protein binding 30%
Metabolism Nil
Biological half-life 14-24 hours
Excretion Renal and fecal (unchanged)
Identifiers
CAS Number 42200-33-9 YesY
ATC code C07AA12 (WHO)
PubChem CID: 39147
IUPHAR/BPS 554
DrugBank DB01203 YesY
ChemSpider 35815 YesY
UNII FEN504330V YesY
KEGG D00432 YesY
ChEMBL CHEMBL649 YesY
Chemical data
Formula C17H27NO4
Molecular mass 309.401 g/mol
  • OC(CNC(C)(C)C)COc1cccc2c1C[C@H](O)[C@H](O)C2
  • 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 YesY
  • Key:VWPOSFSPZNDTMJ-UCWKZMIHSA-N YesY
  (verify)

Nadolol (Corgard) is a non-selective beta blocker used in the treatment of high blood pressure and chest pain. Additionally, it is often prescribed in the treatment of atrial fibrillation, migraine headaches, and complications of cirrhosis.

Medical uses

Nadolol is used to treat hypertension and for long-term treatment of angina pectoris and is approved by the FDA for these purposes.[1]

It is regularly used off-label[1] for control of heart rate in people with atrial fibrillation,[2] prevention of migraine headaches;[3] prevention of bleeding veins in people with portal hypertension caused by cirrhosis;[4] and to treat people with high levels of thyroid hormone.[5]

Nadolol is one of the preferred beta-blockers in the management of patients with LQTS for shortening of the QT interval and prevention of ventricular arrhythmia. It is more efficacious than metoprolol in the prevention of breakthrough cardiac events while on therapy and is equivalent to propranolol.[6] Nadolol has the advantage of once daily dosing and thus improved patient compliance. For patients with decreased renal function, nadolol may be dosed less often.[7] It has also been found to be useful (off-label) for several neurological disorders such as the prevention of migraine attacks,[8] attention deficit/hyperactivity disorder(ADHD)[9][10][11] and its use has been explored as a treatment for essential tremor[12] and Parkinson's disease[13] but neither is well established.[14][15][16]

Side effects

The most common side effects include dizziness and fatigue.[13]

Contraindications

Nadolol and other beta blockers should be used with cautions in people with heart failure and its use should not be abruptly stopped. It is contraindicated for people with asthma, a slow heart rate and certain severe heart problems.[17]

Mechanism of action

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Main article: Beta-blocker

Nadolol is a non-selective beta blocker; that is, it non-selectively blocks both beta-1 and beta-2 receptors. It has a preference for beta-1 receptors, which are predominantly located in the heart, thereby inhibiting the effects of catecholamines and causing a decrease in heart rate and blood pressure. Its inhibition of beta-2 receptors, which are mainly located in the bronchial smooth muscle of the airways, leads to airway constriction similar to that seen in asthma. Inhibition of beta-1 receptors in the juxtaglomerular apparatus of the kidney inhibits the renin-angiotensin system, causing a decrease in vasoconstriction and a decrease in water retention. Nadolol's inhibition of beta-1 receptors in the heart and kidney leads to its effects on lowering blood pressure.

The drug impairs AV node conduction and decreases sinus rate.

Nadolol may also increase plasma triglycerides and decrease HDL-cholesterol levels.

Chemistry

Nadolol is a mixture of stereoisomers. It is polar and hydrophilic, with low lipid solubility.[18]

Four stereoisomers of nadolol

See also

References

  1. ↑ 1.0 1.1 Nadolol entry in AccessMedicine. McGraw-Hill Global Education Holdings, LLC. Accessed November 8, 2014
  2. ↑ January CT, et al 2014 AHA/ACC/HRS Guideline for the Management of Patients With Atrial Fibrillation: A Report of the American College of Cardiology/American Heart Association Task Force on Practice Guidelines and the Heart Rhythm Society. Circulation. 2014 Apr 10. PMID 24682347
  3. ↑ Silberstein SD et al. Evidence-based guideline update: pharmacologic treatment for episodic migraine prevention in adults: report of the Quality Standards Subcommittee of the American Academy of Neurology and the American Headache Society. Neurology. 2012 Apr 24;78(17):1337-45. PMID 22529202 PMC 3335452
  4. ↑ Giannelli V et al. Beta-blockers in liver cirrhosis. Ann Gastroenterol. 2014;27(1):20-26. PMID 24714633 PMC 3959530
  5. ↑ Bahn RS et al, “Hyperthyroidism and Other Causes of Thyrotoxicosis: Management Guidelines of the American Thyroid Association and American Association of Clinical Endocrinologists,” Thyroid, 2011, 21(6):593-646. PMID 21510801
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ http://reference.medscape.com/drug/corgard-nadolol-342361
  8. ↑ http://patient.info/medicine/nadolol-a-beta-blocker-corgard
  9. ↑ https://books.google.com/books?id=EkyTTvjNRZAC&pg=PA669&lpg=PA669&dq=Nadolol+for+ADHD&source=bl&ots=AHBVTAhCwv&sig=w0nW8Plyub3GN87J7itGz1fB11Y&hl=en&sa=X&ei=UAjRVMWkJoatyQSDzoDQCA&ved=0CFEQ6AEwBTgK#v=onepage&q=Nadolol%20for%20ADHD&f=false
  10. ↑ http://psychcentral.com/disorders/sx1t.htm
  11. ↑ http://www.doctorshangout.com/profiles/blogs/nadolol-nonselective-long-acting-beta-blocker
  12. ↑ Zesiewicz TA et al. Evidence-based guideline update: treatment of essential tremor: report of the Quality Standards subcommittee of the American Academy of Neurology. Neurology. 2011 Nov 8;77(19):1752-5. PMID 22013182 PMC 3208950
  13. ↑ 13.0 13.1 U.S. National Library of Medicine Nadolol entry in Medline Plus
  14. ↑ http://onlinelibrary.wiley.com/doi/10.1002/ana.410160412/abstract
  15. ↑ http://www.nlm.nih.gov/medlineplus/druginfo/meds/a682666.html
  16. ↑ http://www.drugs.com/dosage/nadolol.html
  17. ↑ Corgard Label
  18. ↑ Bragg W et al. Optimized separation of beta-blockers with multiple chiral centers using capillary electrochromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Nov 1;875(1):304-16. PMID 18619928 PMC 2680439
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