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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:25 UTC
HMDB IDHMDB0015334
Secondary Accession Numbers
  • HMDB15334
Metabolite Identification
Common NameNadolol
DescriptionNadolol is only found in individuals that have used or taken this drug. It is a non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for migraine disorders and for tremor. [PubChem]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.
Structure
Data?1582753285
Synonyms
ValueSource
CorgardKegg
SolgolHMDB
Chemical FormulaC17H27NO4
Average Molecular Weight309.4006
Monoisotopic Molecular Weight309.194008357
IUPAC Name(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol
Traditional Namenadolol
CAS Registry Number42200-33-9
SMILES
CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2
InChI Identifier
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
InChI KeyVWPOSFSPZNDTMJ-UCWKZMIHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • Alkyl aryl ether
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point124 - 136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.25 g/LNot Available
LogP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.25 g/LALOGPS
logP1.23ALOGPS
logP0.87ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)13.59ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area81.95 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.53 m³·mol⁻¹ChemAxon
Polarizability34.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lyo-4490000000-f1ce44aef531d74d12eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03k9-9153380000-2521536c2b1d3ead6115Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0k92-2920000000-2a6eb574de4bc8d52292Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0019000000-fdb4087c676d8d8d4a8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0092000000-e09452da687c6073a284Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uk9-4690000000-81baaf08e07647128956Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0kmi-4930000000-adbaba8c066f6c5c5558Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0aba-3900000000-3784678375e682bb5b2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05te-3900000000-52bc796915dc7eb2ff30Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ik9-0379000000-d94563052914b6b9e468Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0k92-2920000000-2a6eb574de4bc8d52292Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2497000000-cb7ab3bdec4fd928a6f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6491000000-e8d7e7ecf92155b5e141Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022i-9700000000-776ddc0e9892504d78f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1839000000-a1c8086c3bd17d51e494Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0900000000-42e8fea24e6bfc13bc9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-1900000000-ed7b5fe1e6fe690cabc7Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01203 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01203 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01203
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID35815
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNadolol
METLIN IDNot Available
PubChem Compound39147
PDB IDNot Available
ChEBI ID127570
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Wheeldon NM, McDevitt DG, Lipworth BJ: The effects of lower than conventional doses of oral nadolol on relative beta 1/beta 2-adrenoceptor blockade. Br J Clin Pharmacol. 1994 Aug;38(2):103-8. [PubMed:7981009 ]
  3. Koshiji M, Ito H, Minatoguchi S, Watanabe H, Imai Y, Kakami M, Hirakawa S: A comparison of guanfacine, bunazosin, atenolol and nadolol on blood pressure and plasma noradrenaline responses to cold pressor testing. Clin Exp Pharmacol Physiol. 1992 Jul;19(7):481-8. [PubMed:1354084 ]
  4. Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]
  5. Varma DR: Ligand-independent negative chronotropic responses of rat and mouse right atria to beta-adrenoceptor antagonists. Can J Physiol Pharmacol. 1999 Dec;77(12):943-9. [PubMed:10606440 ]
  6. Wheeldon NM, McDevitt DG, Lipworth BJ: Cardiac effects of the beta 3-adrenoceptor agonist BRL35135 in man. Br J Clin Pharmacol. 1994 Apr;37(4):363-9. [PubMed:7912539 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Wheeldon NM, McDevitt DG, Lipworth BJ: The effects of lower than conventional doses of oral nadolol on relative beta 1/beta 2-adrenoceptor blockade. Br J Clin Pharmacol. 1994 Aug;38(2):103-8. [PubMed:7981009 ]
  3. Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774 ]
  4. Liu YL, Toubro S, Astrup A, Stock MJ: Contribution of beta 3-adrenoceptor activation to ephedrine-induced thermogenesis in humans. Int J Obes Relat Metab Disord. 1995 Sep;19(9):678-85. [PubMed:8574280 ]
  5. Wheeldon NM, McDevitt DG, Lipworth BJ: Evaluation of in vivo partial beta 1/beta 2-agonist activity: a dose-ranging study with carteolol. Br J Clin Pharmacol. 1992 Apr;33(4):411-6. [PubMed:1349493 ]
  6. Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [PubMed:8953513 ]