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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:46 UTC
Secondary Accession Numbers
  • HMDB15004
Metabolite Identification
Common NameAlprenolol
DescriptionAlprenolol is only found in individuals that have used or taken this drug. It is one of the adrenergic beta-antagonists used as an antihypertensive, anti-anginal, and anti-arrhythmic agent. [PubChem]Alprenolol non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. Also, with a more minor effect, by binding beta-2 receptors in the juxtaglomerular apparatus, alprenolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.
Alprenolol hydrochlorideHMDB
Astra brand OF alprenolol hydrochlorideHMDB
Made brand OF alprenolol hydrochlorideHMDB
Astra brand OF alprenolol benzoateHMDB
Aptin durilesHMDB
Chemical FormulaC15H23NO2
Average Molecular Weight249.3486
Monoisotopic Molecular Weight249.172878985
IUPAC Name1-[2-(prop-2-en-1-yl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
Traditional Name1-(isopropylamino)-3-[2-(prop-2-en-1-yl)phenoxy]propan-2-ol
CAS Registry Number13655-52-2
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting Point107 - 109 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.19 g/LNot Available
LogP2.8Not Available
Predicted Properties
Water Solubility0.19 g/LALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity74.66 m³·mol⁻¹ChemAxon
Polarizability29.38 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-8920000000-21e1f9aacdf6f681239aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000x-3911000000-c0508ebc2143aa8f5821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2390000000-b40bd20c564639646d59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xu-9840000000-b699adf3065f5f8a80a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-38c31766bb53b5388936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-1790000000-9b9b80a1076fdfb513b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-5b3c063605beb0203b32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-5900000000-1e30f9cbcedc79974a16Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00866 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00866 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00866
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2035
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlprenolol
METLIN IDNot Available
PubChem Compound2119
PDB IDNot Available
ChEBI ID51211
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available


General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
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  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
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  1. Surman AJ, Doggrell SA: Alprenolol and bromoacetylalprenololmenthane are competitive slowly reversible antagonists at the beta 1-adrenoceptors of rat left atria. J Cardiovasc Pharmacol. 1993 Jan;21(1):35-9. [PubMed:7678677 ]
  2. De Ponti F, Cosentino M, Costa A, Girani M, Gibelli G, D'Angelo L, Frigo G, Crema A: Inhibitory effects of SR 58611A on canine colonic motility: evidence for a role of beta 3-adrenoceptors. Br J Pharmacol. 1995 Apr;114(7):1447-53. [PubMed:7606348 ]
  3. 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 ]
  4. Brahmadevara N, Shaw AM, MacDonald A: Evidence against beta 3-adrenoceptors or low affinity state of beta 1-adrenoceptors mediating relaxation in rat isolated aorta. Br J Pharmacol. 2003 Jan;138(1):99-106. [PubMed:12522078 ]
  5. Im MJ, Holzhofer A, Bottinger H, Pfeuffer T, Helmreich EJ: Interactions of pure beta gamma-subunits of G-proteins with purified beta 1-adrenoceptor. FEBS Lett. 1988 Jan 25;227(2):225-9. [PubMed:2828119 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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:
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Molecular weight:
  1. Brodde OE, Wang XL, O'Hara N, Daul A, Schiess W: Effect of propranolol, alprenolol, pindolol, and bopindolol on beta 2-adrenoceptor density in human lymphocytes. J Cardiovasc Pharmacol. 1986;8 Suppl 6:S70-3. [PubMed:2439825 ]
  2. Brodde OE, Daul A, Stuka N, O'Hara N, Borchard U: Effects of beta-adrenoceptor antagonist administration on beta 2-adrenoceptor density in human lymphocytes. The role of the "intrinsic sympathomimetic activity". Naunyn Schmiedebergs Arch Pharmacol. 1985 Feb;328(4):417-22. [PubMed:2859531 ]
  3. Abrahamsson T: The beta 1- and beta 2-adrenoceptor stimulatory effects of alprenolol, oxprenolol and pindolol: a study in the isolated right atrium and uterus of the rat. Br J Pharmacol. 1986 Apr;87(4):657-64. [PubMed:2871880 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
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  1. Millan MJ, Rivet JM, Canton H, Lejeune F, Bervoets K, Brocco M, Gobert A, Lefebvre de Ladonchamps B, Le Marouille-Girardon S, Verriele L, et al.: S 14671: a naphtylpiperazine 5-hydroxytryptamine1A agonist of exceptional potency and high efficacy possessing antagonist activity at 5-hydroxytryptamine1C/2 receptors. J Pharmacol Exp Ther. 1992 Aug;262(2):451-63. [PubMed:1323650 ]
  2. Darmani NA: Role of the inhibitory adrenergic alpha 2 and serotonergic 5-HT1A components of cocaine's actions on the DOI-induced head-twitch response in 5-HT2-receptor supersensitive mice. Pharmacol Biochem Behav. 1993 Jun;45(2):269-74. [PubMed:8392199 ]
  3. Kuipers W, Link R, Standaar PJ, Stoit AR, Van Wijngaarden I, Leurs R, Ijzerman AP: Study of the interaction between aryloxypropanolamines and Asn386 in helix VII of the human 5-hydroxytryptamine1A receptor. Mol Pharmacol. 1997 May;51(5):889-96. [PubMed:9145928 ]
  4. Misane I, Johansson C, Ogren SO: Analysis of the 5-HT1A receptor involvement in passive avoidance in the rat. Br J Pharmacol. 1998 Oct;125(3):499-509. [PubMed:9806333 ]