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Alprenolol

July 24, 2017
Common Name

Alprenolol Description

Alprenolol 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 resliting in a decrease in heart rate and blood pressure. Also, with a more minor effect, by binding beta-2 receptors in the juxtaglomerliar 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1-(2-Allylphenoxy)-3-isopropylamino-2-propanolChEBI 1-(O-Allylphenoxy)-3-(isopropylamino)-2-propanolChEBI AlfeprolChEBI AlprenololumChEBI AlpheprolHMDB Alprenolol hydrochlorideMeSH AptinDurilesMeSH AptinaMeSH Astra brand OF alprenolol hydrochlorideMeSH AptinMeSH AptineMeSH Made brand OF alprenolol hydrochlorideMeSH Astra brand OF alprenolol benzoateMeSH Aptin durilesMeSH Aptin-durilesMeSH

Chemical Formlia

C15H23NO2 Average Molecliar Weight

249.3486 Monoisotopic Molecliar Weight

249.172878985 IUPAC Name

1-[2-(prop-2-en-1-yl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol Traditional Name

1-(isopropylamino)-3-[2-(prop-2-en-1-yl)phenoxy]propan-2-ol CAS Registry Number

13655-52-2 SMILES

CC(C)NCC(O)COC1=CC=CC=C1CC=C

InChI Identifier

InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3

InChI Key

PAZJSJFMUHDSTF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Kingdom

Organic compounds Super Class

Benzenoids Class

Phenol ethers Sub Class

Not Available Direct Parent

Phenol ethers Alternative Parents

  • Phenoxy compounds
  • Alkyl aryl ethers
  • Secondary alcohols
  • 1,2-aminoalcohols
  • Dialkylamines
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • 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

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • secondary alcohol (CHEBI:51211 )
  • secondary amino compound (CHEBI:51211 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic beta-Antagonists
  • Anti-Arrhythmia Agents
  • Antiarrhythmic Agents
  • Antihypertensive Agents
  • Sympatholytics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point107 – 109 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.88e-01 g/LNot Available LogP2.8Not Available

    Predicted Properties

    Property Value Source Water Solubility0.19 mg/mLALOGPS logP2.59ALOGPS logP2.69ChemAxon logS-3.1ALOGPS pKa (Strongest Acidic)14.09ChemAxon pKa (Strongest Basic)9.67ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area41.49 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity74.66 m3·mol-1ChemAxon Polarizability29.38 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Alprenolol PathwaySMP00297Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00866

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00866

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00866 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2035 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15004 Metagene Link

    HMDB15004 METLIN ID

    Not Available PubChem Compound

    2119 PDB ID

    Not Available ChEBI ID

    51211

    Product: Valifenalate

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    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:
    CYP2D6
    Uniprot ID:
    P10635
    Molecular weight:
    55768.94
    References
    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
    Gene Name:
    ADRB1
    Uniprot ID:
    P08588
    Molecular weight:
    51322.1
    References
    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, DAngelo 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:
    ADRB2
    Uniprot ID:
    P07550
    Molecular weight:
    46458.3
    References
    1. Brodde OE, Wang XL, OHara 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, OHara 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
    Gene Name:
    HTR1A
    Uniprot ID:
    P08908
    Molecular weight:
    46106.3
    References
    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 cocaines 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 ]

    PMID: 24659806

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