Posted inUncategorized

Salmeterol

July 24, 2017
Common Name

Salmeterol Description

Salmeterol is only found in individuals that have used or taken this drug. It is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive plimonary disease COPD. Salmeterols long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the moleclie to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimliation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source SereventChEMBL GR-33343XChEMBL SalmaterolChEMBL GR-33343-XChEMBL Salmeterol xinafoateMeSH Xinafoate, salmeterolMeSH

Chemical Formlia

C25H37NO4 Average Molecliar Weight

415.5656 Monoisotopic Molecliar Weight

415.272258677 IUPAC Name

4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol Traditional Name

salmeterol CAS Registry Number

89365-50-4 SMILES

OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2

InChI Key

GIIZNNXWQWCKIB-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Benzyl alcohols Direct Parent

Benzyl alcohols Alternative Parents

  • Aralkylamines
  • 1-hydroxy-2-unsubstituted benzenoids
  • Secondary alcohols
  • 1,2-aminoalcohols
  • Dialkylamines
  • Dialkyl ethers
  • Primary alcohols
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Aromatic alcohols

    • Substituents

  • Benzyl alcohol
  • Phenol
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • secondary alcohol (CHEBI:64064 )
  • phenols (CHEBI:64064 )
  • secondary amino compound (CHEBI:64064 )
  • ether (CHEBI:64064 )
  • primary alcohol (CHEBI:64064 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic beta-Agonists
  • Bronchodilator Agents
  • Sympathomimetic

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point75.5 – 76.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.26e-03 g/LNot Available LogP4.2Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0023 mg/mLALOGPS logP3.82ALOGPS logP3.61ChemAxon logS-5.3ALOGPS pKa (Strongest Acidic)10.12ChemAxon pKa (Strongest Basic)9.4ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area81.95 Å2ChemAxon Rotatable Bond Count16ChemAxon Refractivity122.39 m3·mol-1ChemAxon Polarizability50.6 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-014i-0001900000-3c44a8f19551abbbb83aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001j-0029000000-43896c08fd5ce2a060e8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-4972000000-23117c7d5dc844d67897View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0006-6910000000-2afb08aff0a51fff0532View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0006-9800000000-5575125dd87cfbd258a8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-00kb-0229500000-3598d6091893d5b1aa38View in MoNA 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

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00938

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00938

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-2 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00938 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

    4968 KEGG Compound ID

    C07241 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Salmeterol NuGOwiki Link

    HMDB15073 Metagene Link

    HMDB15073 METLIN ID

    Not Available PubChem Compound

    5152 PDB ID

    Not Available ChEBI ID

    64064

    Product: Fabomotizole

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths. Ann Intern Med. 2006 Jun 20;144(12):904-12. Epub 2006 Jun 5. [PubMed:16754916 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    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 monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP3A5
    Uniprot ID:
    P20815
    Molecular weight:
    57108.065
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP3A7
    Uniprot ID:
    P24462
    Molecular weight:
    57525.03
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
    Gene Name:
    CYP2C8
    Uniprot ID:
    P10632
    Molecular weight:
    55824.275
    References
    1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
    2. 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. 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. Rong Y, Arbabian M, Thiriot DS, Seibold A, Clark RB, Ruoho AE: Probing the salmeterol binding site on the beta 2-adrenergic receptor using a novel photoaffinity ligand, [(125)I]iodoazidosalmeterol. Biochemistry. 1999 Aug 31;38(35):11278-86. [PubMed:10471277 ]
    2. Finney PA, Donnelly LE, Belvisi MG, Chuang TT, Birrell M, Harris A, Mak JC, Scorer C, Barnes PJ, Adcock IM, Giembycz MA: Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). Br J Pharmacol. 2001 Mar;132(6):1261-70. [PubMed:11250877 ]
    3. Green SA, Rathz DA, Schuster AJ, Liggett SB: The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s). Eur J Pharmacol. 2001 Jun 15;421(3):141-7. [PubMed:11516429 ]
    4. Meliton AY, Munoz NM, Liu J, Lambertino AT, Boetticher E, Myo S, Myou S, Zhu X, Johnson M, Leff AR: Blockade of LTC4 synthesis caused by additive inhibition of gIV-PLA2 phosphorylation: Effect of salmeterol and PDE4 inhibition in human eosinophils. J Allergy Clin Immunol. 2003 Aug;112(2):404-10. [PubMed:12897749 ]
    5. Brogden RN, Faulds D: Salmeterol xinafoate: a review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Allergol Immunopathol (Madr). 1992 Mar-Apr;20(2):72-84. [PubMed:1359777 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 15190076

    Last updated on