Posted inUncategorized

Mestranol

July 24, 2017
Common Name

Mestranol Description

Mestranol is only found in individuals that have used or taken this drug. It is the 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives. [PubChem]Mestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formliations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70%.Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globliin (SHBG), thyroid-binding globliin (TBG), and other serum proteins and suppress follicle-stimliating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratrieneChEBI (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratrieneChEBI 17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-olChEBI 3-Methoxy-17alpha-ethynylestradiolChEBI 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-olChEBI Ethynylestradiol 3-methyl etherChEBI MestranolumChEBI (+)-17a-Ethynyl-17b-hydroxy-3-methoxy-1,3,5(10)-estratrieneGenerator (+)-17α-ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratrieneGenerator (+)-17a-Ethynyl-17b-hydroxy-3-methoxy-1,3,5(10)-oestratrieneGenerator (+)-17α-ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-oestratrieneGenerator 17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17b-olGenerator 17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17β-olGenerator 3-Methoxy-17a-ethynylestradiolGenerator 3-Methoxy-17α-ethynylestradiolGenerator 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17b-olGenerator 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-olGenerator Ethinyl estradiol 3-methyl etherMeSH Ethinyl estradiol 3 methyl etherMeSH

Chemical Formlia

C21H26O2 Average Molecliar Weight

310.4299 Monoisotopic Molecliar Weight

310.193280076 IUPAC Name

(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol Traditional Name

mestranol CAS Registry Number

72-33-3 SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3

InChI Identifier

InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

InChI Key

IMSSROKUHAOUJS-MJCUULBUSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. Kingdom

Organic compounds Super Class

Lipids and lipid-like moleclies Class

Steroids and steroid derivatives Sub Class

Estrane steroids Direct Parent

Estrane steroids Alternative Parents

  • 17-hydroxysteroids
  • Phenanthrenes and derivatives
  • Tetralins
  • Anisoles
  • Alkyl aryl ethers
  • Ynones
  • Tertiary alcohols
  • Cyclic alcohols and derivatives
  • Acetylides
  • Hydrocarbon derivatives

    • Substituents

  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Ynone
  • Benzenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Acetylide
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homopolycyclic compound

    • Molecliar Framework

    Aromatic homopolycyclic compounds External Descriptors

  • terminal acetylenic compound (CHEBI:6784 )
  • aromatic ether (CHEBI:6784 )
  • 17beta-hydroxy steroid (CHEBI:6784 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Estrogens
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point150.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.77e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0038 mg/mLALOGPS logP3.89ALOGPS logP4.04ChemAxon logS-4.9ALOGPS pKa (Strongest Acidic)17.59ChemAxon pKa (Strongest Basic)-1.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area29.46 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity91.86 m3·mol-1ChemAxon Polarizability36.7 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key MS

    Mass Spectrum (Electron Ionization)splash10-01t9-1972000000-5e394201ba0e38e5391fView in MoNA 1D NMR

    13C NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • 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 DB01357

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01357

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 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

    DB01357 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

    6054 KEGG Compound ID

    C07618 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Mestranol NuGOwiki Link

    HMDB15446 Metagene Link

    HMDB15446 METLIN ID

    Not Available PubChem Compound

    6291 PDB ID

    Not Available ChEBI ID

    6784

    Product: Bedaquiline (fumarate)

    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:
    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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
    2. Schmider J, Greenblatt DJ, von Moltke LL, Karsov D, Vena R, Friedman HL, Shader RI: Biotransformation of mestranol to ethinyl estradiol in vitro: the role of cytochrome P-450 2C9 and metabolic inhibitors. J Clin Pharmacol. 1997 Mar;37(3):193-200. [PubMed:9089421 ]
    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
    Gene Name:
    ESR1
    Uniprot ID:
    P03372
    Molecular weight:
    66215.4
    References
    1. Dulos J, Vijn P, van Doorn C, Hofstra CL, Veening-Griffioen D, de Graaf J, Dijcks FA, Boots AM: Suppression of the inflammatory response in experimental arthritis is mediated via estrogen receptor alpha but not estrogen receptor beta. Arthritis Res Ther. 2010;12(3):R101. doi: 10.1186/ar3032. Epub 2010 May 24. [PubMed:20497523 ]
    2. Cleuren AC, Van der Linden IK, De Visser YP, Wagenaar GT, Reitsma PH, Van Vlijmen BJ: 17alpha-Ethinylestradiol rapidly alters transcript levels of murine coagulation genes via estrogen receptor alpha. J Thromb Haemost. 2010 Aug;8(8):1838-46. doi: 10.1111/j.1538-7836.2010.03930.x. Epub 2010 May 27. [PubMed:20524981 ]
    3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 12372020

    Last updated on