Posted inUncategorized

Methyltestosterone

July 24, 2017
Common Name

Methyltestosterone Description

A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedlie III drug in the US. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 17(alpha)-Methyl-Delta(4)-androsten-17(beta)-ol-3-oneChEBI 17-beta-Hydroxy-17-methylandrost-4-en-3-oneChEBI 17-MethyltestosteroneChEBI 17alpha-Methyl-3-oxo-4-androsten-17beta-olChEBI 17alpha-Methyl-Delta(4)-androsten-17beta-ol-3-oneChEBI 17alpha-MethyltestosteroneChEBI 17beta-Hydroxy-17-methylandrost-4-en-3-oneChEBI 4-Androstene-17alpha-methyl-17beta-ol-3-oneChEBI AndroidChEBI MethyltestosteronumChEBI MetiltestosteronaChEBI NSC-9701ChEBI TestredChEBI VirilonChEBI 17(a)-Methyl-delta(4)-androsten-17(b)-ol-3-oneGenerator 17(α)-methyl-δ(4)-androsten-17(β)-ol-3-oneGenerator 17-b-Hydroxy-17-methylandrost-4-en-3-oneGenerator 17-β-hydroxy-17-methylandrost-4-en-3-oneGenerator 17a-Methyl-3-oxo-4-androsten-17b-olGenerator 17α-methyl-3-oxo-4-androsten-17β-olGenerator 17a-Methyl-delta(4)-androsten-17b-ol-3-oneGenerator 17α-methyl-δ(4)-androsten-17β-ol-3-oneGenerator 17a-MethyltestosteroneGenerator 17α-methyltestosteroneGenerator 17b-Hydroxy-17-methylandrost-4-en-3-oneGenerator 17β-hydroxy-17-methylandrost-4-en-3-oneGenerator 4-Androstene-17a-methyl-17b-ol-3-oneGenerator 4-Androstene-17α-methyl-17β-ol-3-oneGenerator 17(a)-Methyl-δ(4)-androsten-17(b)-ol-3-oneGenerator 17a-Methyl-δ(4)-androsten-17b-ol-3-oneGenerator 17alpha-Methyl-delta-androsten-17beta-ol-3-oneHMDB 17 EpimethyltestosteroneMeSH 17 beta MethyltestosteroneMeSH 17alpha MethyltestosteroneMeSH MesteronMeSH 17 beta-MethyltestosteroneMeSH 17-EpimethyltestosteroneMeSH 17beta Hydroxy 17 methyl 4 androsten 3 oneMeSH 17beta MethyltestosteroneMeSH 17beta-Hydroxy-17-methyl-4-androsten-3-oneMeSH Android-25MeSH Global pharmaceutical brand OF methyltestosteroneMeSH ICN brand 1 OF methyltestosteroneMeSH ICN brand 2 OF methyltestosteroneMeSH 17 alpha MethyltestosteroneMeSH 17-alpha-MethyltestosteroneMeSH 17alpha-Methyl-testosteroneMeSH Android 25MeSH Android 5MeSH Android-5MeSH MetandrenMeSH Star brand OF methyltestosteroneMeSH 17 beta Hydroxy 17 methyl 4 androsten 3 oneMeSH 17 beta-Hydroxy-17-methyl-4-androsten-3-oneMeSH 17alpha Methyl testosteroneMeSH 17beta-MethyltestosteroneMeSH Android 10MeSH Android-10MeSH MesteroneMeSH MethitestMeSH OretonMeSH Schering brand OF methyltestosteroneMeSH TestovironMeSH

Chemical Formlia

C20H30O2 Average Molecliar Weight

302.451 Monoisotopic Molecliar Weight

302.224580204 IUPAC Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one Traditional Name

methyltestosterone CAS Registry Number

58-18-4 SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1

InChI Key

GCKMFJBGXUYNAG-HLXURNFRSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of mascliine characteristics. They also show profound effects on scalp and body hair in humans. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Steroids and steroid derivatives Direct Parent

Androgens and derivatives Alternative Parents

  • 3-oxo delta-4-steroids
  • 17-hydroxysteroids
  • Delta-4-steroids
  • Cyclohexenones
  • Tertiary alcohols
  • Cyclic alcohols and derivatives
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Androgen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • enone (CHEBI:27436 )
  • 3-oxo Delta(4)-steroid (CHEBI:27436 )
  • 17beta-hydroxy steroid (CHEBI:27436 )
  • C19 steroids (androgens) and derivatives (C07198 )
  • C19 steroids (androgens) and derivatives (LMST02020029 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anabolic Agents
  • Androgens
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormone Replacement Agents
  • 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 PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.39e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.014 mg/mLALOGPS logP3.61ALOGPS logP3.65ChemAxon logS-4.3ALOGPS pKa (Strongest Acidic)19.09ChemAxon pKa (Strongest Basic)-0.53ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area37.3 Å2ChemAxon Rotatable Bond Count0ChemAxon Refractivity89.07 m3·mol-1ChemAxon Polarizability35.65 Å3ChemAxon Number of Rings4ChemAxon 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 – , positivesplash10-0udi-1329000000-c8db8c2a5d8403c476e1View 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 MS

    Mass Spectrum (Electron Ionization)splash10-006x-7921000000-0e8f2747a2f3c8166048View in MoNA 1D NMR

    1H NMR SpectrumNot Available 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 DB06710

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06710

  • 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

    DB06710 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

    5788 KEGG Compound ID

    C07198 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Methyltestosterone NuGOwiki Link

    HMDB15655 Metagene Link

    HMDB15655 METLIN ID

    Not Available PubChem Compound

    6010 PDB ID

    Not Available ChEBI ID

    27436

    Product: Carbazochrome (sodium sulfonate)

    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 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. Acts as a 1,4-cineole 2-exo-monooxygenase.
    Gene Name:
    CYP2B6
    Uniprot ID:
    P20813
    Molecular weight:
    56277.81
    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:
    Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
    Gene Name:
    CYP19A1
    Uniprot ID:
    P11511
    Molecular weight:
    57882.48
    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 DNA binding
    Specific function:
    Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
    Gene Name:
    AR
    Uniprot ID:
    P10275
    Molecular weight:
    98987.9
    References
    1. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. [PubMed:17084172 ]
    2. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. [PubMed:17086931 ]
    3. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. doi: 10.14670/HH-22.107. [PubMed:17128417 ]
    4. Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. [PubMed:17202804 ]
    5. Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. [PubMed:17322500 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    Transporters

    General function:
    Involved in transporter activity
    Specific function:
    Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
    Gene Name:
    SLCO1A2
    Uniprot ID:
    P46721
    Molecular weight:
    74144.1
    References
    1. Lu R, Kanai N, Bao Y, Wolkoff AW, Schuster VL: Regulation of renal oatp mRNA expression by testosterone. Am J Physiol. 1996 Feb;270(2 Pt 2):F332-7. [PubMed:8779895 ]
    2. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894 ]
    3. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566 ]

    PMID: 22837009

    Last updated on