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Nandrolone decanoate

July 24, 2017
Common Name

Nandrolone decanoate Description

Nandrolone decanoate is only found in individuals that have used or taken this drug. It is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedlie III drug in the U.S. Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Deca-durabolinKegg Nandrolone decanoic acidGenerator Norandrostenolone decanoateHMDB Nortestosterone decanoateHMDB 19-Nor-4-androstene-17 beta-ol-3-one 17-decanoateMeSH DecadurobolinMeSH 17 beta-Hydroxyestr-4-en-3-one 17-decanoateMeSH RetabolilMeSH RetabolylMeSH 19-Nortestosterone decanoateMeSH DecadurabolinMeSH

Chemical Formlia

C28H44O3 Average Molecliar Weight

428.6472 Monoisotopic Molecliar Weight

428.329045274 IUPAC Name

(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl decanoate Traditional Name

nandrolone decanoate CAS Registry Number

360-70-3 SMILES

CCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C28H44O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h19,22-26H,3-18H2,1-2H3/t22-,23+,24+,25-,26-,28-/m0/s1

InChI Key

JKWKMORAXJQQSR-MOPIKTETSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Steroids and steroid derivatives Direct Parent

Steroid esters Alternative Parents

  • Estrogens and derivatives
  • 3-oxo delta-4-steroids
  • Delta-4-steroids
  • Cyclohexenones
  • Carboxylic acid esters
  • Monocarboxylic acids and derivatives
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Steroid ester
  • Estrogen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Estrane-skeleton
  • Delta-4-steroid
  • Cyclohexenone
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • steroid ester (CHEBI:7467 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anabolic Agents
  • Androgens
  • Cell signaling
  • 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 Point118 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP2.62HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.000157 mg/mLALOGPS logP5.96ALOGPS logP7.32ChemAxon logS-6.4ALOGPS pKa (Strongest Acidic)19.28ChemAxon pKa (Strongest Basic)-4.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area43.37 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity125.94 m3·mol-1ChemAxon Polarizability53.65 Å3ChemAxon Number of Rings4ChemAxon 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

  • 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 DB08804

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08804

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08804 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

    9296 KEGG Compound ID

    C08154 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Nandrolone_decanoate NuGOwiki Link

    HMDB15694 Metagene Link

    HMDB15694 METLIN ID

    Not Available PubChem Compound

    9677 PDB ID

    Not Available ChEBI ID

    774897

    Product: Dequalinium (Chloride)

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

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
    Gene Name:
    MAOB
    Uniprot ID:
    P27338
    Molecular weight:
    58762.475
    References
    1. Birgner C, Kindlundh-Hogberg AM, Oreland L, Alsio J, Lindblom J, Schioth HB, Bergstrom L: Reduced activity of monoamine oxidase in the rat brain following repeated nandrolone decanoate administration. Brain Res. 2008 Jul 11;1219:103-10. doi: 10.1016/j.brainres.2008.05.014. Epub 2008 May 17. [PubMed:18539264 ]
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
    Gene Name:
    MAOA
    Uniprot ID:
    P21397
    Molecular weight:
    59681.27
    References
    1. Birgner C, Kindlundh-Hogberg AM, Oreland L, Alsio J, Lindblom J, Schioth HB, Bergstrom L: Reduced activity of monoamine oxidase in the rat brain following repeated nandrolone decanoate administration. Brain Res. 2008 Jul 11;1219:103-10. doi: 10.1016/j.brainres.2008.05.014. Epub 2008 May 17. [PubMed:18539264 ]
    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. Takahashi K, Hallberg M, Magnusson K, Nyberg F, Watanabe Y, Langstrom B, Bergstrom M: Increase in [11C]vorozole binding to aromatase in the hypothalamus in rats treated with anabolic androgenic steroids. Neuroreport. 2007 Jan 22;18(2):171-4. [PubMed:17301684 ]
    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. Birgner C, Kindlundh-Hogberg AM, Alsio J, Lindblom J, Schioth HB, Bergstrom L: The anabolic androgenic steroid nandrolone decanoate affects mRNA expression of dopaminergic but not serotonergic receptors. Brain Res. 2008 Nov 13;1240:221-8. doi: 10.1016/j.brainres.2008.09.003. Epub 2008 Sep 13. [PubMed:18809391 ]

    PMID: 15084136

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