Metenolone acetate (CHEM043947)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:28:22 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043947
Identification
Common NameMetenolone acetate
ClassSmall Molecule
DescriptionMetenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.Side effects of metenolone acetate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage. Metenolone enanthate is a metenolone ester and a prodrug of metenolone in the body.Metenolone acetate was introduced for medical use in 1961. In addition to its medical use, metenolone acetate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit. It remains marketed for medical use only in a few countries, such as Japan and Moldova.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Metenolone acetateKegg
PrimobolanKegg
Metenolone acetic acidGenerator
Methenolone acetic acidGenerator
Methenolone acetate, (17beta)-isomerMeSH
Primobolan SMeSH
(1S,2S,7S,10R,11S,14S,15S)-2,3,15-Trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-14-yl acetic acidGenerator
Chemical FormulaC22H32O3
Average Molecular Mass344.495 g/mol
Monoisotopic Mass344.235 g/mol
CAS Registry Number434-05-9
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-2,3,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-14-yl acetate
Traditional Name(1S,2S,7S,10R,11S,14S,15S)-2,3,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-14-yl acetate
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)C=C(C)[C@]4(C)[C@@]3([H])CC[C@]12C)OC(C)=O
InChI IdentifierInChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1
InChI KeyPGAUJQOPTMSERF-QWQRBHLCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0025 g/LALOGPS
logP4.01ALOGPS
logP4.09ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.13 m³·mol⁻¹ChemAxon
Polarizability40.37 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0029000000-aa64d1ed7a122a4dbec7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9i-0396000000-cc0f9eb6110b3e5ea5bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-1971000000-5cdfe7d46ffdc03d84b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1009000000-ca8d024b7c0114563cedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-2019000000-17db6c517d4298e52594Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0l73-5092000000-9ba58ffcfbc321261ca0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetenolone acetate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID252372
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available