Fluoxymesterone (CHEM002367)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:34 UTC
Update Date2026-05-14 16:58:34 UTC
Accession NumberCHEM002367
Identification
Common NameFluoxymesterone
ClassSmall Molecule
DescriptionFluoxymesterone is only found in individuals that have used or taken this drug. It is an anabolic steroid that has been used in the treatment of male hypogonadism, delayed puberty in males, and in the treatment of breast neoplasms in women. [PubChem] Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anabolic Agent
  • Antineoplastic Agent, Hormonal
  • Drug
  • Ester
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-oneChEBI
17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesteroneChEBI
9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-oneChEBI
9alpha-Fluoro-11beta-hydroxy-17-methyltestosteroneChEBI
FluoximesteronaChEBI
FluoxymesteronumChEBI
AndroxyKegg
HalotestinKegg
11b,17b-Dihydroxy-9a-fluoro-17a-methyl-4-androster-3-oneGenerator
11Β,17β-dihydroxy-9α-fluoro-17α-methyl-4-androster-3-oneGenerator
17a-Methyl-9a-fluoro-11b-hydroxytesteroneGenerator
17Α-methyl-9α-fluoro-11β-hydroxytesteroneGenerator
9-Fluoro-11b,17b-dihydroxy-17-methylandrost-4-en-3-oneGenerator
9-Fluoro-11β,17β-dihydroxy-17-methylandrost-4-en-3-oneGenerator
9a-Fluoro-11b-hydroxy-17-methyltestosteroneGenerator
9Α-fluoro-11β-hydroxy-17-methyltestosteroneGenerator
AndrofluoreneHMDB
AndrofluoroneHMDB
FluossimesteroneHMDB
FluoximesteroneHMDB
FluoximesteronumHMDB
FluoxymestroneHMDB
FluoximesteronHMDB
Android-FHMDB
Android FHMDB
Atlantis brand OF fluoxymesteroneHMDB
Pharmacia brand OF fluoxymesteroneHMDB
StenoxHMDB
Chemical FormulaC20H29FO3
Average Molecular Mass336.441 g/mol
Monoisotopic Mass336.210 g/mol
CAS Registry Number76-43-7
IUPAC Name(1S,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
Traditional Namefluoxymesterone
SMILES[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1
InChI KeyYLRFCQOZQXIBAB-RBZZARIASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 9-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point265°C
Boiling PointNot Available
Solubility67.5 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.5ALOGPS
logP2.38ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.6ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.19 m³·mol⁻¹ChemAxon
Polarizability36.63 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1934000000-8eb342128d6bf9311319Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ou-0951400000-91106f5e4565733878feSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-48934627a15489915ee8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0289000000-97f81d1c3434cd2ebf78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3294000000-6727e66346d908d21d94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-8fa1a3bcb20d7e11f56cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0009000000-e763c698cec90ff489d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mo-0596000000-4dd2e6ac91164ea740ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-e06c0ac56f323c20416aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-2594000000-7ce7c92338e057214383Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ec-5940000000-063fa6a84fc098f79fcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-f77bab0fc5505f2a76bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029000000-47936a6dd33f48e53957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-2239000000-4e814ffc32e746f27d3fSpectrum
MSMass Spectrum (Electron Ionization)splash10-006x-5951000000-4c37d94fe4ed0b343941Spectrum
Toxicity Profile
Route of ExposureOral absorption is less than 44%.
Mechanism of ToxicityFluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.
MetabolismPresence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration. Inactivation of testosterone occurs primarily in the liver Half Life: 9.2 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIn males, used as replacement therapy in conditions associated with symptoms of deficiency or absence of endogenous testosterone. In females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSide effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01185
HMDB IDHMDB0015316
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluoxymesterone
Chemspider ID6205
ChEBI ID5120
PubChem Compound ID6446
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

U.S. Patent 2,793,218
U.S. Patent 2,813,881

MSDSLink
General References
1. Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM