Fluoxymesterone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Fluoxymesterone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Fluoxymesterone?

The molecule Fluoxymesterone presents a molecular formula of C20H29FO3 and its IUPAC name is (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one.

Fluoxymesterone, also known as 9-alpha-fluoro-11-beta-hydroxy-17-alpha-methyl-4-androstadien-3-one, is a synthetic androstane steroid and a 17-alpha-alkylated derivative of testosterone. It was first described in 1956 and was introduced for medical use in 1964. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a potent androgen and has strong anabolic effects..

Fluoxymesterone is used in the treatment of hypogonadism and delayed puberty in males. It is also used in the treatment of breast cancer in women. The drug has also been used in the treatment of anemia and osteoporosis. Fluoxymesterone has been shown to be effective in the treatment of wasting in AIDS patients..

Fluoxymesterone is a white to pale yellow, crystalline powder. It is insoluble in water and slightly soluble in ethanol..

The chemical structure of fluoxymesterone is:.

Fluoxymesterone has a molecular weight of 336.44 and a molecular formula of C21H29FO3..

The drug is metabolized in the liver and is excreted in the urine..

Fluoxymesterone has a half-life of 9 hours..

The most common side effects of fluoxymesterone include:.

Fluoxymesterone is a controlled substance in the United States and lies as a Schedule III drug..

3D structure

Cartesian coordinates

Geometry of Fluoxymesterone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Fluoxymesterone YLRFCQOZQXIBAB-RBZZARIASA-N chemical compound 2D structure molecule svg
Fluoxymesterone

 

Molecule descriptors

 
IUPAC name(8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
InChI codeInChI=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
SMILESC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (11beta,17beta)-9-fluoro-11,17-dihydroxy-17-methylandrost-4-en-3-one
  • (1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-en-5-one
  • (8S,9R,10S,11S,13S,14S,17S)-9-fluoranyl-10,13,17-trimethyl-11,17-bis(oxidanyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
  • (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
  • (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
  • 010F480
  • 11-beta,17-beta-Dihydroxy-9-alpha-fluoro-17-alpha-methyl-4-androster-3-one
  • 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androsten-3-one
  • 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one
  • 17-alpha-Methyl-9-alpha-fluoro-11-beta-hydroxytesterone
  • 17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone
  • 76-43-7
  • 9-FLUORO-11.BETA.,17.BETA.-DIHYDROXY-17-METHYLANDROST-4-EN-3-ONE
  • 9-Fluoro-11-beta,17-beta-dihydroxy-17-methylandrost-4-en-3-one
  • 9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one
  • 9-alpha-Fluoro-11-beta,17-beta-dihydroxy-17-alpha-methyl-4-androstene-3-one
  • 9-alpha-Fluoro-11-beta-hydroxy-17-methyltestosterone
  • 9-alpha-Fluoro-17-alpha-methyl-11-beta,17-dihydroxy-4-androsten-3-one
  • 9-fluoro-11beta,17beta-dihydroxy-17alpha-methylandrost-4-en-3-one
  • 9.alpha.-Fluoro-11.beta.,17.beta.-dihydroxy-17.alpha.-methyl-4-androstene-3-one
  • 9.alpha.-Fluoro-11.beta.-hydroxy-17-methyltestosterone
  • 9JU12S4YFY
  • 9alpha-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one
  • 9alpha-Fluoro-11beta,17beta-dihydroxy-17alpha-methyl-4-androstene-3-one
  • 9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone
  • 9alpha-Fluoro-17alpha-methyl-11beta,17-dihydroxy-4-androsten-3-one
  • A838701
  • AC-29744
  • AI3-52940
  • Anadroid-F
  • Androfluorene
  • Androfluorone
  • Android-f
  • Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11.beta.,17.beta.)-
  • Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11beta,17beta)-
  • Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-
  • Androsterolo
  • Androxy
  • BCP10776
  • BDBM18189
  • BRN 2008796
  • CCRIS 9036
  • D00327
  • DB01185
  • DSSTox_CID_13512
  • DSSTox_GSID_33512
  • DSSTox_RID_79080
  • FXM
  • Fluoro-9-alpha dihydroxy-11-beta,17-beta methyl-17-alpha androstene-4 one-3
  • Fluossimesterone
  • Fluosterone
  • Fluotestin
  • Fluoximesterona
  • Fluoximesterone
  • Fluoximesteronum
  • Fluoxymesteron
  • Fluoxymesterone
  • Fluoxymesterone (JAN/USP/INN)
  • Fluoxymesterone 1.0 mg/ml in Acetonitrile
  • Fluoxymesterone ciii
  • Fluoxymesterone, solid (photosensitive)
  • Fluoxymesteronum
  • Fluoxymestrone
  • Flusteron
  • Flutestos
  • GTPL2861
  • HMS2272B06
  • HSDB 3333
  • Halotestin
  • LMST02020025
  • MLS001055414
  • NCGC00091037-01
  • NCGC00091037-02
  • NCGC00182970-01
  • NCGC00258408-01
  • NSC 10704
  • NSC-10704
  • NSC-12165
  • NSC10704
  • NSC12165
  • Neo-Ormonal
  • Ora Testryl
  • Ora-Testryl
  • Oralsterone
  • Oratestin
  • Q410663
  • SMR000686158
  • Testoral
  • Testosterone, 9-fluoro-11.beta.-hydroxy-17-methyl-
  • Testosterone, 9-fluoro-11beta-hydroxy-17-methyl-
  • U 6040
  • Ultandren
  • Ultandrene
  • W-104363
  • component of Halodrin
  • fluoxymesterone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3875484
  • CAS-76-43-7
  • UNII-9JU12S4YFY
  • AKOS015895109
  • DTXSID8033512
  • CHEMBL1445
  • CHEBI:5120
  • Tox21_113158
  • Tox21_200854
  • EINECS 200-961-8
  • SCHEMBL5096

Physico-Chemical properties

IUPAC name(8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
Molecular formulaC20H29FO3
Molecular weight336.441
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity91.45
LogP3.3
Topological polar surface area57.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.