Androstanolone

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

What is the Androstanolone?

The molecule Androstanolone presents a molecular formula of C19H30O2 and its IUPAC name is (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one.

Androstanolone, also known as 5α-dihydrotestosterone (DHT), is an androgen and anabolic steroid (AAS) which is used in the treatment of low testosterone levels, androgen deficiency, and breast cancer. It is a synthetic androstane steroid and a derivative of testosterone..

Androstanolone has strong androgenic effects and weak anabolic effects. It is a 5α-reduced steroid, and is a potent agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Androstanolone is a prodrug of DHT in the body, and has about 5 times the androgenic potency of testosterone and about 1/5th the anabolic potency of testosterone..

In addition to its AR agonist activity, androstanolone is also a potent 5α-reductase inhibitor, and can therefore decrease the levels of DHT in the body..

Androstanolone was first synthesized in 1935, and was used medically to treat androgen deficiency and breast cancer. It is no longer used medically, but remains popular as a black market AAS..

Androstanolone is a controlled substance in many countries, and is a Schedule III drug in the United States. It is a banned substance in competitive sports, and use can result in a positive drug test..

3D structure

Cartesian coordinates

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

2D drawing

 

Androstanolone NVKAWKQGWWIWPM-ABEVXSGRSA-N chemical compound 2D structure molecule svg
Androstanolone

 

Molecule descriptors

 
IUPAC name(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyNVKAWKQGWWIWPM-ABEVXSGRSA-N
SMILESC[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O

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.

  • (+)-Androstan-17.beta.-ol-3-one
  • (+)-Androstan-17beta-ol-3-one
  • (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadecan-5-one
  • (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
  • (5-alpha,17-beta)-17-Hydroxyandrostan-3-one
  • (5.alpha.,17.beta.)-17-Hydroxy-androstan-3-one
  • (5S,8R,10S,13S,17S)-17-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
  • (5alpha,17beta)-17-hydroxyandrostan-3-one
  • 08J2K08A3Y
  • 17-.beta.-Hydroxy-5-.alpha.-androstan-3-one
  • 17-Hydroxy-androstan-3-one
  • 17-Hydroxyandrostan-3-one
  • 17-Hydroxyandrostan-3-one, (5.alpha.,17.beta.)- #
  • 17-beta-Hydroxy-5-alpha-androstan-3-one
  • 17-beta-hydroxyandrostan-3-one
  • 17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16, 17-hexadecahydrocyclopenta[a]phenanthren-3-one
  • 17.BETA.-HYDROXY-5.ALPHA.-ANDROSTAN-3-ONE
  • 17.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE-3-ONE
  • 17.beta.-Hydroxy-3-androstanone
  • 17b-Hydroxy-3-androstanone
  • 17beta-Hydroxy-3-androstanone
  • 17beta-Hydroxy-5alpha-androstan-3-one
  • 17beta-Hydroxy-5alpha-androstane-3-one
  • 17beta-Hydroxy-androstan-3-one
  • 17beta-Hydroxyandrostan-3-one
  • 17beta-hydroxy-3-oxo-5alpha-androstanone
  • 1d2s
  • 1kdk
  • 1t5z
  • 1t63
  • 1t7r
  • 2ama
  • 4,5-alpha-Dihydrotestosterone
  • 4,5.alpha.-Dihydrotestosterone
  • 4,5a-Dihydrotestosterone
  • 4,5alpha-Dihydrotestosterone
  • 4-Dihydrotestosterone
  • 5-.alpha.-Androstanolone
  • 5-a-Androstanolone
  • 5-alpha-Androstan-17-beta-ol-3-one
  • 5-alpha-Androstan-3-one, 17-beta-hydroxy-
  • 5-alpha-Androstanolone
  • 5-alpha-Dihydrotestosterone
  • 5.alpha.,17.beta.-Hydroxyandrostan-3-one
  • 5.alpha.-Androstan-17.beta.-ol-3-one
  • 5.alpha.-Androstan-3-one, 17.beta.-hydroxy-
  • 5.alpha.-Dihydrotestosterone
  • 5.alpha.-Dihydroxytestosterone
  • 521-18-6
  • 521-18-6 (free)
  • 521S186
  • 5A-Androstan-3-on-17B-ol
  • 5B-Androstan-3-on-17B-ol
  • 5a-Androstan-17b-ol-3-one
  • 5a-Dihydrotestosterone
  • 5alpha dihydrotestosterone
  • 5alpha,17beta-Hydroxyandrostan-3-one
  • 5alpha,17eta-Hydroxyandrostan-3-one
  • 5alpha-Androstan-17beta-ol-3-one
  • 5alpha-Androstan-3-one, 17beta-hydroxy-
  • 5alpha-Androstanolone
  • 5alpha-DHT
  • 5alpha-Dihydrotestosterone
  • 5alpha-Dihydroxytestosterone
  • 5alpha-dihydrotesosterone
  • AC-16144
  • AC-33095
  • AMY22298
  • Anaboleen
  • Anabolex
  • Andractim
  • Andrin
  • Androlone
  • Androstan-17.beta.-ol-3-one
  • Androstan-17b-ol-3-one
  • Androstan-17beta-ol-3-one
  • Androstan-3-one, 17-hydroxy-, (5.alpha.,17.beta.)-
  • Androstan-3-one, 17-hydroxy-, (5a,17b)-
  • Androstan-3-one, 17-hydroxy-, (5alpha,17beta)-
  • Androstanolona
  • Androstanolone
  • Androstanolone (5alpha-Dihydrotestosterone; Stanolone)
  • Androstanolone (5alpha-Dihydrotestosterone; Stanolone) 1.0 mg/ml in Acetonitrile
  • Androstanolone (INN)
  • Androstanolonum
  • BDBM18161
  • BDBM50366473
  • BIDD:ER0136
  • BIDD:PXR0075
  • C03917
  • CCG-267385
  • CS-5096
  • Cristerona MB
  • D07456
  • DB02901
  • DHT
  • DSSTox_CID_2364
  • DSSTox_GSID_22364
  • DSSTox_RID_76558
  • Dihydrotestosteron
  • EC 208-307-3
  • Epitope ID:135868
  • GS-6587
  • GTPL2856
  • GTPL3455
  • HMS2272H05
  • HY-A0120
  • LMST02020042
  • MLS001304063
  • NCGC00091013-01
  • NCGC00091013-02
  • NCGC00091013-03
  • NCGC00257456-01
  • NCGC00258540-01
  • NSC 10972
  • NSC-10972
  • NSC10972
  • Neodrol
  • Proteina
  • Protona
  • Q411054
  • SMR000058342
  • STANOLONE
  • Stanaprol
  • Stanolon
  • Stanorone
  • Testosterone, dihydro-
  • [3H]-dihydrotestosterone
  • [3H]DHT
  • [3H]dihydrotestosterone
  • dihydrotestosterone
  • dihydrotestosterone (dht)
  • s4757

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3814360
  • CAS-521-18-6
  • UNII-08J2K08A3Y
  • AKOS015894892
  • DTXSID9022364
  • CHEMBL27769
  • CHEBI:16330
  • Tox21_111056
  • Tox21_200987
  • Tox21_303655
  • EINECS 208-307-3
  • SCHEMBL15163

Physico-Chemical properties

IUPAC name(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Molecular formulaC19H30O2
Molecular weight290.44
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity85.83
LogP4.0
Topological polar surface area37.3

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.