Oxandrolone

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

What is the Oxandrolone?

The molecule Oxandrolone presents a molecular formula of C19H30O3 and its IUPAC name is (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one.

Oxandrolone is a synthetic anabolic steroid that was first developed in 1964 by Raphael Pappo while working at Searle Laboratories. It is known by the brand names Anavar and Oxandrin. Oxandrolone is considered to be a relatively safe and mild anabolic steroid when compared to other anabolic steroids. It is most often used to help people gain weight after a significant weight loss due to illness or injury. It is also used to help offset the protein catabolism that often accompanies long-term corticosteroid therapy..

3D structure

Cartesian coordinates

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

2D drawing

 

Oxandrolone QSLJIVKCVHQPLV-PEMPUTJUSA-N chemical compound 2D structure molecule svg
Oxandrolone

 

Molecule descriptors

 
IUPAC name(1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
InChI codeInChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
InChI KeyQSLJIVKCVHQPLV-PEMPUTJUSA-N
SMILESC[C@]12COC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O

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.

  • (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
  • (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
  • (4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-hydroxy-4a,6a,7-trimethyltetradecahydroindeno[4,5-h]isochromen-2(1H)-one
  • 17-beta-hydroxy-17-methyl-2-oxa-androstan-3-one
  • 17.beta.-Hydroxy-17-methyl-2-oxa-5.alpha.-androstan-3-one
  • 17alpha-Methyl-17beta-hydroxy-2-oxa-5alpha-androstan-3-one
  • 17beta-Hydroxy-17-methyl-2-oxa-5alpha-androstan-3-one
  • 17beta-Hydroxy-17alpha-methyl-2-oxa-5alpha-androstan-3-one
  • 198O944
  • 2-Oxa-5-alpha-androstan-3-one, 17-beta-hydroxy-17-methyl-
  • 2-Oxa-5alpha-androstan-3-one, 17beta-hydroxy-17-methyl-
  • 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5-alpha,17-beta)-
  • 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5.alpha.,17.beta.)-
  • 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5alpha,17beta)-
  • 53-39-4
  • 7H6TM3CT4L
  • 8075 C. B.
  • 8075 C.B.
  • 8075 CB
  • AB01559948-01
  • AC-14975
  • Anavar
  • C07346
  • CCG-220110
  • D00462
  • DB00621
  • Dodecahydro-3-hydroxy-6-(hydroxy-methyl)-3,3a,6-trimethyl-1H-benz(e)indene-7-acetic acid delta-lactone
  • GTPL7092
  • HMS3712E22
  • HSDB 3373
  • HY-B0707
  • Lonavar
  • NSC 67068
  • NSC-67068
  • OXANDROLONE
  • Ossandrolone
  • Oxandrin
  • Oxandrin;Anavar
  • Oxandrolona
  • Oxandrolone
  • Oxandrolone (JAN/USP/INN)
  • Oxandrolone ciii
  • Oxandrolonum
  • Protivar
  • Provitar
  • Q420859
  • SC 11585
  • SC-11585
  • SR-01000872645
  • SR-01000872645-1
  • Vasorome
  • W-105740

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3813047
  • UNII-7H6TM3CT4L
  • AKOS025401400
  • DTXSID8023399
  • CHEMBL1200436
  • CHEBI:7820
  • EINECS 200-172-9
  • SCHEMBL148881

Physico-Chemical properties

IUPAC name(1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
Molecular formulaC19H30O3
Molecular weight306.44
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity86.96
LogP3.5
Topological polar surface area46.5

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.