Definition
ChEBI: Oxandrolone is a 3-oxo steroid, an oxa-steroid, a 17beta-hydroxy steroid and an anabolic androgenic steroid. It has a role as an androgen and an anabolic agent.
Manufacturing Process
To a solution of 6.36 parts of 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one in 95 parts of acetic acid and 12 parts of water is added 40 parts of lead tetracetate and 0.6 part of osmium tetroxide. This mixture is stored at room temperature for about 24 hours, then is treated with 2 parts of lead tetracetate. Evaporation to dryness at reduced pressure affords a residue, which is extracted with benzene. The benzene extract is washed with water, and extracted with aqueous potassium bicarbonate. The aqueous extract is washed with ether, acidified with dilute sulfuric acid, then extracted with ethyl
acetate-benzene. This organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness in vacuo. To a solution of the residual crude product in 20 parts of pyridine is added 10 parts of 20% aqueous sodium bisulfite and the mixture is stirred for about 20 minutes at room temperature
This mixture is then diluted with water, washed with ethyl acetate, acidified with dilute sulfuric acid, and finally extracted with benzene. The benzene extract is washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness at reduced pressure to produce crude 17β-hydroxy17α-methyl-1-oxo-1,2-seco-A-nor-5α-androstan-2-oic acid, which after recrystallization from aqueous isopropyl alcohol melts at about 166° to 173°C (decomposition).
An aqueous slurry of 6 parts of 17β-hydroxy-17α-methyl-1-oxo-1,2-seco-Anor-5α-androstan-2-oic acid in 200 parts of water is made alkaline to pH 10 by the addition of dilute aqueous sodium hydroxide, then is treated with 6 parts of sodium borohydride. This mixture is allowed to react at room temperature for about 3 hours. Benzene is added and the resulting mixture is acidified carefully with dilute hydrochloric acid. The benzene layer is separated, and the aqueous layer is further extracted with benzene. The combined benzene extracts are washed successively with aqueous potassium bicarbonate and water, dried over anhydrous sodium sulfate, then evaporated to dryness in vacuo. The resulting residue is triturated with ether to afford pure 17β-hydroxy-17α-methyl-2-oxa-5α-androstan-3-one, MP about 235° to 238°C, according to US Patent 3,128,283.
General Description
Oxandrolone, 17β-hydroxy-17-methyl-2-oxaandrostan-3-one, is approved to aid in the promotionof weight gain after weight loss following surgery,chronic infections, or severe trauma and to offset protein catabolismassociated with long-term corticosteroid use.Oxandrolone is also used to relieve bone pain accompanyingosteoporosis. It has been used to treat alcoholic hepatitisand HIV wasting syndrome.
Biochem/physiol Actions
Oxandrolone is a synthetic anabolic steroid. It is is a non-aromatizable androgen with no estrogenic effects and with mild androgenic activity. Clinical uses of oxandrolone include to promote weight gain after weight loss following extensive surgery or chronic infections or trauma, to offset the protein catabolism associated with prolonged administration of corticosteroids, to relieve bone pain frequently accompanying osteoporosis, and to treat Turner′s syndrome in girls.
Synthesis
Oxandrolone, 17|?-hydroxy-17|á-methyl-2-oxa-5-androstan-3-one (29.3.10),
is made by oxidation of the C1¨CC2 double bond of 17|?-hydroxy-17|á-methyl-1-androsten-
3-one by a mixture of lead tetraacetate and osmium tetroxide with an opening of the A ring
of the steroid system, which forms an aldehyde acid (29.3.9). Upon reducing the aldehyde
group with sodium borohydride, intramolecular cyclization takes place, directly forming a
lactone (29.3.10), which is the desired oxandrolone.
