Oxandrolone

Chemical Name 17(3-hydroxy-17-methyl-2-oxa-5a-androstan-3-one Common Name — 

Trade Name Manufacturer Country Year Introduced 

17 -Hydroxy-17fll-methyl-5tt-androst-1 -en-3-one Lead tetraacetate Sodium borohydride 

To a solution of 6.36 parts of 17(3-hydroxy-17a-methyl-5o -androst-Ten-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 

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Conjugate addition of methyl magnesium iodide in the presence of cuprous chloride to the enone (91) leads to the la-methyl product mesterolone (92) Although this is the thermodynamically unfavored axially disposed product, no possibility for isomerization exists in this case, since the ketone is once removed from this center. In an interesting synthesis of an oxa steroid, the enone (91) is first oxidized with lead tetraacetate the carbon at the 2 position is lost, affording the acid aldehyde. Reduction of this intermediate, also shown in the lactol form, with sodium borohydride affords the steroid lactone oxandrolone... 

Oxandrolone Oxandrolone, 17j3-hydroxy-17a-methyl-2-oxa-5-androstan-3-one (29.3.10), is made by oxidation of the C1-C2 double bond of 17j3-hydroxy-17a-methyl-l-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 [31,32]. 

Oxandrolone is used for the same indications as nandrolone. Synonyms of this drug are vasorome, anavar, and others. 

Deca-Durabolin), methandrostenolone Dianabot), oxymetholone (Anadrol, Adroyd),stanozolol (Winstrol), and oxandrolone (Anavar). 

Contraindications Nephrosis, carcinoma of breast or prostate hypercalcemia, hypersensitivity to oxandrolone or any component of the formulation... 

Testosterone (5.45) is the prototypic androgen sex hormone. Testosterone is synthesized by the testes, and must be reduced to dihydrotestosterone (5.46, DHT) before it will bind to the receptor. Among highly active synthetic testosterone analogs, 7a-methyl-19-nortestosterone (5.47) and oxandrolone (5.48) have about 100 times greater activity than testosterone as androgens. 17a-Methyltestosterone (5.49) is orally active. 

AAS are Schedule 111 drugs and are referred to as roids and juice. Products include Anadrol (oxymetholone), Oxan-drin (oxandrolone), Dianabol (methandrostenolone, D-bol, D-ball), Winstrol (stanozolol), Durabolin (nandrolone), Depo -testosterone (testosterone, Depo-T), and Equipoise (boldenone). 

While opinions are many and varied, only a few groups have made an adequate effort to acquire firm data on relative benefits and harms. In a randomized study using the anabolic androgen oxandrolone, 32 men aged 60-87... 

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