Chemical Properties
White Solid
Usage
Anabolic steroid. Androgen.
Controlled substance.
Usage
androgen
anabolic steroid
Uses
Anabolic steroid. Androgen.
Controlled substance.
Uses
androgen
anabolic steroid
Definition
ChEBI: An organic heteropentacyclic compound resulting from the formal condensation of the 3-keto-aldehyde moiety of oxymetholone with hydrazine. Like oxymetholone, it is a synthetic anabolic steroid. It has both anabolic and androgenic properties, and has been u
ed to treat hereditary angioedema and various vascular disorders. It has also been widely abused by professional athletes.
Originator
Winstrol,Winthrop,US,1961
Manufacturing Process
To a stirred solution of 1.00 gram of 17β-hydroxy-17α-methyl-4-
androsteno[3,2-c]pyrazole in 200 ml of tetrahydrofuran and 400 ml of liquid
ammonia was added 2.12 grams of lithium wire during 5 minutes. The dark
blue mixture was stirred for 45 minutes. A solution of 40 ml of tertiary-butyl
alcohol in 160 ml of diethyl ether was added with stirring.
After 15 minutes, 25 ml of ethanol was added with stirring. The mixture
turned colorless after several hours, and the liquid ammonia was allowed to
evaporate and the mixture was allowed to warm to room temperature over a
period of about 15 hours.
The solvent was evaporated to yield a colorless solid residue, which was taken
up in ethyl acetate-ice water. The two layers were separated and the aqueous
layer was extracted with ethyl acetate. The combined organic layers were
washed with water, saturated sodium chloride solution and filtered through
anhydrous sodium sulfate. The solvent was evaporated to yield 1.20 grams of
light tan crystals, MP 151° to 155°C, ultraviolet maximum at 224 mμ (E =
4,095). Two recrystallizations from ethanol afforded: 1st crop, 0.619 grams
(62%) of colorless crystals (dried at 120°C in vacuo for 17 hours), MP 232.8°
to 238.0°C, ultraviolet maximum at 224 mμ (E = 4,840); 2nd crop, 0.142
gram (14%) of colorless crystals, MP 234° to 242°C.
Brand name
Winstrol (Ovation).
Therapeutic Function
Anabolic
Synthesis
Stanozol, 17|á-methyl-5|á-androstano[3,2-c]pyrazol-17|?-ol (29.3.13), is made
by reducing the double bond at C4¨CC5 in methyltestosterone, which has independent interest as an anabolic drug of mestanolone (29.3.11). Mestanolone undergoes formylation
with ethylformate in the presence of sodium ethoxide, forming a 2-formyl (oxymethylene)
derivative (29.3.12), which upon reaction with hydrazine easily cyclizes to the desired
stanazole (29.3.13), which is a pyrazol-condensed steroid system.
Veterinary Drugs and Treatments
Labeled indications for the previously marketed veterinary stanozolol
product Winstrol?-V (Winthrop/Upjohn) included “…to
improve appetite, promote weight gain, and increase strength and
vitality…” in dogs, cats and horses. The manufacturer also stated
that: “Anabolic therapy is intended primarily as an adjunct to other
specific and supportive therapy, including nutritional therapy.”
Like nandrolone, stanozolol has been used to treat anemia of
chronic disease. Because stanozolol has been demonstrated to enhance
fibrinolysis after parenteral injection, it may be efficacious
in the treatment of feline aortic thromboembolism or thrombosis
in nephrotic syndrome; however, clinical studies and/or experience
are apparently lacking for this indication at present.
