Originator
Depo-Testosterone,Upjohn,US,1951
Uses
Testosterone Cypionate is an anabolic steroid with androgenic properties. Testosterone Cypionate is used for testosterone therapy in males with hypogonadism.
Controlled Substance.
Definition
ChEBI: Testosterone cypionate is a sterol ester. It is functionally related to a 3-cyclopentylpropionic acid and a testosterone.
Manufacturing Process
1 g of crude 3-enol-ethyl ether of testosterone dissolved in 3 cc of pyridine is
treated with 2 cc of β-cyclopentylpropionic anhydride (obtained from the β-
cyclopentylpropionic acid and acetic anhydride: boiling point 180°C/2 mm Hg).
After standing at room temperature overnight the mixture is diluted with
water and extracted with ether, the ethereal layer, washed with water to
neutrality and dried, is evaporated by vacuum. The oily residue is taken up in
petroleum ether and filtered through a layer of aluminum oxide, which is
afterwards washed with a further amount of petroleum ether. The solution so
filtered and purified is evaporated to dryness; the crystalline residue is
recrystallized from a small amount of methanol containing a trace of pyridine:
about 1 g of 3-enol-ethyl-ether of the β-cyclopentyl propionate of
testosterone, melting point 86°C to 88°C, is so obtained (by further
recrystallization melting point 90°C to 91°C). This product (that may be
employed either in the crystalline state, or in the oily one, that is, before the
purification by filtration through aluminum oxide) by treatment with a small
amount of hydrochloric acid in acetone solution yields the β-cyclopentyl
propionate of testosterone, melting point 99°C to 101°C (recrystallized from
methanol).
Therapeutic Function
Androgen
Veterinary Drugs and Treatments
The use of injectable esters of testosterone in veterinary medicine is
limited primarily to its use in dogs (and perhaps cats) for the treatment
of testosterone-responsive urinary incontinence in neutered
males. Testosterone has been used to treat a rare form of dermatitis
(exhibited by bilateral alopecia) in neutered male dogs. These drugs
are also used in bovine medicine to produce an estrus-detector
(teaser) animal in cull cows, heifers, and steers.
The effectiveness of testosterone to increase libido, treat hypogonadism,
aspermia, and infertility in domestic animals has been disappointing.