Testosterone cypionate

Testosterone cypionate
Clinical data
Trade names	Depo-Testosterone, others
Other names	TC; TCPP; Testosterone cipionate; Testosterone cyclopentylpropionate; Testosterone cyclopentanepropionate; Testosterone 17β-cyclopentylpropionate
Routes of; administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester
Legal status
Legal status	CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Bioavailability	Oral: very low; Intramuscular: very high
Metabolism	Liver
Elimination half-life	~8 days i.m.Tooltip intramuscular injection)
Excretion	90% Urine; 6% feces
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate;
CAS Number	58-20-8;
PubChem CID	441404;
DrugBank	DB13943;
ChemSpider	390140;
UNII	M0XW1UBI14;
KEGG	D00957;
ChEMBL	ChEMBL1201101;
CompTox Dashboard (EPA)	DTXSID901015617 ;
ECHA InfoCard	100.000.335
Chemical and physical data
Formula	C27H40O3
Molar mass	412.614 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C;
	InChI InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1; Key:HPFVBGJFAYZEBE-ZLQWOROUSA-N;

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men, including hormone therapy for transgender men. It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.

Side effects of testosterone cypionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. Testosterone supplementation is also known to reduce the threshold for aggressive behavior in men. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Testosterone cypionate is converted by the body to testosterone that has both androgenic effects and anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy; still, the relative potency of these effects can depend on various factors and is a topic of ongoing research. Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into DHT or aromatized to estradiol (E2). Both testosterone and DHT bind to an androgen receptor; however, DHT has a stronger binding affinity than testosterone and may have more androgenic effect in certain tissues at lower levels. Testosterone cypionate is a testosterone ester and a long-lasting prodrug of testosterone in the body. Because of this, it is considered to be a natural and bioidentical form of testosterone.

Testosterone cypionate was introduced for medical use in 1951. Along with testosterone enanthate, testosterone undecanoate, and testosterone propionate, it is one of the most commonly used testosterone esters. It is used mainly in the United States. In addition to its medical use, testosterone cypionate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.