Testosterone propionate

Testosterone propionate
Clinical data
Trade names	Testoviron, others
Other names	TP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166
Routes of; administration	Intramuscular injection, buccal
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	Intramuscular: 0.8 days (~20 hours)
Excretion	Urine
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] propanoate;
CAS Number	57-85-2;
PubChem CID	5995;
DrugBank	DB01420;
ChemSpider	5774;
UNII	WI93Z9138A;
KEGG	D00959;
ChEBI	CHEBI:9466;
ChEMBL	ChEMBL1170;
CompTox Dashboard (EPA)	DTXSID9036515 ;
ECHA InfoCard	100.000.319
Chemical and physical data
Formula	C22H32O3
Molar mass	344.495 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C;
	InChI InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1; Key:PDMMFKSKQVNJMI-BLQWBTBKSA-N;

Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been used to treat breast cancer in women. It is given by injection into muscle usually once every two to three days.

Side effects of testosterone propionate 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). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy. Testosterone propionate is a testosterone ester and a relatively short-acting prodrug of testosterone in the body. Because of this, it is considered to be a natural and bioidentical form of testosterone.

Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937. It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960. The introduction of longer-acting testosterone esters like testosterone enanthate, testosterone cypionate, and testosterone undecanoate starting in the 1950s resulted in testosterone propionate mostly being superseded. As such, it is rarely used today. In addition to its medical use, testosterone propionate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.

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