Testosterone enanthate

Testosterone enanthate
Clinical data
Trade names	Delatestryl, Xyosted, others
Other names	TE; Testosterone heptanoate; Testosterone 17β-heptanoate; NSC-17591
Routes of; administration	Intramuscular injection, subcutaneous 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: high
Metabolism	Liver
Elimination half-life	Intramuscular: 4–5 days
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] heptanoate;
CAS Number	315-37-7;
PubChem CID	9416;
DrugBank	DB13944;
ChemSpider	9045;
UNII	7Z6522T8N9;
KEGG	D00958;
ChEBI	CHEBI:9464;
ChEMBL	ChEMBL1200335;
CompTox Dashboard (EPA)	DTXSID701016540 ;
ECHA InfoCard	100.005.686
Chemical and physical data
Formula	C26H40O3
Molar mass	400.603 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCC(=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/C26H40O3/c1-4-5-6-7-8-24(28)29-23-12-11-21-20-10-9-18-17-19(27)13-15-25(18,2)22(20)14-16-26(21,23)3/h17,20-23H,4-16H2,1-3H3/t20-,21-,22-,23-,25-,26-/m0/s1; Key:VOCBWIIFXDYGNZ-IXKNJLPQSA-N;

Testosterone enanthate is used in the treatment of low testosterone levels in men. It is also used in hormone therapy for women and transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

Side effects of testosterone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. 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 enanthate 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, which make it useful for producing masculinization and suitable for androgen replacement therapy. Esterase enzymes break the ester bond in testosterone enantate, releasing free testosterone and enanthic acid through hydrolysis. This process ensures a sustained release of testosterone in the body.

Testosterone enanthate was introduced for medical use in 1954. Along with testosterone cypionate, testosterone undecanoate, and testosterone propionate, it is one of the most widely used testosterone esters. In addition to its medical use, testosterone enanthate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.