Testosterone (medication)

Testosterone
Clinical data
Pronunciation	/tɛˈstɒstəroʊn/ teh-STOS-tə-rohn
Trade names	AndroGel, Testim, TestoGel, others
Other names	Androst-4-en-17β-ol-3-one
AHFS/Drugs.com	Monograph
MedlinePlus	a619028
License data	US DailyMed: Testosterone;
Pregnancy; category	AU: D; Contraindicated due to teratogenic effects;
Routes of; administration	By mouth, buccal, sublingual, intranasal, transdermal (gel, cream, patch, solution), vaginal (cream, gel, suppository), rectal (suppository), intramuscular or subcutaneous injection (oil solution, aqueous suspension), subcutaneous implant (pellet)
Drug class	Androgen, anabolic steroid
ATC code	G03BA03 (WHO) ;
Legal status
Legal status	AU: ; BR: Class C5 (Anabolic steroids); CA: Schedule IV; DE: ; NZ: ; UK: Class C; US: WARNINGSchedule III; UN: ; EU: Rx-only; Rx-only ;
Pharmacokinetic data
Bioavailability	Oral: very low (due to extensive first pass metabolism)
Protein binding	97.0–99.5% (to SHBGTooltip sex hormone-binding globulin and albumin)
Metabolism	Liver (mainly reduction and conjugation)
Elimination half-life	2–4 hours
Excretion	Urine (90%), feces (6%)
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;
CAS Number	58-22-0 ; 57-85-2 (propionate); 315-37-7 (enanthate); 58-20-8 (cypionate); 5949-44-0 (undecanoate);
PubChem CID	6013;
IUPHAR/BPS	2858;
DrugBank	DB00624 ;
ChemSpider	5791 ;
UNII	3XMK78S47O;
KEGG	D00075 ;
ChEBI	CHEBI:17347 ;
ChEMBL	ChEMBL386630 ;
Chemical and physical data
Formula	C19H28O2
Molar mass	288.431 g·mol−1
3D model (JSmol)	Interactive image;
Specific rotation	+110.2°
Melting point	155 °C (311 °F)
	SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4;
	InChI InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 ; Key:MUMGGOZAMZWBJJ-DYKIIFRCSA-N ;
	(verify)

Testosterone (T) is a medication and naturally occurring steroid hormone. It is used to treat male hypogonadism, gender dysphoria, and certain types of breast cancer. It may also be used to increase athletic ability in the form of doping. It is unclear if the use of testosterone for low levels due to aging is beneficial or harmful. Testosterone can be used as a gel or patch that is applied to the skin, injection into a muscle, tablet that is placed in the cheek, or tablet that is taken by mouth.

Common side effects of testosterone include acne, swelling, and breast enlargement in men. Serious side effects may include liver toxicity, heart disease, and behavioral changes. Women and children who are exposed may develop masculinization. It is recommended that individuals with prostate cancer should not use the medication. It can cause harm to the baby if used during pregnancy or breastfeeding. Testosterone is in the androgen family of medications.

Testosterone was first isolated in 1935, and approved for medical use in 1939. Rates of use have increased three times in the United States between 2001 and 2011. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 143rd most commonly prescribed medication in the United States, with more than 4 million prescriptions.

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