Testosterone (medication)

Testosterone (medication)

Clinical data
Pronunciation	tess-toss-ter-own
Trade names	Androgel, Testim, Testogel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a614041
License data	EU EMA: Intrinsa US FDA: Testosterone
Pregnancy category	US: X (Contraindicated) Contraindicated due to teratogenic effects
Routes of administration	Transdermal (gel, cream, solution, patch), by mouth (as testosterone undecanoate), in the cheek, intranasal (gel), intramuscular injection (as esters), subcutaneous pellets
ATC code	G03BA03 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Oral: very low (due to extensive first pass metabolism)
Protein binding	97.0–99.5% (to SHBG and albumin)
Metabolism	Liver (mainly reduction and conjugation)
Biological 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
Synonyms	Androst-4-en-17β-ol-3-one
CAS Number	58-22-0 Y
PubChem CID	6013
IUPHAR/BPS	2858
DrugBank	DB00624 Y
ChemSpider	5791 Y
UNII	3XMK78S47O
KEGG	D00075 Y
ChEBI	CHEBI:17347 Y
ChEMBL	CHEMBL386630 Y
Chemical and physical data
Formula	C19H28O2
Molar mass	288.42 g/mol
3D model (Jmol)	Interactive image
Specific rotation	+110.2°
Melting point	155 °C (311 °F)
SEC combustion	−11080 kJ/mol
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 Y Key:MUMGGOZAMZWBJJ-DYKIIFRCSA-N Y

Testosterone is a medication and naturally occurring steroid hormone. It is used to treat male hypogonadism 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 from testosterone medication include acne, swelling, and breast enlargement in males. Serious side effects may include liver toxicity, heart disease, and behavioral changes. Women and children who are exposed may develop virilization. It is recommended that individuals with prostate cancer not use the medication. It can cause harm to the baby if used during pregnancy or breastfeeding.

Testosterone was first isolated in 1935. 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, the most effective and safe medicines needed in a health system. It is available as a generic medication. The price depends on the dose and form of the product.