Testosterone

Testosterone
Names


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
Other names Androst-4-en-17β-ol-3-one
Identifiers
CAS Number	58-22-0^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17347^Y
ChEMBL	ChEMBL386630^Y
ChemSpider	5791^Y
DrugBank	DB00624^Y
ECHA InfoCard	100.000.336
KEGG	D00075^Y
PubChem	6013
UNII	3XMK78S47O^Y
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
SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
Chemical formula	C₁₉H₂₈O₂
Molar mass	288.42 g/mol
Melting point	155
Pharmacology
ATC code	G03BA03 (WHO)
Routes of administration	Transdermal (gel, cream, solution, patch), by mouth (as testosterone undecanoate), in the cheek, intranasal (gel), intramuscular injection (as esters), subcutaneous pellets
Pharmacokinetics:
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%)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Testosterone is the primary male sex hormone and an anabolic steroid. In men, testosterone plays a key role in the development of male reproductive tissues such as the testis and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. In addition, testosterone is essential for health and well-being, and for the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty and bone loss.

Testosterone is also used as a medication to treat male hypogonadism and certain types of breast cancer. Since testosterone levels gradually decrease as men age, synthetic testosterone is sometimes prescribed to older men to counteract this deficiency.

Testosterone is a steroid from the androstane class containing a keto and hydroxyl groups at the three and seventeen positions respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor.

In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. Small amounts are also secreted by the adrenal glands. On average, in adult males, levels of testosterone are about 7–8 times as great as in adult females. As the metabolic consumption of testosterone in males is greater, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone.

...
Wikipedia