Progesterone

Progesterone is a steroid hormone.

Progesterone

Names
IUPAC name (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Other names P4; Pregn-4-ene-3,20-dione[1][2]
Identifiers
CAS Number	57-83-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17026 Y
ChEMBL	ChEMBL103 Y
ChemSpider	5773 Y
DrugBank	DB00396 Y
ECHA InfoCard	100.000.318
KEGG	C00410 N
PubChem CID	5994
UNII	4G7DS2Q64Y Y
CompTox Dashboard (EPA)	DTXSID3022370
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
Properties
Chemical formula	C21H30O2
Molar mass	314.469 g/mol
Melting point	126
log P	4.04[3]
Pharmacology
ATC code	G03DA04 (WHO)
Routes of administration	By mouth, topical/transdermal, vaginal, intramuscular injection, subcutaneous injection, subcutaneous implant
Pharmacokinetics:
Bioavailability	OMP: <10%[4][5]
Protein binding	• Albumin: 80% • CBG: 18% • SHBG: <1% • Free: 1–2%[6][7]
Metabolism	Hepatic (CYP2C19, CYP3A4, CYP2C9, 5α-reductase, 3α-HSD, 17α-hydroxylase, 21-hydroxylase, 20α-HSD)[8][9]
Biological half-life	OMP: 16–18 hours[4][5][10] IM: 22–26 hours[5][11] SC: 13–18 hours[11]
Excretion	Renal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In animals, it is made from cholesterol. It is the base for certain estrogens and androgens. In animals, it is produced by their body mainly during the second half of the menstrual cycle.

During pregnancy it is produced in higher quantities. Willard Myron Allen co-discovered progesterone with George Washington Corner at the University of Rochester Medical School in 1933. Allen discovered the temperature needed to melt it and its weight. He also gave it the name "Progesterone" based on progestational steroidal ketone.^[12] In one plant, Juglans regia, progesterone has been found.^[13] Also progesterone-like steroids are found in Dioscorea mexicana.^[14] Progesterone level is low in children and postmenopausal women.^[15]

Biosynthesis

Steroidogenesis, showing progesterone among the progestogens in yellow area.^[16]

Related pages

• Steroid
• Oestrogen