Progesterone

Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the major progestogen in the body. Progesterone has a variety of important functions in the body. It is also a crucial metabolic intermediate in the production of other endogenous steroids, including the sex hormones and the corticosteroids, and plays an important role in brain function as a neurosteroid.

This article is about progesterone as a hormone. For its use as a medication, see progesterone (medication).
Progesterone
Names
IUPAC name
Pregn-4-ene-3,20-dione
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
P4; Pregnenedione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.318
KEGG
UNII
  • InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 N
    Key: RJKFOVLPORLFTN-LEKSSAKUSA-N Y
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
Properties
C21H30O2
Molar mass 314.469 g/mol
Melting point 126
log P 4.04
Pharmacology
G03DA04 (WHO)
By mouth, topical/transdermal, vaginal, intramuscular injection, subcutaneous injection, subcutaneous implant
Pharmacokinetics:
OMP: <10%
• Albumin: 80%
• CBG: 18%
• SHBG: <1%
• Free: 1–2%
Hepatic (CYP2C19, CYP3A4, CYP2C9, 5α-reductase, 3α-HSDTooltip 3α-hydroxysteroid dehydrogenase, 17α-hydroxylase, 21-hydroxylase, 20α-HSDTooltip 20α-hydroxysteroid dehydrogenase)
OMP: 16–18 hours
IM: 22–26 hours
SC: 13–18 hours
Renal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

In addition to its role as a natural hormone, progesterone is also used as a medication, such as in combination with estrogen for contraception, to reduce the risk of uterine or cervical cancer, in hormone replacement therapy, and in feminizing hormone therapy. It was first prescribed in 1934.

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