Progesterone

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 Pregn-4-ene-3,20-dione
Identifiers
CAS Number	57-83-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17026 Y
ChEMBL	ChEMBL103 Y
ChemSpider	5773 Y
DrugBank	DB00396 Y
ECHA InfoCard	100.000.318
KEGG	C00410 N
PubChem	5994
UNII	4G7DS2Q64Y Y
InChI 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
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	314.46 g/mol
Melting point	126
Pharmacology
ATC code	G03DA04 (WHO)
Routes of administration	By mouth, topical/transdermal, vaginal, intramuscular injection, subcutaneous injection, subcutaneous implant
Pharmacokinetics:
Bioavailability	OMP: <10%
Protein binding	• Albumin: 80% • CBG: 18% • SHBG: <1% • Free: 1–2%
Metabolism	Hepatic (CYP2C19, CYP3A4, CYP2C9, 5α-reductase, 3α-HSD, 17α-hydroxylase, 21-hydroxylase, 20α-HSD)
Biological half-life	OMP: 16–18 hours IM: 22–26 hours SC: 13–18 hours
Excretion	Renal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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 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.

Progesterone is the most important progestogen in the body, the result of its action as a potent agonist of the nuclear progesterone receptor (nPR) (with an affinity of K_D = 1 nM). In addition, progesterone is an agonist of the more recently discovered membrane progesterone receptors (mPRs), as well as a ligand of the PGRMC1 (progesterone receptor membrane component 1; formerly known as the σ₂ receptor). Moreover, progesterone is also known to be an antagonist of the σ₁ receptor, a negative allosteric modulator of the nACh receptors, and a potent antagonist of the mineralocorticoid receptor (MR). Progesterone prevents MR activation by binding to this receptor with an affinity exceeding even those of aldosterone and glucocorticoids such as cortisol and corticosterone, and produces antimineralocorticoid effects, such as natriuresis, at physiological concentrations. In addition, progesterone binds to and behaves as a partial agonist of the glucocorticoid receptor (GR), albeit with very low potency (EC₅₀ >100-fold less relative to cortisol).