پروژسترون

Also known as 17alpha-progesterone, luteohormone, corpus luteum hormone, (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, (8S,9S,10R,13S,14S,17S)-17-ethanoyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one, (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one, 17α-progesterone, delta(4)-pregnene-3,20-dione

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.

OverviewAI-generated

Progesterone is a chemical compound with the formula C₂₁H₃₀O₂. Its IUPAC name is (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. The substance has a molecular weight of 314.5 and a mass of 314.225. It features a density of 1.116 and a melting point of 131.0. The partition coefficient for water and octanol is 3.87, while the xlogp value is 3.9. Solubility is recorded at 0.0206.

The compound has a defined daily dose of 5. It contains zero hydrogen bond donors and two hydrogen bond acceptors, with a topological polar surface area of 34.1. The molecule carries a charge of 0. In scientific literature, progesterone is the subject of 137,525 PubMed entries. Additionally, it is referenced by 2,895 other encyclopedia articles.

Synthesized by Vinony from 23 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C21H30O2
Molecular weight: 314.5 g/mol
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
SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChIKey: RJKFOVLPORLFTN-LEKSSAKUSA-N
XLogP: 3.9
Polar surface area: 34.1 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1976
Admin. routes: oral, parenteral, topical
Indications: infertility, premature birth, cocaine dependence, nicotine dependence

via ChEMBL · EBI

Research

137,525 papers

Progesterone and abnormal uterine bleeding/menstrual disorders.ReviewBest practice & research. Clinical obstetrics & gynaecology · 2020Jewson M, Purohit P, Lumsden MADOI: 10.1016/j.bpobgyn.2020.05.004
Progesterone modulates neuronal excitability bidirectionally.ReviewNeuroscience letters · 2021Kapur J, Joshi SDOI: 10.1016/j.neulet.2020.135619
Progesterone, reproduction, and psychiatric illness.ReviewBest practice & research. Clinical obstetrics & gynaecology · 2020Standeven LR, McEvoy KO, Osborne LMDOI: 10.1016/j.bpobgyn.2020.06.001
Progesterone and neuroprotection.ReviewHormones and behavior · 2013Singh M, Su CDOI: 10.1016/j.yhbeh.2012.06.003
Progesterone for the prevention and treatment of osteoporosis in women.ReviewClimacteric : the journal of the International Menopause Society · 2018Prior JCDOI: 10.1080/13697137.2018.1467400
Progesterone withdrawal: key to parturition.ReviewAmerican journal of obstetrics and gynecology · 2007Zakar T, Hertelendy FDOI: 10.1016/j.ajog.2006.09.005
Progesterone-mediated immunomodulation in ruminant early pregnancy: mechanisms and implications for bovine fertility.ReviewVeterinary research communications · 2025Batool I, Kausar R, Qamar MSDOI: 10.1007/s11259-025-10963-x
Progesterone: therapeutic opportunities for neuroprotection and myelin repair.ReviewPharmacology & therapeutics · 2007Schumacher M, Guennoun R, Stein DG et al.DOI: 10.1016/j.pharmthera.2007.06.001

via PubMed

Wikidata facts

Has part: carbon
Mass: 314.225
Has use: medication

Show 14 more facts

Commons category: Progesterone
chemical formula: C₂₁H₃₀O₂
medical condition treated: endometrial hyperplasia
canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
subject has role: primary metabolite
defined daily dose: 5
melting point: 131.0
partition coefficient water/octanol: 3.87
has characteristic: bitterness
legal status (medicine): boxed warning
World Health Organisation international non-proprietary name: 黄体酮
density: 1.116
solubility: 0.0206