File:Progesterone.svg · Wikimedia Commons · See Wikimedia Commons
progesterone
Sign in to saveAlso 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 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
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
Sources (11)
via Wikidata · CC0
~39 min read
Encyclopedic overview
39 sectionsContents
- Biological activity
- Biological function
- Hormonal interactions
- Early sexual differentiation
- Reproductive system
- Breasts
- Lobuloalveolar development
- Ductal development
- Breast cancer risk
- Skin health
- Sexuality
- Libido
- Homosexuality
- Nervous system
- Brain damage
- Proposed mechanism
- Addiction
- Societal
- Other effects
- Biochemistry
- Biosynthesis
- Distribution
- Metabolism
- Levels
- Ranges
- Sources
- Animal
- Plants
- Medical use
- Chemistry
- Synthesis
- Marker semisynthesis
- Soy semisynthesis
- Total synthesis
- History
- Veterinary use
- Pricing
- References
- External links
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.
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.
Excerpted from Wikipedia’s “progesterone” article, available under the CC BY-SA 4.0 licence.