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.
Progesterone is a hormone naturally produced in the body that plays key roles in the menstrual cycle, pregnancy, and the development of embryos, while also serving as a building block for producing other important hormones and supporting brain function. It belongs to a group of steroid hormones called progestogens and is the most abundant progestogen in the human body.
AI-generated from the Wikipedia summary — may 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
- Mass
- 314.225
Show 10 more facts
- Commons category
- Progesterone
- chemical formula
- C₂₁H₃₀O₂
- 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
- defined daily dose
- 5
- melting point
- 131.0
- partition coefficient water/octanol
- 3.87
- World Health Organisation international non-proprietary name
- 黄体酮
- density
- 1.116
- solubility
- 0.0206
Sources (11)
via Wikidata · CC0
~39 min read
Article
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.