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Progesterone

This article is about progesterone as a hormone. For its use as a medication, see progesterone (medication).
Progesterone
The chemical structure of progesterone.
A ball-and-stick model of progesterone.
Names
IUPAC name
Pregn-4-ene-3,20-dione[2][3]
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;[1] Pregnenedione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.318 Edit this at Wikidata
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 checkY
  • 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[4]
Pharmacology
G03DA04 (WHO)
By mouth, topical/transdermal, vaginal, intramuscular injection, subcutaneous injection, subcutaneous implant
Pharmacokinetics:
OMP: <10%[5][6]
• Albumin: 80%
• CBG: 18%
• SHBG: <1%
• Free: 1–2%[7][8]
Hepatic (CYP2C19, CYP3A4, CYP2C9, 5α-reductase, 3α-HSDTooltip 3α-hydroxysteroid dehydrogenase, 17α-hydroxylase, 21-hydroxylase, 20α-HSDTooltip 20α-hydroxysteroid dehydrogenase)[9][10]
OMP: 16–18 hours[5][6][11]
IM: 22–26 hours[6][12]
SC: 13–18 hours[12]
Renal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species.[1][13] It belongs to a group of steroid hormones called the progestogens[13] 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.[14]

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.[15] It was first prescribed in 1934.[16]

  1. ^ a b Cite error: The named reference James2015 was invoked but never defined (see the help page).
  2. ^ Adler N, Pfaff D, Goy RW (6 December 2012). Handbook of Behavioral Neurobiology Volume 7 Reproduction (1st ed.). New York: Plenum Press. p. 189. ISBN 978-1-4684-4834-4. Archived from the original on 14 January 2023. Retrieved 4 July 2015.
  3. ^ "progesterone (CHEBI:17026)". ChEBI. European Molecular Biology Laboratory-EBI. Archived from the original on 20 March 2016. Retrieved 4 July 2015.
  4. ^ "Progesterone_msds". Archived from the original on 12 February 2021. Retrieved 19 April 2018.
  5. ^ a b Cite error: The named reference pmid12215716 was invoked but never defined (see the help page).
  6. ^ a b c Cite error: The named reference pmid8513955 was invoked but never defined (see the help page).
  7. ^ Fritz MA, Speroff L (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 44–. ISBN 978-1-4511-4847-3.
  8. ^ Marshall WJ, Bangert SK (2008). Clinical Chemistry. Elsevier Health Sciences. pp. 192–. ISBN 978-0-7234-3455-9. Archived from the original on 14 January 2023. Retrieved 5 October 2016.
  9. ^ Yamazaki H, Shimada T (October 1997). "Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes". Archives of Biochemistry and Biophysics. 346 (1): 161–169. doi:10.1006/abbi.1997.0302. PMID 9328296.
  10. ^ McKay GA, Walters MR (6 February 2013). Lecture Notes: Clinical Pharmacology and Therapeutics. John Wiley & Sons. p. 33. ISBN 978-1-118-34489-7. Archived from the original on 14 January 2023. Retrieved 27 June 2015.
  11. ^ Zutshi V, Rathore AM, Sharma K (1 January 2005). Hormones in Obstetrics and Gynaecology. Jaypee Brothers Publishers. p. 74. ISBN 978-81-8061-427-9.[permanent dead link]
  12. ^ a b Cometti B (November 2015). "Pharmaceutical and clinical development of a novel progesterone formulation". Acta Obstetricia et Gynecologica Scandinavica. 94 (Suppl 161): 28–37. doi:10.1111/aogs.12765. PMID 26342177. S2CID 31974637.
  13. ^ a b Cite error: The named reference KingBrucker2010 was invoked but never defined (see the help page).
  14. ^ Baulieu E, Schumacher M (2000). "Progesterone as a neuroactive neurosteroid, with special reference to the effect of progesterone on myelination". Steroids. 65 (10–11): 605–612. doi:10.1016/s0039-128x(00)00173-2. PMID 11108866. S2CID 14952168.
  15. ^ Prior JC (April 2019). "Progesterone Is Important for Transgender Women's Therapy-Applying Evidence for the Benefits of Progesterone in Ciswomen". The Journal of Clinical Endocrinology and Metabolism. 104 (4): 1181–1186. doi:10.1210/jc.2018-01777. PMID 30608551. S2CID 58620122. Evidence has accrued that normal progesterone (and ovulation), as well as physiological estradiol levels, is necessary during ciswomen's premenopausal menstrual cycles for current fertility and long-term health; transgender women may require progesterone therapy and similar potential physiological benefits
  16. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 47X. ISBN 9783527607495.

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