Editing Progesterone (section)

{{Short description|Sex hormone}}
{{Use dmy dates|date=December 2023}}
{{About|progesterone as a hormone|its use as a medication|progesterone (medication)}}
{{cs1 config|name-list-style=vanc}}
{{Chembox
<!-- Images -->| Name           =
| ImageFile1     = Progesterone.svg
| ImageClass1    = skin-invert
| ImageSize1     = 225px
| ImageAlt1      = The chemical structure of progesterone.
| ImageFile2     = Progesterone-3D-balls.png
| ImageSize2     = 225px
| ImageAlt2      = A ball-and-stick model of progesterone.
<!-- Names -->| IUPACName      = Pregn-4-ene-3,20-dione<ref name="Adler-2012">{{cite book | vauthors = Adler N, Pfaff D, Goy RW | title = Handbook of Behavioral Neurobiology Volume 7 Reproduction | date = 6 December 2012 | publisher = Plenum Press | location = New York | isbn = 978-1-4684-4834-4 | page = 189 | edition = 1st | url = https://books.google.com/books?id=MoDrBwAAQBAJ&q=pregn-4-ene-3,20-dione;+abbreviated+as+P4&pg=PA189 | access-date = 4 July 2015 | archive-date = 14 January 2023 | archive-url = https://web.archive.org/web/20230114024946/https://books.google.com/books?id=MoDrBwAAQBAJ&q=pregn-4-ene-3,20-dione;+abbreviated+as+P4&pg=PA189 | url-status = live }}</ref><ref name="ChEBI-17026">{{cite web|title=progesterone (CHEBI:17026)|url=http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=309FCC7D184C0AD58410071F3F163155?chebiId=17026&structureView=applet&viewTermLineage=|website=ChEBI|publisher=European Molecular Biology Laboratory-EBI|access-date=4 July 2015|archive-date=20 March 2016|archive-url=https://web.archive.org/web/20160320211423/http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=309FCC7D184C0AD58410071F3F163155?chebiId=17026&structureView=applet&viewTermLineage=|url-status=live}}</ref>
| SystematicName = (1''S'',3a''S'',3b''S'',9a''R'',9b''S'',11a''S'')-1-Acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7''H''-cyclopenta[''a'']phenanthren-7-one
| OtherNames     = P4;<ref name="James2015" /> Pregnenedione
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 444066687
<!-- Sections -->| Section1       = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 57-83-0
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17026
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 103
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5773
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00396
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C00410
| PubChem = 5994
| SMILES = CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RJKFOVLPORLFTN-LEKSSAKUSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4G7DS2Q64Y
  }}
| Section2       = {{Chembox Properties
| C=21 | H=30 | O=2
| MolarMass = 314.469 g/mol
| Appearance =
| Density = 1.171
| MeltingPt = 126
| BoilingPt =
| Solubility =
| LogP = 4.04<ref name="chemsrc">{{cite web|url=https://www.chemsrc.com/en/cas/57-83-0_1068061.html|title=Progesterone_msds|access-date=19 April 2018|archive-date=12 February 2021|archive-url=https://web.archive.org/web/20210212022152/https://www.chemsrc.com/en/cas/57-83-0_1068061.html|url-status=live}}</ref>
  }}
| Section3       = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
| Section4       =
| Section5       =
| Section6       = {{Chembox Pharmacology
| ATCvet =
| ATCCode_prefix = G03
| ATCCode_suffix = DA04
| ATC_Supplemental =
| AdminRoutes = [[Oral administration|By mouth]], [[topical medication|topical]]/[[transdermal]], [[intravaginal administration|vaginal]], [[intramuscular injection]], [[subcutaneous injection]], [[implant (medicine)|subcutaneous implant]]
| Bioavail = {{abbr|OMP|oral micronized progesterone}}: <10%<ref name="pmid12215716" /><ref name="pmid8513955" />
| Excretion = [[Renal]]
| HalfLife = {{abbr|OMP|oral micronized progesterone}}: 16–18 hours<ref name="pmid12215716" /><ref name="pmid8513955" /><ref name="Zutshi-2005">{{cite book | vauthors = Zutshi V, Rathore AM, Sharma K | title = Hormones in Obstetrics and Gynaecology | url = https://books.google.com/books?id=IBxBbaDjXw0C&pg=PA74 | date = 1 January 2005 | publisher = Jaypee Brothers Publishers | isbn = 978-81-8061-427-9 | page = 74 }}{{Dead link|date=February 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><br />{{abbr|IM|Intramuscular}}: 22–26 hours<ref name="pmid8513955" /><ref name="pmid26342177">{{cite journal | vauthors = Cometti B | title = Pharmaceutical and clinical development of a novel progesterone formulation | journal = Acta Obstetricia et Gynecologica Scandinavica | volume = 94 | issue = Suppl 161 | pages = 28–37 | date = November 2015 | pmid = 26342177 | doi = 10.1111/aogs.12765 | s2cid = 31974637 | doi-access = free }}</ref><br />{{abbr|SC|Subcutaneous}}: 13–18 hours<ref name="pmid26342177" />
| Metabolism = [[Hepatic]] ([[CYP2C19]], [[CYP3A4]], [[CYP2C9]], [[5α-reductase]], {{abbrlink|3α-HSD|3α-hydroxysteroid dehydrogenase}}, [[17α-hydroxylase]], [[21-hydroxylase]], {{abbrlink|20α-HSD|20α-hydroxysteroid dehydrogenase}})<ref name="pmid9328296">{{cite journal | vauthors = Yamazaki H, Shimada T | title = Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes | journal = Archives of Biochemistry and Biophysics | volume = 346 | issue = 1 | pages = 161–169 | date = October 1997 | pmid = 9328296 | doi = 10.1006/abbi.1997.0302 }}</ref><ref name="McKayWalters2013">{{cite book | vauthors = McKay GA, Walters MR | title = Lecture Notes: Clinical Pharmacology and Therapeutics | url = https://books.google.com/books?id=OGOqcfN_Cc8C&pg=PT33 | date = 6 February 2013 | publisher = John Wiley & Sons | isbn = 978-1-118-34489-7 | page = 33 | access-date = 27 June 2015 | archive-date = 14 January 2023 | archive-url = https://web.archive.org/web/20230114024939/https://books.google.com/books?id=OGOqcfN_Cc8C&pg=PT33 | url-status = live }}</ref>
| ProteinBound = • [[Human serum albumin|Albumin]]: 80%<br />• [[Corticosteroid-binding globulin|CBG]]: 18%<br />• [[Sex hormone-binding globulin|SHBG]]: <1%<br />• Free: 1–2%<ref name="FritzSperoff2012">{{cite book | vauthors = Fritz MA, Speroff L  | title = Clinical Gynecologic Endocrinology and Infertility | url = https://books.google.com/books?id=KZLubBxJEwEC&pg=PA44 | date = 28 March 2012 | publisher = Lippincott Williams & Wilkins | isbn = 978-1-4511-4847-3 | pages = 44– }}</ref><ref name="MarshallD.2008">{{cite book | vauthors = Marshall WJ, Bangert SK | title = Clinical Chemistry | url = https://books.google.com/books?id=Gjc704GR5YEC&pg=PA192 | year = 2008 | publisher = Elsevier Health Sciences | isbn = 978-0-7234-3455-9 | pages = 192– | access-date = 5 October 2016 | archive-date = 14 January 2023 | archive-url = https://web.archive.org/web/20230114024953/https://books.google.com/books?id=Gjc704GR5YEC&pg=PA192 | url-status = live }}</ref>
  }}
}}

'''Progesterone''' ({{IPAc-en|p|r|oʊ|ˈ|dʒ|ɛ|s|t|ər|oʊ|n|audio=LL-Q1860 (eng)-Flame, not lame-progesterone.wav}}; '''P4''') is an [[endogenous]] [[steroid]] and [[progestogen]] [[sex hormone]] involved in the [[menstrual cycle]], [[pregnancy]], and [[embryogenesis]] of humans and other species.<ref name="James2015" /><ref name="KingBrucker2010" /> It belongs to a group of steroid hormones called the [[progestogen]]s<ref name="KingBrucker2010" /> 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 [[steroid]]s, including the [[sex hormone]]s and the [[corticosteroid]]s, and plays an important role in brain function as a [[neurosteroid]].<ref name="pmid11108866">{{cite journal | vauthors = Baulieu E, Schumacher M | title = Progesterone as a neuroactive neurosteroid, with special reference to the effect of progesterone on myelination | journal = Steroids | volume = 65 | issue = 10–11 | pages = 605–612 | year = 2000 | pmid = 11108866 | doi = 10.1016/s0039-128x(00)00173-2 | s2cid = 14952168 }}</ref>

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 cancer|uterine]] or [[cervical cancer]], in [[hormone replacement therapy]], and in [[feminizing hormone therapy]].<ref name="pmid30608551">{{cite journal | vauthors = Prior JC | title = Progesterone Is Important for Transgender Women's Therapy-Applying Evidence for the Benefits of Progesterone in Ciswomen | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 104 | issue = 4 | pages = 1181–1186 | date = April 2019 | pmid = 30608551 | doi = 10.1210/jc.2018-01777 | quote = 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 | s2cid = 58620122 | doi-access = free }}</ref> It was first prescribed in 1934.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=47X |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA47X }}</ref>
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