# Megestrol

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> Markdown URL: https://mediated.wiki/source/Megestrol.md
> Source: https://en.wikipedia.org/wiki/Megestrol
> Source revision: 1352645455
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{{Short description|Chemical compound}}
{{About|a progestin compound|the pharmaceutical drug|megestrol acetate}}
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{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462101940
| IUPAC_name = 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione
| image = Megestrol.svg
| image_class = skin-invert-image
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3562-63-8
| CAS_supplemental = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EA6LD1M70M
| ATC_prefix = G03AC05
| ATC_suffix = 
| PubChem = 1909019090
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB19378
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18023
| ChEBI_Ref = {{ebicite|changed|EBI}} 
| ChEBI = 6722
| C=22 | H=30 | O=3
| smiles = O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@@](O)(C(=O)C)CC[C@@H]12)C)[C@@]3(C)CC4)C
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| StdInChI = 1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1
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| StdInChIKey = VXIMPSPISRVBPZ-NWUMPJBXSA-N
| bioavailability = 
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'''Megestrol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}) is a [progestin](/source/progestin) of the [17α-hydroxyprogesterone](/source/17%CE%B1-hydroxyprogesterone) group which was, until recently, never marketed or used clinically.<ref name="Macdonald1997">{{cite book | vauthors = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=A0THacd46ZsC&pg=PA1267 | access-date = 12 May 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 1267}}</ref><ref name="Index Nominum 2000: International Drug Directory">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA641 | access-date = 28 May 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1 | page = 641}}</ref> It is now used for treatments of [disease-related weight loss](/source/Weight_loss), [endometrial cancer](/source/endometrial_cancer), and [breast cancer](/source/breast_cancer).<ref name=":0">{{cite book | vauthors = Manikkuttiyil C, Nguyen H | chapter = Megestrol |date=2024 | title = StatPearls | chapter-url = https://www.ncbi.nlm.nih.gov/books/NBK559205/ |access-date=2024-04-25 |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=32644631 }}</ref> Its [acylated](/source/acylation) derivative [megestrol acetate](/source/megestrol_acetate) is also a [progestogen](/source/progestogen), which, in contrast to megestrol itself, has been extensively used as a [pharmaceutical](/source/pharmaceutical) [drug](/source/drug).<ref name="Macdonald1997" /><ref name="Index Nominum 2000: International Drug Directory" />

==Medical use==
As of June 2023, megestrol is being used to treat significant weight loss in [HIV/AIDS](/source/HIV%2FAIDS) patients, and as a [palliative](/source/Palliative_care) treatment of [endometrial](/source/Endometrial_cancer) and [breast cancers](/source/Breast_cancer). It can be administered in both tablet and oral suspension forms, with dosages ranging from 100 mg/day to 1600 mg/day depending on the condition being treated.<ref name=":0" />

==Synthesis==
Megestrol can be synthesized from 6a-methylprogesterone.<ref>{{Cite journal | vauthors = Ringold HJ, Ruelas JP, Batres E, Djerassi C | title = Steroids. CXVIII.16-Methyl Derivatives of 17α-Hydroxyprogesterone and of Reichstein's Substance "S" | journal = Journal of the American Chemical Society | volume = 81 | issue = 14 | pages = 3712–3716 | year = 1959 | doi = 10.1021/ja01523a055| bibcode = 1959JAChS..81.3712R }}</ref> <ref>{{US patent|2891079}}</ref>
thumb|center|700px|class=skin-invert-image|Megestrol synthesis

== See also ==
* [Medroxyprogesterone](/source/Medroxyprogesterone)
* [Medroxyprogesterone acetate](/source/Medroxyprogesterone_acetate)

== References ==
{{Reflist}}

{{Progesterone receptor modulators}}

Category:Tertiary alcohols
Category:Conjugated dienes
Category:Diketones
Category:Pregnanes
Category:Progestogens
Category:Enones

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Adapted from the Wikipedia article [Megestrol](https://en.wikipedia.org/wiki/Megestrol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Megestrol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.