{{Short description|Chemical compound}} {{About|a progestin compound|the pharmaceutical drug|megestrol acetate}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{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 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VXIMPSPISRVBPZ-NWUMPJBXSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_category = | legal_status = | routes_of_administration = }}
'''Megestrol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}) is a progestin of the 17α-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, endometrial cancer, and 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 derivative megestrol acetate is also a progestogen, which, in contrast to megestrol itself, has been extensively used as a pharmaceutical 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 patients, and as a palliative treatment of endometrial and breast cancers. 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 * Medroxyprogesterone acetate
== References == {{Reflist}}
{{Progesterone receptor modulators}}
Category:Tertiary alcohols Category:Conjugated dienes Category:Diketones Category:Pregnanes Category:Progestogens Category:Enones