Proligestone
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 14α,17α-(propylidenebis(oxy))pregn-4-ene-3,20-dione
| image = Proligestone.svg
| width = 225px
| tradename = Covinan, Delvosteron
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| class = Progestogen; Progestin
| bioavailability =
| protein_bound =
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| CAS_number = 23873-85-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 55772LJ01V
| ATC_prefix = G03
| ATC_suffix = DA90
| PubChem = 71906
| DrugBank =
| ChemSpiderID = 64917
| ChEMBL = 2106696
| KEGG = D08429
| synonyms = 14α,17α-Propylidenedioxyprogesterone; 14α,17α-Dihydroxyprogesterone cyclic acetal with propionaldehyde; 14α,17α-Dihydroxypregn-4-ene-3,20-dione cyclic acetal with propionaldehyde
| C=24 | H=34 | O=4
| SMILES = CCC1O[C@@]23CC[C@]([C@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C)(O1)C(=O)C
| StdInChI = 1S/C24H34O4/c1-5-20-27-23(15(2)25)12-13-24(28-20)19-7-6-16-14-17(26)8-10-21(16,3)18(19)9-11-22(23,24)4/h14,18-20H,5-13H2,1-4H3/t18-,19+,20?,21-,22+,23-,24+/m0/s1
| StdInChIKey = MQSDUYIXZDSLSZ-QSDCUGRSSA-N
}}
Proligestone, sold under the brand names Covinan and Delvosteron, is a progestin medication which is used in veterinary medicine.{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1025|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1025–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA882|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=882–}}{{Cite web |url= https://www.drugs.com/international/proligestone.html |title = List of Progestins | work = Drugs.com }}
Uses
=Veterinary=
Proligestone is used to control estrus in dogs and cats and has also been used to treat hypersexuality in dogs and cats.{{Cite journal|url=https://eurekamag.com/research/000/908/000908843.php|title = Indications for proligestone (Delvosteron) in dogs and cats|journal = Praktische Tierarzt|date = 22 April 1981|volume = 62|issue = 12| vauthors = Mundt S }}
Pharmacology
=Pharmacodynamics=
Proligestone is a progestogen, or an agonist of the progesterone receptor (PR).
Chemistry
{{See also|List of progestogens|List of progestogen esters#Cyclic ketals of progesterone derivatives}}
Proligestone, also known as 14α,17α-propylidenedioxyprogesterone or as 14α,17α-dihydroxyprogesterone cyclic acetal with propionaldehyde, as well as 14α,17α-propylidenedioxypregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone. It is a C14α,17α cyclic ketal of 14α,17α-dihydroxyprogesterone.{{cite book| vauthors = Marler EE |title=Pharmacological and Chemical Synonyms: A Collection of Names of Drugs, Pesticides and Other Compounds Drawn from the Medical Literature of the World|url=https://books.google.com/books?id=SA-0AAAAIAAJ|year=1976|publisher=Excerpta Medica|isbn=978-90-219-0298-2|page=376}}{{cite book| vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=1XBqAAAAMAAJ|date=4 October 2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=2569}}{{cite web | title = Proligestone | work = Medical Subject Headings: Supplementary chemical records | publisher = U.S. National Library of Medicine |url=https://www.ncbi.nlm.nih.gov/mesh/?term=Proligestone}}
History
Proligestone was described as early as 1968 and was introduced for veterinary use in 1975.{{cite book|title=Official Gazette of the United States Patent and Trademark Office: Trademarks|url=https://books.google.com/books?id=-fnQAAAAMAAJ|year=1984|publisher=U.S. Department of Commerce, Patent and Trademark Office|page=30}}{{cite journal | vauthors = Vanos JL, Oldenkamp EP | title = Oestrus control in bitches with proligestone, a new progestational steroid | journal = The Journal of Small Animal Practice | volume = 19 | issue = 9 | pages = 521–529 | date = September 1978 | pmid = 567718 | doi = 10.1111/j.1748-5827.1978.tb05534.x }}
Society and culture
=Generic names=
Proligestone is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}.
=Brand names=
=Availability=
Proligestone is or has been available for veterinary use in Argentina, Australia, Austria, Belgium, Czechoslovakia, France, Germany, Ireland, Italy, the Netherlands, New Zealand, Poland, South Africa, Switzerland, and the United Kingdom.
References
{{Reflist}}
{{Progestogens and antiprogestogens}}
{{Progesterone receptor modulators}}
Category:Cyclic acetals with aldehydes