osaterone acetate
{{Short description|Chemical compound}}
{{Use dmy dates|date=June 2024}}
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{{Infobox drug
| image = Osaterone acetate.svg
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| INN = Osaterone
| pronounce =
| tradename = Ypozane
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| pregnancy_AU =
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| routes_of_administration = By mouth (tablets)
| class = Steroidal antiandrogen; Progestogen; Progestin; Progestogen ester
| ATCvet =
| ATC_prefix = None
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| legal_EU = Rx-only
| legal_EU_comment = {{cite web | title=Ypozane EPAR | website=European Medicines Agency | date=18 January 2007 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/ypozane | access-date=28 June 2024}}{{cite web | title=Ypozane PI | website=Union Register of veterinary medicinal products | date=15 January 2007 | url=https://ec.europa.eu/health/documents/community-register/html/v068.htm | access-date=29 June 2024}}
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| bioavailability =
| protein_bound = Osaterone acetate: 90%
15β-Hydroxyosaterone acetate: 80%
(Both mainly to albumin)
| metabolism = Liver
| metabolites = 15β-Hydroxyosaterone acetate
| onset =
| elimination_half-life = Dogs: 80 hours to 197 ± 109 hours
| duration_of_action =
| excretion = Bile: 60%
Urine: 25%
| CAS_number = 105149-00-6
| CAS_supplemental =
| PubChem = 114992
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 102924
| UNII = FR26FSV5EZ
| KEGG = D11105
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| synonyms = TZP-4238; Gestoxarone acetate; 2-Oxachloromadinone acetate; 17α-Acetoxy-6-chloro-2-oxa-6-dehydroprogesterone; 17α-Acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione
| IUPAC_name = [(1R,3aS,3bR,9aR,9bS,11aS)-1-acetyl-5-chloro-9a,11a-dimethyl-7-oxo-2,3,3a,3b,9,9b,10,11-octahydroindeno[4,5-h]isochromen-1-yl] acetate
| C=22 | H=27 | Cl=1 | O=5
| SMILES = CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)OCC34C)Cl)C)OC(=O)C
| StdInChI = 1S/C22H27ClO5/c1-12(24)22(28-13(2)25)8-6-16-14-9-18(23)17-10-19(26)27-11-20(17,3)15(14)5-7-21(16,22)4/h9-10,14-16H,5-8,11H2,1-4H3/t14-,15+,16+,20-,21+,22+/m1/s1
| StdInChI_comment =
| StdInChIKey = KKTIOMQDFOYCEN-OFUYBIASSA-N
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Osaterone acetate, sold under the brand name Ypozane, is a medication which is used in veterinary medicine for the treatment of enlarged prostate in dogs.{{cite web | title = Ypozane for Dogs | work = European Medicines Agency | url = http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000112/WC500069537.pdf | access-date = 20 February 2018 | archive-date = 20 June 2018 | archive-url = https://web.archive.org/web/20180620004709/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000112/WC500069537.pdf | url-status = dead }}{{cite book| vauthors = Weber GF |title=Molecular Therapies of Cancer|url=https://books.google.com/books?id=dhs_CgAAQBAJ&pg=PA316|date=22 July 2015|publisher=Springer|isbn=978-3-319-13278-5|pages=316–}}{{cite book| vauthors = Greer ML |title=Canine Reproduction and Neonatology|url=https://books.google.com/books?id=GlFsBgAAQBAJ&pg=PA296|date=18 December 2014|publisher=Teton NewMedia|isbn=978-1-4987-2850-8|pages=296–}} It is given by mouth.
Osaterone acetate is an antiandrogen, and hence is an antagonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone. It is also a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.
Osaterone acetate was introduced for veterinary use in 2007.
Uses
=Veterinary=
Osaterone acetate is used in veterinary medicine for the treatment of benign prostatic hyperplasia (BPH) in dogs. It has been found to produce remission of clinical symptoms of BPH in 83% of dogs for six months after a single one-week course of treatment,{{cite book| vauthors = Cote E |title=Clinical Veterinary Advisor: Dogs and Cats|url=https://books.google.com/books?id=NmziBQAAQBAJ&pg=PA848|date=9 December 2014|publisher=Elsevier Health Sciences|isbn=978-0-323-24074-1|pages=848–}} and can be used long-term.
=Available forms=
Side effects
Side effects of osaterone acetate include diminished sperm quality (for up to 6 weeks post-treatment), transient elevation of liver enzymes (caution should be observed with known liver disease), vomiting, diarrhea, polyuria/polydipsia, lethargy, and hyperplasia of the mammary glands. It can also decrease cortisol levels, interfere with adrenocorticotropic hormone response, induce or exacerbate adrenal insufficiency, and exacerbate diabetes mellitus.{{cite book| vauthors = Ettinger SJ, Feldman EC |title=Textbook of Veterinary Internal Medicine|url=https://books.google.com/books?id=4Qzau1jagOYC&pg=PA2055|date=24 December 2009|publisher=Elsevier Health Sciences|isbn=978-1-4377-0282-8|pages=2055–}}{{cite book | vauthors = Lamm C, Makloski C |title=Theriogenology, An Issue of Veterinary Clinics: Small Animal Practice|url=https://books.google.com/books?id=gtoRaSR2NxcC&pg=PT112|date=28 May 2012|publisher=Elsevier Health Sciences|isbn=978-1-4557-4447-3|pages=112–}}
Pharmacology
=Pharmacodynamics=
Osaterone acetate is a steroidal antiandrogen, progestin, and antigonadotropin. It has virtually no estrogenic or androgenic activity. Its side-effect profile indicates that it possesses clinically relevant glucocorticoid activity. An active metabolite of osaterone acetate, 15β-hydroxyosaterone acetate, has potent antiandrogenic activity similarly to osaterone acetate. Osaterone acetate treats BPH in dogs by reducing the actions of androgens in the prostate gland.
=Pharmacokinetics=
The major active metabolite of osaterone acetate is 15β-hydroxyosaterone acetate. Osaterone acetate has a long biological half-life of 80 hours to 197 ± 109 hours in dogs.{{cite book| vauthors = Maddison JE, Page SW, Church D |title=Small Animal Clinical Pharmacology|url=https://books.google.com/books?id=RpsROVqemk8C&pg=PA536|year=2008|publisher=Elsevier Health Sciences|isbn=978-0-7020-2858-8|pages=536–}}
Chemistry
{{See also|Steroidal antiandrogen|List of steroidal antiandrogens|List of progestogens|Progestogen ester|List of progestogen esters}}
Osaterone acetate, also known as 2-oxachloromadinone acetate, as well as 17α-acetoxy-6-chloro-2-oxa-6-dehydroprogesterone or 17α-acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone. It is a derivative of the less potent chlormadinone acetate. The medication is the C17α acetate ester of osaterone.
History
Osaterone acetate was approved for veterinary use in the European Union under the brand name Ypozane in 2007.{{cite journal | vauthors = Emmerich IU, Ungemach FR | title = Neue Arzneimittel für Kleintiere 2007 | journal = Tierärztliche Praxis Ausgabe K: Kleintiere/Heimtiere. | date = 2008 | volume = 36 | issue = 5 | pages = 311–22 | doi = 10.1055/s-0038-1622691 | s2cid = 257184365 }}
Society and culture
=Generic names=
Osaterone acetate is the generic name of the drug.{{cite web | title = Osaterone | url = https://www.drugs.com/international/osaterone.html | work = Drugs.com }} Osaterone is the {{abbrlink|INN|International Nonproprietary Name}} of the deacetylated parent compound.
=Brand names=
Research
Osaterone acetate was also investigated in Japan in the treatment of prostate cancer and BPH in humans but was ultimately never marketed for such purposes.{{cite book | vauthors = Schröder FH, Radlmaier A | chapter = Steroidal Antiandrogens | pages = 325–346 | doi = 10.1007/978-1-59259-152-7_15 | title = Hormone Therapy in Breast and Prostate Cancer | series = Cancer Drug Discovery and Development | veditors = Jordan VC, Furr BJ | year = 2009 | publisher = Humana Press | isbn = 978-1-60761-471-5}}
References
{{Reflist}}
Further reading
{{refbegin}}
- {{cite book | vauthors = Schröder FH, Radlmaier A |title=Hormone Therapy in Breast and Prostate Cancer|chapter=Steroidal Antiandrogens|series=Cancer Drug Discovery and Development |year=2009|pages=325–346|publisher=Humana Press |doi=10.1007/978-1-59259-152-7_15|isbn=978-1-60761-471-5}}
{{refend}}
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{{Drugs used in benign prostatic hypertrophy}}
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{{Navboxes
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{{Androgen receptor modulators}}
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