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Osaterone acetate

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Osaterone acetate
Clinical data
Trade namesYpozane
Other namesTZP-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, Osaterone acetate (JAN JP)
Routes of
administration
By mouth (tablets)
Drug classSteroidal antiandrogen; Progestogen; Progestin; Progestogen ester
ATCvet code
Legal status
Legal status
Pharmacokinetic data
Protein bindingOsaterone acetate: 90%
15β-Hydroxyosaterone acetate: 80%[3]
(Both mainly to albumin)[3]
MetabolismLiver[3]
Metabolites15β-Hydroxyosaterone acetate[3]
Elimination half-lifeDogs: 80 hours to 197 ± 109 hours[3][4]
ExcretionBile: 60%[3]
Urine: 25%[3]
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.215.750 Edit this at Wikidata
Chemical and physical data
FormulaC22H27ClO5
Molar mass406.90 g·mol−1
3D model (JSmol)
  • CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)OCC34C)Cl)C)OC(=O)C
  • InChI=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
  • Key:KKTIOMQDFOYCEN-OFUYBIASSA-N

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.[3][5][6] It is given by mouth.[3]

Osaterone acetate is an antiandrogen, and hence is an antagonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone.[3] 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.[3]

Osaterone acetate was introduced for veterinary use in 2007.[1][3][7][8]

Uses

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Veterinary

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Osaterone acetate is used in veterinary medicine for the treatment of benign prostatic hyperplasia (BPH) in dogs.[3][5][6] 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,[9] and can be used long-term.[6]

Available forms

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Osaterone acetate comes in the form of 1.875 mg, 3.75 mg, 7.5 mg, and 15 mg oral tablets for veterinary use.[3]

Side effects

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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.[10] It can also decrease cortisol levels, interfere with adrenocorticotropic hormone response, induce or exacerbate adrenal insufficiency, and exacerbate diabetes mellitus.[11][10]

Pharmacology

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Pharmacodynamics

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Osaterone acetate is a steroidal antiandrogen, progestin, and antigonadotropin.[3] It has virtually no estrogenic or androgenic activity.[5] Its side-effect profile indicates that it possesses clinically relevant glucocorticoid activity.[11][10] An active metabolite of osaterone acetate, 15β-hydroxyosaterone acetate, has potent antiandrogenic activity similarly to osaterone acetate.[3] Osaterone acetate treats BPH in dogs by reducing the actions of androgens in the prostate gland.[3]

Pharmacokinetics

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The major active metabolite of osaterone acetate is 15β-hydroxyosaterone acetate.[3] Osaterone acetate has a long biological half-life of 80 hours to 197 ± 109 hours in dogs.[3][4]

Chemistry

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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.[8] It is a derivative of the less potent chlormadinone acetate.[5] The medication is the C17α acetate ester of osaterone.[8]

History

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Osaterone acetate was approved for veterinary use in the European Union under the brand name Ypozane in 2007.[1][3][7][8]

Society and culture

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Generic names

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Osaterone acetate is the generic name of the drug.[1][8] Osaterone is the INNTooltip International Nonproprietary Name of the deacetylated parent compound.[8]

Brand names

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Osaterone acetate is marketed under the brand name Ypozane by Virbac throughout the European Union.[1][8]

Research

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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.[5][12]

References

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  1. ^ a b c d e "Ypozane EPAR". European Medicines Agency. 18 January 2007. Retrieved 28 June 2024.
  2. ^ "Ypozane PI". Union Register of veterinary medicinal products. 15 January 2007. Retrieved 29 June 2024.
  3. ^ a b c d e f g h i j k l m n o p q r s t "Ypozane for Dogs" (PDF). European Medicines Agency. Archived from the original (PDF) on 20 June 2018. Retrieved 20 February 2018.
  4. ^ a b Maddison JE, Page SW, Church D (2008). Small Animal Clinical Pharmacology. Elsevier Health Sciences. pp. 536–. ISBN 978-0-7020-2858-8.
  5. ^ a b c d e Weber GF (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 316–. ISBN 978-3-319-13278-5.
  6. ^ a b c Greer ML (18 December 2014). Canine Reproduction and Neonatology. Teton NewMedia. pp. 296–. ISBN 978-1-4987-2850-8.
  7. ^ a b Emmerich IU, Ungemach FR (2008). "Neue Arzneimittel für Kleintiere 2007". Tierärztliche Praxis Ausgabe K: Kleintiere/Heimtiere. 36 (5): 311–22. doi:10.1055/s-0038-1622691. S2CID 257184365.
  8. ^ a b c d e f g "Osaterone". Drugs.com.
  9. ^ Cote E (9 December 2014). Clinical Veterinary Advisor: Dogs and Cats. Elsevier Health Sciences. pp. 848–. ISBN 978-0-323-24074-1.
  10. ^ a b c Lamm C, Makloski C (28 May 2012). Theriogenology, An Issue of Veterinary Clinics: Small Animal Practice. Elsevier Health Sciences. pp. 112–. ISBN 978-1-4557-4447-3.
  11. ^ a b Ettinger SJ, Feldman EC (24 December 2009). Textbook of Veterinary Internal Medicine. Elsevier Health Sciences. pp. 2055–. ISBN 978-1-4377-0282-8.
  12. ^ Schröder FH, Radlmaier A (2009). "Steroidal Antiandrogens". In Jordan VC, Furr BJ (eds.). Hormone Therapy in Breast and Prostate Cancer. Cancer Drug Discovery and Development. Humana Press. pp. 325–346. doi:10.1007/978-1-59259-152-7_15. ISBN 978-1-60761-471-5.

Further reading

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