Osaterone acetate

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Osaterone acetate
Osaterone acetate.svg
Clinical data
Trade names Ypozane
Synonyms TZP-4238; 2-Oxachloromadinone acetate; 17α-Acetoxy-6-chloro-2-oxa-6-dehydroprogesterone; 17α-Acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione
Routes of
administration
By mouth (tablets)
Drug class Steroidal antiandrogen; Progestin; Progestogen; Progestogen ester
Pharmacokinetic data
Protein binding Osaterone acetate: 90%
15β-Hydroxyosaterone acetate: 80%[1]
(Both mainly to albumin)[1]
Metabolism Liver[1]
Metabolites 15β-Hydroxyosaterone acetate[1]
Elimination half-life Dogs: 80 hours to 197 ± 109 hours[1][2]
Excretion Bile: 60%[1]
Urine: 25%[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C22H27ClO5
Molar mass 406.900 g/mol
3D model (JSmol)

Osaterone acetate, sold under the brand name Ypozane, is a medication which is used in veterinary medicine in Europe in the treatment of enlarged prostate in dogs.[1][3][4] It is given by mouth.[1]

Osaterone acetate is an antiandrogen, and hence is an antagonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone.[1] 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.[1]

Osaterone acetate was introduced for veterinary use in 2007.[5] It is marketed in Europe.[6][1]

Uses[edit]

Veterinary[edit]

Osaterone acetate is used in veterinary medicine in Europe in the treatment of benign prostatic hyperplasia (BPH) in dogs.[1][3][4] 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,[7] and can be used long-term.[4]

Available forms[edit]

Osaterone acetate comes in the form of 1.875 mg, 3.75 mg, 7.5 mg, and 15 mg oral tablets for veterinary use.[1]

Side effects[edit]

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.[8] It can also decrease cortisol levels, interfere with adrenocorticotropic hormone response, induce or exacerbate adrenal insufficiency, and exacerbate diabetes mellitus.[9][8]

Pharmacology[edit]

Pharmacodynamics[edit]

Osaterone acetate is a steroidal antiandrogen, progestin, and antigonadotropin.[1] It has virtually no estrogenic or androgenic activity.[3] Its side-effect profile indicates that it possesses clinically relevant glucocorticoid activity.[9][8] An active metabolite of osaterone acetate, 15β-hydroxyosaterone acetate, has potent antiandrogenic activity similarly to osaterone acetate.[1] Osaterone acetate treats BPH in dogs by reducing the actions of androgens in the prostate gland.[1]

Pharmacokinetics[edit]

The major active metabolite of osaterone acetate is 15β-hydroxyosaterone acetate.[1] Osaterone acetate has a long biological half-life of 80 hours to 197 ± 109 hours in dogs.[1][2]

Chemistry[edit]

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.[6] It is a derivative of the less potent chlormadinone acetate.[3] The medication is the C17α acetate ester of osaterone.[6]

History[edit]

Osaterone acetate was introduced for veterinary use in Europe under the brand name Ypozane in 2007.[6][5][1]

Society and culture[edit]

Generic names[edit]

Osaterone acetate is the generic name of the drug.[6] Osaterone is the INN of the deacetylated parent compound.[6]

Brand names[edit]

Osaterone acetate is marketed under the brand name Ypozane by Virbac.[6]

Availability[edit]

Osaterone acetate is available widely throughout Europe, including in Belgium, Finland, France, Germany, Italy, the Netherlands, Norway, Poland, Sweden, Switzerland, and the United Kingdom.[6]

Research[edit]

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.[3][10]

References[edit]

  1. ^ a b c d e f g h i j k l m n o p q r s t http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/veterinary/000112/WC500069537.pdf
  2. ^ a b Jill E. Maddison; Stephen W. Page; David Church (BVSc.) (2008). Small Animal Clinical Pharmacology. Elsevier Health Sciences. pp. 536–. ISBN 0-7020-2858-4. 
  3. ^ a b c d e Georg F. Weber (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 316–. ISBN 978-3-319-13278-5. 
  4. ^ a b c Marthina L. Greer (18 December 2014). Canine Reproduction and Neonatology. Teton NewMedia. pp. 296–. ISBN 978-1-4987-2850-8. 
  5. ^ a b Emmerich, I. U., & Ungemach, F. R. (2008). Neue Arzneimittel für Kleintiere 2007. Tierärztliche Praxis K: Kleintiere/Heimtiere, 36(05), 311-322. 10.1055/s-0038-1622691 https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0038-1622691
  6. ^ a b c d e f g h https://www.drugs.com/international/osaterone.html
  7. ^ Etienne Cote (9 December 2014). Clinical Veterinary Advisor: Dogs and Cats. Elsevier Health Sciences. pp. 848–. ISBN 978-0-323-24074-1. 
  8. ^ a b c Catherine Lamm; Chelsea Makloski (28 May 2012). Theriogenology, An Issue of Veterinary Clinics: Small Animal Practice. Elsevier Health Sciences. pp. 112–. ISBN 1-4557-4447-6. 
  9. ^ a b Stephen J. Ettinger; Edward C. Feldman (24 December 2009). Textbook of Veterinary Internal Medicine. Elsevier Health Sciences. pp. 2055–. ISBN 1-4377-0282-1. 
  10. ^ JORDAN V. CRAIG; B.J.A. Furr (5 February 2010). Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. pp. 328–. ISBN 978-1-59259-152-7. 

External links[edit]