Osaterone acetate
 | |
| Clinical data | |
|---|---|
| Trade names | Ypozane |
| Other names | 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 | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.215.750 |
| Chemical and physical data | |
| Formula | C22H27ClO5 |
| Molar mass | 406.900 g/mol g·mol−1 |
| 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
Veterinary
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
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
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
Pharmacodynamics
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
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
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
Osaterone acetate was introduced for veterinary use in Europe under the brand name Ypozane in 2007.[6][5][1]
Society and culture
Generic names
Osaterone acetate is the generic name of the drug.[6] Osaterone is the INN of the deacetylated parent compound.[6]
Brand names
Osaterone acetate is marketed under the brand name Ypozane by Virbac.[6]
Availability
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
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
- ^ 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
- ^ 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.
- ^ a b c d e Georg F. Weber (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 316–. ISBN 978-3-319-13278-5.
- ^ a b c Marthina L. Greer (18 December 2014). Canine Reproduction and Neonatology. Teton NewMedia. pp. 296–. ISBN 978-1-4987-2850-8.
- ^ 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
- ^ a b c d e f g h https://www.drugs.com/international/osaterone.html
- ^ Etienne Cote (9 December 2014). Clinical Veterinary Advisor: Dogs and Cats. Elsevier Health Sciences. pp. 848–. ISBN 978-0-323-24074-1.
- ^ 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.
- ^ 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.
- ^ 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