Osaterone acetate Trade names Ypozane Other names 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 Routes of administration By mouth (tablets )Drug class Steroidal antiandrogen ; Progestogen ; Progestin ; Progestogen ester 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]
[(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 ECHA InfoCard 100.215.750 Formula C 22 H 27 Cl O 5 Molar mass 406.90 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 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 [ ]
Further reading [ ]
Schröder FH, Radlmaier A (2009). "Steroidal Antiandrogens". Hormone Therapy in Breast and Prostate Cancer . pp. 325–346. doi :10.1007/978-1-59259-152-7_15 . ISBN 978-1-60761-471-5 .
External links [ ]
Medical uses
Drugs used in benign prostatic hyperplasia (G04C )
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# WHO-EM
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# WHO-EM
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Antagonists Others
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Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
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List of corticosteroids