Chemistry:Testosterone phenylacetate

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Short description: Chemical compound
Testosterone phenylacetate
Testosterone phenylacetate.svg
Clinical data
Trade namesPerandren, Androject
Other namesTPA
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC27H34O3
Molar mass406.557 g·mol−1
3D model (JSmol)

Testosterone phenylacetate (TPA; brand names Perandren, Androject) is an androgen and anabolic steroid and a testosterone ester.[1][2][3] Analogously to estradiol benzoate having been one of the first estrogen esters to be introduced, testosterone phenylacetate was one of the first testosterone esters to be introduced.[4] However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.[4]

Testosterone phenylacetate was a 50 mg/mL microcrystalline aqueous suspension under the brand name Perandren.[5][6][7][8][9] It was used at a dosage of 50 to 200 mg by intramuscular injection once every 2 to 5 weeks.[6][10] The medication was used to treat hypogonadism and eunuchoidism in males and for palliation of breast cancer in females.[8][9] It was developed by Ciba Pharmaceutical Company.[8]

A study found that, measured by 17-ketosteroid excretion, 300 mg testosterone propionate in oil solution had a duration of 5 days, 300 mg testosterone propionate in aqueous suspension had a duration of 13 days, 353 mg testosterone cypionate in oil solution had a duration of 24 days, and 354 mg testosterone phenylacetate in aqueous suspension had a duration of 66 days.[11][9] In 1955, testosterone phenylacetate in aqueous suspension was said to have the longest duration of any clinically used androgen marketed up to that point.[12]

Testosterone phenylacetate in aqueous suspension by intramuscular injection, similarly to other aqueous suspension formulations, causes local injection site reactions, including local pain, swelling, and tenderness.[11] These symptoms last for several days after the injection and then subside.[11] These reactions do not typically occur with oil solutions.[11] The injection site reactions were viewed as less important in the case of testosterone phenylacetate due to its prolonged duration and less frequent administration.[11]

See also

References

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–642. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641. 
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA976. 
  3. ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270. 
  4. ↑ 4.0 4.1 "Hormone Analogs". Drug Discovery: A History. John Wiley & Sons. 31 October 2005. pp. 205–. ISBN 978-0-470-01552-0. https://books.google.com/books?id=jglFsz5EJR8C&pg=PA205. 
  5. ↑ "Newer hormonal preparations". California Medicine 92 (2): 121–124. February 1960. PMID 13849734. 
  6. ↑ 6.0 6.1 Current Diagnosis & Treatment. Lange Medical Publications.. 1973. ISBN 9780870411236. https://books.google.com/books?id=EsNrAAAAMAAJ. "Testosterone Phenylacetate (Perandren Phenyl- acetate®): This microcrystalline aqueous suspension for intramuscular use has a prolonged action similar to Depo-Testosterone®. It is supplied as 10 ml vials of 50 mg/ml. The average dose is 50-200 mg every 3-5 weeks." 
  7. ↑ Physicians Desk Reference to Pharmaceutical Specialties and Biologicals. Medical Economics.. 1968. p. 624. https://books.google.com/books?id=o2ojAQAAIAAJ. 
  8. ↑ 8.0 8.1 8.2 Federal Register. Office of the Federal Register, National Archives and Records Service, General Services Administration. September 1977. pp. 52488–. https://books.google.com/books?id=jpBjXBCWw74C&pg=PA52488. 
  9. ↑ 9.0 9.1 9.2 Krantz and Carr's Pharmacologic principles of medical practice: a textbook on pharmacology and therapeutics for students and practitioners of medicine, pharmacy, and dentistry. Williams & Wilkins. 1972. p. 670. ISBN 9780683002928. https://books.google.com/books?id=C-tsAAAAMAAJ. 
  10. ↑ Atlas of Clinical Endocrinology. Mosby. 1962. https://books.google.com/books?id=ck5sAAAAMAAJ. "Testosterone phenylacetate (Perandren phenylacetate)—Long-acting suspension of macrocrystals. Dose, 100 to 200 mg. intramuscularly every 2 to 4 weeks." 
  11. ↑ 11.0 11.1 11.2 11.3 11.4 "Studies comparing the effects of certain testosterone esters in man". Journal of the American Geriatrics Society 2 (5): 293–298. May 1954. doi:10.1111/j.1532-5415.1954.tb00207.x. PMID 13162731. 
  12. ↑ Modern Drugs: The Journal of the Modern Drug Encyclopedia. Drug Publications.. 1955. https://books.google.com/books?id=VfcjAQAAMAAJ. 

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