Testosterone phenylacetate

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was one of the first testosterone esters to be introduced.[4] However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.[4]

Not to be confused with Testosterone phenylpropionate, Testosterone propionate, or Testosterone isobutyrate.
Testosterone phenylacetate
Clinical data
Trade namesPerandren, Androject
Other namesTPA
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Identifiers
IUPAC name
  • [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 2-phenylacetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H34O3
Molar mass406.557 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CC4=CC=CC=C4)CCC5=CC(=O)CC[C@]35C
InChI
  • InChI=1S/C27H34O3/c1-26-14-12-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)15-13-23(21)26)30-25(29)16-18-6-4-3-5-7-18/h3-7,17,21-24H,8-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1
  • Key:WIJSFCWRMNIREB-ZLQWOROUSA-N

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. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
  3. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  4. Walter Sneader (31 October 2005). Drug Discovery: A History. John Wiley & Sons. pp. 205–. ISBN 978-0-470-01552-0.
  5. Escamilla RF (February 1960). "Newer hormonal preparations". Calif Med. 92: 121–4. PMC 1578009. PMID 13849734.
  6. Milton John Chatton (1973). Current Diagnosis & Treatment. Lange Medical Publications. ISBN 9780870411236. 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.
  8. Federal Register. Office of the Federal Register, National Archives and Records Service, General Services Administration. September 1977. pp. 52488–.
  9. John Christian Krantz; Charles Jelleff Carr; Domingo M. Aviado (1972). 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. p. 670. ISBN 9780683002928.
  10. Hans Lisser; Roberto F. Escamilla (1962). Atlas of Clinical Endocrinology. Mosby. Testosterone phenylacetate (Perandren phenylacetate)—Long-acting suspension of macrocrystals. Dose, 100 to 200 mg. intramuscularly every 2 to 4 weeks.
  11. Reifenstein EC, Howard P, Turner HH, Lowrimore BS (May 1954). "Studies comparing the effects of certain testosterone esters in man". J Am Geriatr Soc. 2 (5): 293–8. doi:10.1111/j.1532-5415.1954.tb00207.x. PMID 13162731. S2CID 39965563.
  12. Modern Drugs: The Journal of the Modern Drug Encyclopedia. Drug Publications. 1955.



This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.