Testosterone phenylacetate

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 (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was one of the first testosterone esters to be introduced.[4] However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.[4]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. ↑ 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. 1 2 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. 1 2 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. 1 2 3 Federal Register. Office of the Federal Register, National Archives and Records Service, General Services Administration. September 1977. pp. 52488–.
  9. 1 2 3 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. 1 2 3 4 5 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.



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