testosterone phenylacetate

{{Short description|Chemical compound}}

{{Distinguish|Testosterone phenylpropionate|Testosterone propionate|Testosterone isobutyrate}}

{{Drugbox

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| 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

| image = Testosterone phenylacetate.svg

| image_class = skin-invert-image

| width = 250px

| tradename = Perandren, Androject

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| routes_of_administration = Intramuscular injection

| class = Androgen; Anabolic steroid; Androgen ester

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| CAS_number_Ref =

| CAS_number = 5704-03-0

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| PubChem = 9931194

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| ChemSpiderID_Ref =

| ChemSpiderID = 8106825

| UNII = WAD1QAK81D

| ChEMBL = 1697796

| KEGG = D06086

| synonyms = TPA

| C=27 | H=34 | O=3

| 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

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = WIJSFCWRMNIREB-ZLQWOROUSA-N

}}

Testosterone phenylacetate (TPA; brand names Perandren, Androject) is an androgen and anabolic steroid and a testosterone ester.{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–642}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA976|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}} 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.{{cite book| vauthors = Sneader W | chapter = Hormone Analogs |title=Drug Discovery: A History| chapter-url = https://books.google.com/books?id=jglFsz5EJR8C&pg=PA205 |date=31 October 2005|publisher=John Wiley & Sons|isbn=978-0-470-01552-0|pages=205–}} However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.

Testosterone phenylacetate was a 50 mg/mL microcrystalline aqueous suspension under the brand name Perandren.{{cite journal | vauthors = Escamilla RF | title = Newer hormonal preparations | journal = California Medicine | volume = 92 | issue = 2 | pages = 121–124 | date = February 1960 | pmid = 13849734 | pmc = 1578009 }}{{cite book| vauthors = Chatton MJ |title=Current Diagnosis & Treatment|url=https://books.google.com/books?id=EsNrAAAAMAAJ|year=1973|publisher=Lange Medical Publications.|isbn=9780870411236|quote=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.}}{{cite book|title=Physicians Desk Reference to Pharmaceutical Specialties and Biologicals|url=https://books.google.com/books?id=o2ojAQAAIAAJ|year=1968|publisher=Medical Economics.|page=624}}{{cite book|title=Federal Register|url=https://books.google.com/books?id=jpBjXBCWw74C&pg=PA52488|date=September 1977|publisher=Office of the Federal Register, National Archives and Records Service, General Services Administration|pages=52488–}}{{cite book| vauthors = Krantz JC, Carr CJ, Aviado DM |title=Krantz and Carr's Pharmacologic principles of medical practice: a textbook on pharmacology and therapeutics for students and practitioners of medicine, pharmacy, and dentistry|url=https://books.google.com/books?id=C-tsAAAAMAAJ|year=1972|publisher=Williams & Wilkins|page=670|isbn=9780683002928}} It was used at a dosage of 50 to 200 mg by intramuscular injection once every 2 to 5 weeks.{{cite book | vauthors = Lisser H, Escamilla RF |title=Atlas of Clinical Endocrinology|url=https://books.google.com/books?id=ck5sAAAAMAAJ|year=1962|publisher=Mosby|quote=Testosterone phenylacetate (Perandren phenylacetate)—Long-acting suspension of macrocrystals. Dose, 100 to 200 mg. intramuscularly every 2 to 4 weeks.}} The medication was used to treat hypogonadism and eunuchoidism in males and for palliation of breast cancer in females. It was developed by Ciba Pharmaceutical Company.

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.{{cite journal | vauthors = Reifenstein EC, Howard P, Turner HH, Lowrimore BS | title = Studies comparing the effects of certain testosterone esters in man | journal = Journal of the American Geriatrics Society | volume = 2 | issue = 5 | pages = 293–298 | date = May 1954 | pmid = 13162731 | doi = 10.1111/j.1532-5415.1954.tb00207.x | s2cid = 39965563 }}{{cite book| vauthors = Krantz JC, Carr CJ, Aviado DM |title=Krantz and Carr's Pharmacologic principles of medical practice: a textbook on pharmacology and therapeutics for students and practitioners of medicine, pharmacy, and dentistry|url=https://books.google.com/books?id=C-tsAAAAMAAJ|year=1972|publisher=Williams & Wilkins|page=670|isbn=9780683002928}} In 1955, testosterone phenylacetate in aqueous suspension was said to have the longest duration of any clinically used androgen marketed up to that point.{{cite book|title=Modern Drugs: The Journal of the Modern Drug Encyclopedia|url=https://books.google.com/books?id=VfcjAQAAMAAJ|year=1955|publisher=Drug Publications.}}

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. These symptoms last for several days after the injection and then subside. These reactions do not typically occur with oil solutions. The injection site reactions were viewed as less important in the case of testosterone phenylacetate due to its prolonged duration and less frequent administration.