Testosterone phenylacetate

Not to be confused with Testosterone phenylpropionate, Testosterone propionate, or Testosterone isobutyrate.

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was one of the first testosterone esters to be introduced.^[4] However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.^[4]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

Clinical data
Trade names	Perandren, Androject
Other names	TPA
Routes of administration	Intramuscular injection
Drug class	Androgen; 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	5704-03-0
PubChem CID	9931194
ChemSpider	8106825
UNII	WAD1QAK81D
KEGG	D06086
ChEMBL	ChEMBL1697796
CompTox Dashboard (EPA)	DTXSID80972519
Chemical and physical data
Formula	C27H34O3
Molar mass	406.566 g·mol−1
3D model (JSmol)	Interactive image
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

• List of androgen esters § Testosterone esters