Testosterone phenylacetate

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Testosterone phenylacetate
Testosterone phenylacetate.svg
Clinical data
Trade names Perandren, Androject
Other namesTPA
Routes of
administration
Intramuscular injection
Drug class Androgen; Anabolic steroid; Androgen ester
Identifiers
  • [(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
Formula C27H34O3
Molar mass 406.557 g·mol−1
3D model (JSmol)
  • 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=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 [4] However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.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

Related Research Articles

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Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate/testosterone decanoate (TP/TPP/TiC/TD), also known as a Sustanon 250 (Organon), is an injectable combination medication of four testosterone esters, all of which are androgens/anabolic steroids.

<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

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<span class="mw-page-title-main">Testosterone propionate</span> Chemical compound

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<span class="mw-page-title-main">Estradiol benzoate</span> Chemical compound

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<span class="mw-page-title-main">Estradiol cypionate</span> Chemical compound

Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for trans women, and in hormonal birth control for women. It is given by injection into muscle once every 1 to 4 weeks.

<span class="mw-page-title-main">Estradiol dienantate</span> Chemical compound

Estradiol dienanthate (EDE), sold under the brand names Climacteron among others, is a long-acting estrogen medication which was previously used in menopausal hormone therapy for women and to suppress lactation in women. It was formulated in combination with estradiol benzoate (EB), a short-acting estrogen, and testosterone enanthate benzilic acid hydrazone (TEBH), a long-acting androgen/anabolic steroid. EDE has not been made available for medical use alone. The medication, in combination with EB and TEBH, was given by injection into muscle once or at regular intervals, for instance once every 6 weeks.

<span class="mw-page-title-main">Steroid ester</span> Class of chemical compounds

A steroid ester is an ester of a steroid. They include androgen esters, estrogen esters, progestogen esters, and corticosteroid esters. Steroid esters may be naturally occurring/endogenous like DHEA sulfate or synthetic like estradiol valerate. Esterification is useful because it is often able to render the parent steroid into a prodrug of itself with altered chemical properties such as improved metabolic stability, water solubility, and/or lipophilicity. This, in turn, can enhance pharmacokinetics, for instance by improving the steroid's bioavailability and/or conferring depot activity and hence an extended duration with intramuscular or subcutaneous injection.

<span class="mw-page-title-main">Testosterone isobutyrate</span> Chemical compound

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<span class="mw-page-title-main">Nandrolone hexyloxyphenylpropionate</span> Chemical compound

Nandrolone hexyloxyphenylpropionate, also known as 19-nortestosterone 17β-(3- phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey. It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication. Approximately 70% of men became azoospermic, while the remaining men all became oligospermic. NHPP has a mean residence time in the body of 29.1 days and an elimination half-life in the body of 20.1 days.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

<span class="mw-page-title-main">Testosterone buciclate</span> Chemical compound

Testosterone buciclate is a synthetic, injected anabolic–androgenic steroid (AAS) which was never marketed. It was developed in collaboration by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and the World Health Organization (WHO) in the 1970s and early 1980s for use in androgen replacement therapy for male hypogonadism and as a potential male contraceptive. It was first described in 1986. The medication is an androgen ester – specifically, the C17β buciclate (4-butylcyclohexane-1-carboxylate) ester of testosterone – and is a prodrug of testosterone with a very long duration of action when used as a depot via intramuscular injection. Testosterone buciclate is formulated as a microcrystalline aqueous suspension with a defined particle size of at least 75% in the range of 10 to 50 μm.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Pharmacokinetics of estradiol</span>

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<span class="mw-page-title-main">Estradiol benzoate/progesterone</span> Drug combination

Estradiol benzoate/progesterone (EB/P4), sold under the brand names Duogynon and Sistocyclin among others, is a combination medication of estradiol benzoate (EB), an estrogen, and progesterone (P4), a progestogen. It has been formulated both as short-acting oil solutions and long-acting microcrystalline aqueous suspensions and is given by injection into muscle either once or continuously at regular intervals.

<span class="mw-page-title-main">Pharmacokinetics of testosterone</span>

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<span class="mw-page-title-main">Testosterone undecylenate</span> Chemical compound

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Estrone/progesterone/testosterone (E1/P4/T), sold under the brand name Tristeron or Tristerone, is an injectable combination medication of estrone (E1), an estrogen, progesterone (P4), a progestogen, and testosterone (T), an androgen/anabolic steroid, which was used in the treatment of functional uterine bleeding in women. It contained 6 mg estrone, 50 mg progesterone, and 25 mg testosterone in microcrystalline aqueous suspension and was administered by intramuscular injection. The medication was manufactured by Wyeth and was marketed by 1951. It is no longer available.

References

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  6. 1 2 Chatton MJ (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–.
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  10. Lisser H, Escamilla RF (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". Journal of the American Geriatrics Society. 2 (5): 293–298. doi:10.1111/j.1532-5415.1954.tb00207.x. PMID   13162731. S2CID   39965563.
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