Chemistry:Testosterone isobutyrate

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Short description: Chemical compound
Testosterone isobutyrate
Testosterone isobutyrate.svg
Testosterone isobutyrate molecule ball.png
Clinical data
Trade namesAgovirin-Depot, Perandren M, Testocryst, Virex-Cryst
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
ATC code
Pharmacokinetic data
MetabolitesTestosterone
Duration of action~2 weeks[1][2][3]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC23H34O3
Molar mass358.522 g·mol−1
3D model (JSmol)

Testosterone isobutyrate, sold under the brand names Agovirin-Depot and Perandren M among others, is an androgen and anabolic steroid medication and a testosterone ester which is used for indications such as low testosterone levels in men and delayed puberty in boys.[1][4] It is available only in the Czech Republic and Slovakia.[1] The medication is administered by injection into muscle once every 1 to 2 weeks in males.[1] Unlike most other testosterone esters, which are provided as oil solutions, testosterone isobutyrate is formulated as a microcrystalline aqueous suspension.[1]

Medical uses

Testosterone isobutyrate is used in the treatment of hypogonadism in men and delayed puberty in adolescent boys.[1] It is also used in the treatment of Klinefelter's syndrome, aplastic anemia, Cushing's syndrome (as an anabolic to preserve lean body mass), postmenopausal osteoporosis in women, advanced breast cancer in women, breast pain in women, and cachexia.[1] Testosterone isobutyrate has been used in masculinizing hormone therapy for transgender men as well.[5][6]

Available forms

Testosterone isobutyrate is provided in the form of a 25 mg/mL microcrystalline aqueous suspension packaged in 2 mL ampoules (5 ampoules per box).[1] This equates to a dose of 50 mg per ampoule.[1] Testosterone isobutyrate (25 mg) is also available in combination with estradiol benzoate (2.5 mg) under the brand name Folivirin (1 mL ampoules).[7][8][9][10][11]

Side effects

Side effects of testosterone isobutyrate include virilization among others.[1]

Pharmacology

Testosterone isobutyrate is a prodrug of testosterone, and hence is an agonist of the androgen receptor, the biological target of endogenous androgens like testosterone and dihydrotestosterone.[1] It produces both androgenic and anabolic effects, as well as weak estrogenic effects due to metabolism of testosterone into estradiol.[1]

In contrast to most other testosterone esters, which are used as amorphous oil solutions, testosterone isobutyrate is provided in the form of a microcrystalline aqueous suspension.[1] It has very low water solubility and forms a long-lasting microcrystalline depot within muscle upon intramuscular injection.[1] This repository slowly dissolves over time.[1] As a result, testosterone isobutyrate has a prolonged duration of action of approximately 2 weeks.[1][2][3] It is administered at intervals of once every 1 to 2 weeks in men.[1] Microcrystalline testosterone isobutyrate in aqueous suspension requires a larger needle (21 gauge) than oil solutions due to the presence of solid crystals in the suspension.[1] It can produce local irritation, pain, and redness upon injection.[1]

Chemistry

Testosterone isobutyrate, or testosterone 17β-(2-methylpropanoate), is a synthetic androstane steroid and a derivative of testosterone.[12][13] It is an androgen ester; specifically, it is the C17β 2-methylpropanoate (isobutyrate) ester of testosterone.[12][13]

History

Microcrystalline testosterone isobutyrate in aqueous suspension was first described in 1952.[1][14] It was introduced for medical use shortly thereafter.[1] Around the same time, testosterone enanthate in oil solution was introduced for medical use.[1] It became the dominant long-acting injectable form of testosterone, and limited the commercial success of testosterone isobutyrate.[1] The combination of microcrystalline estradiol benzoate and testosterone isobutyrate in aqueous suspension was introduced under the brand name Femandren M by 1953.[15]

Society and culture

Brand names

Brand names of testosterone isobutyrate include Agovirin-Depot, Perandren M, Testocryst, and Virex-Cryst.[12][13][16][17] It has also been marketed in combination with estradiol benzoate under the brand names Femandren M and Folivirin.[7][8][9][10][11]

Availability

Testosterone isobutyrate is available only in the Czech Republic and Slovakia.[1][16] It was originally manufactured by the pharmaceutical company SPOFA[18] intermittently manufactured by Biotika,[1] and is now manufactured by BB Pharma.[19]

See also

  • Estradiol benzoate/testosterone isobutyrate

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 1.16 1.17 1.18 1.19 1.20 1.21 1.22 1.23 1.24 Anabolics. Molecular Nutrition Llc. 2011. pp. 314–322. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT314. 
  2. ↑ 2.0 2.1 "Fertilitätsstörungen beim Manne, Somatischer Teil". Fertilitätsstörungen beim Manne. Springer-Verlag. 13 March 2013. pp. 260–. ISBN 978-3-642-94784-1. https://books.google.com/books?id=m1iqBgAAQBAJ&pg=PA260. 
  3. ↑ 3.0 3.1 Hormontherapie in der Frauenheilkunde: Grundlagen und Praxis. Gruyter. 1960. p. 153. ISBN 9783111138770. https://books.google.com/books?id=wcRsAAAAMAAJ. 
  4. ↑ "AGOVIRIN DEPOT Injekční suspenze (Testosteroni isobutyras)". Biotika A.S.. 16 March 2011. http://www.sukl.cz/download/pil/PI15709.pdf. 
  5. ↑ "Androgen administration to transsexual women. II. Hormonal changes". Exp. Clin. Endocrinol. 88 (2): 219–23. December 1986. doi:10.1055/s-0029-1210600. PMID 3556412. 
  6. ↑ "Srovnání vylucování trí v Ceskoslovensku registrovaných androgenů" (in cs). Sbornik Lekarsky 91 (1): 16–20. January 1989. ISSN 0036-5327. PMID 2717876. 
  7. ↑ 7.0 7.1 "FOLIVIRIN Injekční suspenze (Estradioli benzoas, testosteroni isobutyras)". Biotika A.S.. 16 April 2011. http://www.sukl.cz/download/pil/PI15789.pdf. 
  8. ↑ 8.0 8.1 "Menopauzální symptomy a hormonální substituční terapie" (in cs). Praktické Lékárenství 10 (2): 68–73. 2014. ISSN 1801-2434. http://www.medvik.cz/link/bmc14059249. 
  9. ↑ 9.0 9.1 "Farmakoterapie endokrinních onemocnění a léčba kortikosteroidy" (in Czech). Farmakoterapie vnitřních nemocí: 4., zcela přepracované a doplněné vydání. Grada Publishing a.s.. 14 May 2010. pp. 380–. ISBN 978-80-247-9524-9. https://books.google.com/books?id=bUqECwAAQBAJ&pg=PA380. "In addition, testosterone isobutyrate in FOLIVIRIN, Biotika, an injection containing 25 mg testosterone isobutyrate and 2.5 mg estradiol benzoate is available. It is applied every 4-6 weeks depending on the effect." 
  10. ↑ 10.0 10.1 "Hromone". Hagers Handbuch der pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Drogisten, Ärzte u. Medizinalbeamte. Springer-Verlag. 14 December 2013. pp. 1163–. ISBN 978-3-662-36329-4. https://books.google.com/books?id=8bLwBgAAQBAJ&pg=PA1163. 
  11. ↑ 11.0 11.1 "Androgene,anabole steroide". Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL). Springer-Verlag. 29 July 2013. pp. 109, 141, 178. ISBN 978-3-662-25655-8. https://books.google.com/books?id=a2a0BgAAQBAJ&pg=PA141. 
  12. ↑ 12.0 12.1 12.2 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–642. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641. 
  13. ↑ 13.0 13.1 13.2 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA976. 
  14. ↑ "Unsere Erfahrungen mit einer neuartigen Testosteron-isobutyrat-Kristallsuspension" (in de). Dtsch. Med. Wochenschr. 77 (14): 431–2. April 1952. doi:10.1055/s-0028-1115985. PMID 12988767. 
  15. ↑ Ciba Symposium: 1953/57:Index. Ciba. 1953. p. 197. https://books.google.com/books?id=yQgbAQAAMAAJ. "Femandren M. C'est le nom des nouvelles ampoules cristallines destinées au traitement associé œs- trogène-androgène. Elles renferment, sous forme de microcristaux, 2,5 mg de mono- benzoate d'œstradiol et 50 mg d'isobutyra- te de testostérone; elles sont indiquées pour traiter les cas où il convient d'administrer simultanément de l'hormone femelle et de l'hormone mâle et où il importe aussi d'obtenir un effet prolongé, par exemple lors de symptômes d'insuffisance à la ménopause ou après castration. L'effet d'une injection se prolonge pendant 3-6 semaines" 
  16. ↑ 16.0 16.1 "Testosterone". https://www.drugs.com/international/testosterone.html. 
  17. ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. p. 270. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270. 
  18. ↑ Hormones and Brain Function. Springer Science & Business Media. 6 December 2012. p. 145. ISBN 978-1-4684-2007-4. https://books.google.com/books?id=7wX3BwAAQBAJ&pg=PA145. 
  19. ↑ "Agovirin Injection". http://www.bbpharma.sk/hormones/agovirin-injection. 

External links

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