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Testosterone buciclate

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Testosterone buciclate
Clinical data
Routes of
administration		Intramuscular injection
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] 4-butylcyclohexane-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H46O3
Molar mass454.684440 g/mol g·mol−1
3D model (JSmol)
  • CCCCC1CCC(CC1)C(=O)O[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C
  • InChI=1S/C30H46O3/c1-4-5-6-20-7-9-21(10-8-20)28(32)33-27-14-13-25-24-12-11-22-19-23(31)15-17-29(22,2)26(24)16-18-30(25,27)3/h19-21,24-27H,4-18H2,1-3H3/t20?,21?,24-,25-,26-,27-,29-,30-/m0/s1
  • Key:ODZDZTOROXGJAV-IRWJKHRASA-N

Testosterone buciclate (developmental code names 20 Aet-1, CDB-1781), or testosterone bucyclate, also known as testosterone 17β-(trans-4-butylcyclohexyl)carboxylate, is a synthetic, injected anabolic-androgenic steroid (AAS) that 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.[1] It 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.[1][2]

A single intramuscular injection of testosterone buciclate in an aqueous suspension has been found to produce physiological levels of testosterone within the normal range in hypogonadal men for 3 to 4 months.[1][3][4][5][6] The elimination half-life and mean residence time (average amount of time a single molecule of drug stays in the body) of testosterone buciclate were found to be 29.5 days and 60.0 days, respectively, whereas those of testosterone enanthate in castor oil were only 4.5 days and 8.5 days.[4][5][6] Testosterone buciclate also lasts longer than testosterone undecanoate, which has elimination half-lives and mean residence times of 20.9 days and 34.9 days in tea seed oil and 33.9 days and 36.0 days in castor oil, respectively.[3][5][6] In addition, there is a spike in testosterone levels with testosterone enanthate and testosterone undecanoate that is not seen with testosterone buciclate, with which levels stay highly uniform and decrease very gradually and progressively.[3]

Testosterone buciclate is able to reversibly and completely suppress spermatogenesis in men when used at sufficiently high dosages.[4] As such, the results of clinical studies for use of testosterone buciclate as a male contraceptive were promising, and trials continued as late as 1995,[7] but progress ultimately came to a standstill because the WHO was unable to find an industry partner willing to continue the development of the drug.[3] Because of this, the WHO backed away from testosterone buciclate and focused its research instead on testosterone undecanoate, which is also very long-lasting and has the advantage of having already been marketed and approved for medical use.[8]

See also

References

  1. ^ a b c C. Coutifaris; L. Mastroianni (15 August 1997). New Horizons in Reproductive Medicine. CRC Press. pp. 100–. ISBN 978-1-85070-793-6.
  2. ^ Shalender Bhasin (13 February 1996). Pharmacology, Biology, and Clinical Applications of Androgens: Current Status and Future Prospects. John Wiley & Sons. pp. 472–. ISBN 978-0-471-13320-9.
  3. ^ a b c d Eberhard Nieschlag; Hermann Behre (29 June 2013). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 316, 412. ISBN 978-3-662-04491-9.
  4. ^ a b c Anita H. Payne; Matthew P. Hardy (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN 978-1-59745-453-7.
  5. ^ a b c Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 441–446. ISBN 978-3-540-78355-8.
  6. ^ a b c Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E (1999). "Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies". Eur. J. Endocrinol. 140 (5): 414–9. PMID 10229906.
  7. ^ Behre HM, Baus S, Kliesch S, Keck C, Simoni M, Nieschlag E (1995). "Potential of testosterone buciclate for male contraception: endocrine differences between responders and nonresponders". J. Clin. Endocrinol. Metab. 80 (8): 2394–403. doi:10.1210/jcem.80.8.7543113. PMID 7543113.
  8. ^ Nieschlag E, Kumar N, Sitruk-Ware R (2013). "7α-methyl-19-nortestosterone (MENTR): the population council's contribution to research on male contraception and treatment of hypogonadism". Contraception. 87 (3): 288–95. doi:10.1016/j.contraception.2012.08.036. PMID 23063338.


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