Testosterone undecylenate

Last updated
Testosterone undecylenate
Testosterone undecylenate.svg
Clinical data
Trade names Durasteron, Triolandren (mixtures)
Other namesTUe; Testosterone undecenoate; 17β-Hydroxyandrost-4-en-3-one 17β-(undec-10-enoate)
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] undec-10-enoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.045.099 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C30H46O3
Molar mass 454.695 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCCCCCCCC=C)CCC4=CC(=O)CC[C@]34C
  • InChI=1S/C30H46O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h4,21,24-27H,1,5-20H2,2-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
  • Key:PBFYIQCFOZXSKC-CNQKSJKFSA-N

Testosterone undecylenate (TUe) is an androgen/anabolic steroid medication and androgen ester which is no longer marketed. [1] [2] [3] It was a component of Durasteron and Triolandren , long-acting mixtures of testosterone esters in oil solution that were administered by intramuscular injection. [4] [5] [6] [7]

See also

Related Research Articles

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<span class="mw-page-title-main">Estradiol benzoate/estradiol dienanthate/testosterone enanthate benzilic acid hydrazone</span> Combination drug

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Testosterone propionate/testosterone valerate/testosterone undecylenate (TP/TV/TUe), sold under the brand name Triolandren, is an injectable combination medication of testosterone propionate (TP), testosterone valerate (TV), and testosterone undecylenate (TUe), which are all androgens/anabolic steroids. It contains 20 mg/mL TP, 80 mg/mL TV, and 150 mg/mL TUe in oil solution and is administered by intramuscular injection at regular intervals. The medication has been reported to have a duration of action of about 10 to 20 days.

Testosterone propionate/testosterone enanthate/testosterone undecylenate (TP/TE/TUe), sold under the brand name Durasteron, is an injectable combination medication of testosterone propionate (TP), testosterone valerate (TV), and testosterone undecylenate (TUe), all of which are androgens/anabolic steroids. It contains 20 mg TP, 80 mg TE, and 150 mg TUe in oil solution and is administered by intramuscular injection at regular intervals, for instance once every 3 or 4 weeks. Use of Durasteron by bodybuilders has been reported.

Testosterone propionate/testosterone cypionate/prasterone (TP/TC/DHEA), sold under the brand name Sten, is an injectable combination medication of testosterone propionate (TP), a fast-acting androgen/anabolic steroid, testosterone cypionate (TC), a long-acting androgen/anabolic steroid, and prasterone, an androgen and neurosteroid, which has been used to treat andropause, hypogonadism, and impotence in men and breast cancer, fibrocystic breast disease, and low sexual desire in women. It contains 25 mg TP, 75 mg TC, and 20 mg DHEA in 2 mL oil solution provided in ampoules and is administered by intramuscular injection once every 15 to 30 days. The medication was previously marketed in Mexico but appears to no longer available. The duration of action of TP/TC/DHEA has been reported to be approximately 15 to 30 days, due to the long-acting TC component.

References

  1. Shapiro S, Weinburg K, Freedman L (1956). "Notes - Long-Acting Androgens". The Journal of Organic Chemistry. 21 (11): 1300–1302. doi:10.1021/jo01117a602. ISSN   0022-3263.
  2. Gould D, Finckenor L, Hershberg EB, Cassidy J, Perlman PL (1957). "Long-acting Testosterone Esters. Some Considerations on their Biological Utilization1". Journal of the American Chemical Society. 79 (16): 4472–4475. doi:10.1021/ja01573a061. ISSN   0002-7863.
  3. US 2855341,Meier, R; Wettstein, A& Lang, E,"Testosterone compositions",published 1958-10-07, assigned to Ciba pharmaceutical Products, Inc.
  4. Schuermann H, Doepfmer R (1960). Fertilitätsstörungen beim Manne. Springer-Verlag. pp. 260–. ISBN   978-3-642-94784-1.
  5. Ufer J (1960). Hormontherapie in der Frauenheilkunde: Grundlagen und Praxis. Gruyter. p. 153. ISBN   9783111138770.
  6. Aakvaag A, Vogt JH (March 1969). "Plasma testosterone values in different forms of testosterone treatment". Acta Endocrinologica. 60 (3): 537–542. doi:10.1530/acta.0.0600537. PMID   5395873. Triolandren®, for intramuscular use, kindly supplied by Ciba, Basel, through Kobro 8c Co., Oslo, containing three different testosterone esters, in the following amounts of testosterone equivalents per ml oil: propionate 20 mg; valerate 80 mg; undecylenate 150 mg.
  7. Zachmann M, Prader A (January 1970). "Anabolic and androgenic effect of testosterone in sexually immature boys and its dependency on growth hormone". The Journal of Clinical Endocrinology and Metabolism. 30 (1): 85–95. doi:10.1210/jcem-30-1-85. PMID   4311616. Triolandren, CIBA; 250 mg of this preparation contains 20 mg of testosterone propionate, 80 mg of testosterone-n-valerianate, and 150 mg of testosterone undecylenate—250 mg thus contains 173.8 mg of testosterone; the remaining 76.2 mg consists of the ester components [...]