Testosterone undecylenate

Testosterone undecylenate
Clinical data
Trade names	Durasteron, Triolandren (mixtures)
Other names	TUe; 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
	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] undec-10-enoate;
CAS Number	29430-26-0 ;
PubChem CID	9846790;
ChemSpider	21229627;
UNII	KU65V22IOU;
CompTox Dashboard (EPA)	DTXSID10951953 ;
ECHA InfoCard	100.045.099
Chemical and physical data
Formula	C30H46O3
Molar mass	454.695 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCCCCCCCC=C)CCC4=CC(=O)CC[C@]34C;
	InChI 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]

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[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 [...]

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[ShapiroWeinburg1956-1] [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.

[GouldFinckenor1957-2] [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.

[US2855341A-3] [3]
US 2855341, Meier, R; Wettstein, A & Lang, E, "Testosterone compositions", published 1958-10-07, assigned to Ciba pharmaceutical Products, Inc.

[SchuermannDoepfmer1960-4] [4]
Schuermann H, Doepfmer R (1960). Fertilitätsstörungen beim Manne. Springer-Verlag. pp. 260–. ISBN 978-3-642-94784-1.

[Ufer1960-5] [5]
Ufer J (1960). Hormontherapie in der Frauenheilkunde: Grundlagen und Praxis. Gruyter. p. 153. ISBN 9783111138770.

[pmid5395873-6] [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.

[ZachmannPrader1970-7] [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 [...]

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