Estradiol undecylenate

Estradiol undecylenate (EUe; developmental code name SH-368)[1] is an estrogen medication and estrogen ester which was never marketed.[2] It is the C17β undecenoate (undecylenate) ester of estradiol.[2] Following an intramuscular injection, EUe has a very prolonged effect, exceeding that of other estradiol esters like estradiol valerate and estradiol enanthate.[3] Due to its very long duration of action, EUe releases only subthreshold amounts of estradiol at conventional doses.[3] However, this may still be useful in menopausal hormone therapy.[3]

Not to be confused with Estradiol undecylate.
Estradiol undecylenate
Clinical data
Other namesSH-368; Estradiol undecenoate; Estra-1,3,5(10)-triene-3,17β-diol 17β-(10-undecenoate)
Routes of
administration		Intramuscular injection
Drug classEstrogen; Estrogen ester
Identifiers
IUPAC name
  • [(8R,9S,13S,14S,17S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] undec-10-enoate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.080.203
Chemical and physical data
FormulaC29H42O3
Molar mass438.652 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCCCCCCCC=C)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C29H42O3/c1-3-4-5-6-7-8-9-10-11-28(31)32-27-17-16-26-25-14-12-21-20-22(30)13-15-23(21)24(25)18-19-29(26,27)2/h3,13,15,20,24-27,30H,1,4-12,14,16-19H2,2H3/t24-,25-,26+,27+,29+/m1/s1
  • Key:VJTIEHBTPQORML-GVGNIZHQSA-N

See also

References
  1. Unlisted Drugs. Pharmaceutical Section, Special Libraries Association. 1975. ISBN 978-0-913210-02-4. estradiol undecylate [...] Delestrec [...] SQ 9993 [...] estradiol undecylenate [...] SH 368
  2. DE 1096904, Ringold HJ, Batres E, Rosenkranz G, "Estradiol 17-undecenoate", published 12 January 1961, assigned to Svntex S.A.
  3. Harper NJ (1962). "Drug Latentiation". In Jucker E (ed.). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 243–. ISBN 978-3-0348-7044-3. Retarded estrogens. In animal experiments it has been shown esterification at C-17 results in longer retarding effects than esterification at C-3. The optimal retarding effect (exceeding 29 days) may be obtained with the C-17 oenanthate. However, the effect exceeds the time interval of 28 days normally considered sufficient for the treatment of a female during one period and for this reason the shorter active estradiol-17-valerianate has been introduced. The estradiol undecylenate has a more protracted effect but it releases only subthreshold doses of steroid (advantage may be taken of this for the treatment of menopause).


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