Chemistry:Estradiol undecylenate

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Short description: Chemical compound
Estradiol undecylenate
Estradiol undecylenate.svg
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
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC29H42O3
Molar mass438.652 g·mol−1
3D model (JSmol)

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]

See also

References

  1. Unlisted Drugs. Pharmaceutical Section, Special Libraries Association.. 1975. ISBN 978-0-913210-02-4. https://books.google.com/books?id=txVtAAAAMAAJ. "estradiol undecylate [...] Delestrec [...] SQ 9993 [...] estradiol undecylenate [...] SH 368" 
  2. 2.0 2.1 Ringold HJ, Batres E, Rosenkranz G, "Estradiol 17-undecenoate", DE patent 1096904, published 12 January 1961, assigned to Svntex S.A.
  3. 3.0 3.1 3.2 "Drug Latentiation". Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. 1962. pp. 243–. ISBN 978-3-0348-7044-3. https://books.google.com/books?id=AYH1BwAAQBAJ&pg=PA243. "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)."