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Estramustine

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This article is about a non-clinically used compound. For the pharmaceutical drug, see Estramustine phosphate.

Estramustine
Skeletal formula of estramustine
Ball-and-stick model of the estramustine molecule
Clinical data
Other namesEM; EaM; Leo 275; Ro 21-8837; Estradiol 3-(bis(2-chloroethyl)carbamate) ester; Estra-1,3,5(10)-triene-3,17β-diol 3-(bis(2-chloroethyl)carbamate) ester
Drug classChemotherapeutic agent; Estrogen; Estrogen ester
Identifiers

IUPAC name

  • [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate

CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.161 Edit this at Wikidata
Chemical and physical data
FormulaC23H31Cl2NO3
Molar mass440.41 g·mol−1
3D model (JSmol)

SMILES

  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl

  • InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1 check

  • Key:FRPJXPJMRWBBIH-RBRWEJTLSA-N check

Estramustine (INN, USAN, BAN) is an estrogen and cytostatic antineoplastic agent which was never marketed.[1][2] It is an estrogen ester – specifically, the C3 normustine ester of estradiol – and acts in part as a prodrug of estradiol in the body.[1][2] Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer.[1][2]

See also

  • List of hormonal cytostatic antineoplastic agents
  • List of estrogen esters § Estradiol esters

References

  1. ^ a b c Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 502–. ISBN 978-1-4757-2085-3.
  2. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1.

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