Estramustine

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
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
Trade namesEmcyt, Estracyt
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
ATC code
Identifiers
  • [(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
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC23H31Cl2NO3
Molar mass440.41 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:FRPJXPJMRWBBIH-RBRWEJTLSA-N checkY

Estramustine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name) is an estrogen and cytostatic antineoplastic agent which was never marketed.[1][2] It is a carbamate derivative 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]

Synthesis

[edit | edit source]

Estramustine is a carbamate derivative of the natural hormone, estradiol. The amine (ClCH2CH2)2NH is treated with phosgene to give the acid chloride of normustine. This reacts with the phenolic hydroxyl group of estradiol in the presence of a base to give estramustine.[3][4]

See also

[edit | edit source]

References

[edit | edit source]
  1. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

This article about an estrane is a stub. You can help Wikipedia by expanding it.

Stub icon

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

Retrieved from "http://70.231.62.181/index.php?title=Estramustine&oldid=6945114"