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{{Short description|Chemical compound}} |
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{{About|a non-clinically used compound|the pharmaceutical drug|Estramustine phosphate}} |
{{About|a non-clinically used compound|the pharmaceutical drug|Estramustine phosphate}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = |
| Verifiedfields = verified |
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| Watchedfields = |
| Watchedfields = verified |
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| verifiedrevid = |
| verifiedrevid = |
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| IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-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 |
| IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-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 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = Emcyt, Estracyt |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = |
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| class = [[ |
| class = [[Chemotherapeutic agent]]; [[Estrogen (medication)|Estrogen]]; [[Estrogen ester]] |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!-- Identifiers --> |
<!-- Identifiers --> |
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| CAS_number = 2998-57-4 |
| CAS_number = 2998-57-4 |
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| CAS_supplemental = |
| CAS_supplemental = |
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| ATC_prefix = |
| ATC_prefix = L01 |
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| ATC_suffix = |
| ATC_suffix = XX11 |
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| ATC_supplemental = |
| ATC_supplemental = |
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| PubChem = 259331 |
| PubChem = 259331 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=23 | H=31 | Cl=2 | N=1 | O=3 |
| C=23 | H=31 | Cl=2 | N=1 | O=3 |
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| molecular_weight = 440.405 g/mol |
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| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl |
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
}} |
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'''Estramustine''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) is |
'''Estramustine''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) is an [[estrogen (medication)|estrogen]] and [[cytostatic]] [[antineoplastic agent]] which was never marketed.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA502|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=502–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA406|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=406–}}</ref> It is an [[estrogen ester]] – specifically, the C3 [[normustine]] [[ester]] of [[estradiol (medication)|estradiol]] – and acts in part as a [[prodrug]] of estradiol in the body.<ref name="Elks2014" /><ref name="IndexNominum2000" /> [[Estramustine phosphate]], the C17β [[phosphate]] [[ester]] of estramustine and a prodrug of estramustine, [[estromustine]], estradiol, and [[estrone (medication)|estrone]], is marketed and used in the treatment of [[prostate cancer]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> |
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==See also== |
==See also== |
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* [[Estradiol mustard]] |
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* [[List of hormonal cytostatic antineoplastic agents]] |
* [[List of hormonal cytostatic antineoplastic agents]] |
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* [[List of estrogen esters#Estradiol esters|List of estrogen esters § Estradiol esters]] |
* [[List of estrogen esters#Estradiol esters|List of estrogen esters § Estradiol esters]] |
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{{Reflist}} |
{{Reflist}} |
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{{Chemotherapeutic agents}} |
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{{Estrogen receptor modulators}} |
{{Estrogen receptor modulators}} |
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{{Androgen receptor modulators}} |
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[[Category:Abandoned drugs]] |
[[Category:Abandoned drugs]] |
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[[Category:Antiandrogens]] |
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[[Category:Antigonadotropins]] |
[[Category:Antigonadotropins]] |
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[[Category:Antineoplastic drugs]] |
[[Category:Antineoplastic drugs]] |
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[[Category:Carbamates]] |
[[Category:Carbamates]] |
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[[Category:Chloroethyl compounds]] |
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[[Category:Secondary alcohols]] |
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[[Category:Estradiol esters]] |
[[Category:Estradiol esters]] |
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[[Category:Estranes]] |
[[Category:Estranes]] |
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[[Category:Hormonal antineoplastic drugs]] |
[[Category:Hormonal antineoplastic drugs]] |
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[[Category:Human drug metabolites]] |
[[Category:Human drug metabolites]] |
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[[Category:Mitotic inhibitors]] |
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[[Category:Nitrogen mustards]] |
[[Category:Nitrogen mustards]] |
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[[Category:Organochlorides]] |
[[Category:Organochlorides]] |
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[[Category:Drugs developed by Pfizer]] |
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Latest revision as of 19:57, 20 December 2023
Clinical data | |
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Trade names | Emcyt, Estracyt |
Other names | EM; 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 class | Chemotherapeutic agent; Estrogen; Estrogen ester |
ATC code | |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.019.161 |
Chemical and physical data | |
Formula | C23H31Cl2NO3 |
Molar mass | 440.41 g·mol−1 |
3D model (JSmol) | |
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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
- Estradiol mustard
- List of hormonal cytostatic antineoplastic agents
- List of estrogen esters § Estradiol esters
References
- ^ 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.
- ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1.