Estramustine

{{Short description|Chemical compound}}

{{About|a non-clinically used compound|the pharmaceutical drug|Estramustine phosphate}}

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| 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

| image = Estramustine.svg

| alt = Skeletal formula of estramustine

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| image2 = Estramustine 3D ball.png

| alt2 = Ball-and-stick model of the estramustine molecule

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| tradename = Emcyt, Estracyt

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| class = Chemotherapeutic agent; Estrogen; Estrogen ester

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 2998-57-4

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| ATC_prefix = L01

| ATC_suffix = XX11

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| PubChem = 259331

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| ChemSpiderID = 227635

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 35LT29625A

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| KEGG = D04066

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 4868

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1575

| synonyms = 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

| C=23 | H=31 | Cl=2 | N=1 | O=3

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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FRPJXPJMRWBBIH-RBRWEJTLSA-N

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Estramustine ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) is an estrogen and cytostatic antineoplastic agent which was never marketed.{{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–}}{{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–}} It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body. 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.