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| {{Short description|Chemical compound}} | | {{Short description|A chemotherapy medication used in the treatment of prostate cancer}} |
| {{About|a non-clinically used compound|the pharmaceutical drug|Estramustine phosphate}}
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| {{cs1 config|name-list-style=vanc|display-authors=6}}
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| {{Drugbox | | {{Drugbox |
| | Verifiedfields = verified | | | Verifiedfields = changed |
| | Watchedfields = verified
| | | verifiedrevid = 477002679 |
| | verifiedrevid = | | | IUPAC_name = [(4R,5S,6S,8R,9S,10S,13S,14S,17S)-6,9,14-trihydroxy-10,13-dimethyl-3-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16,17-hexadecahydrocyclopenta[a]phenanthren-17-yl] N-carbamoyloxycarbamate |
| | 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 | | | image = Estramustine.png |
| | image = Estramustine.svg | | | width = 200 |
| | alt = Skeletal formula of estramustine
| | }} |
| | width = 250px | |
| | image2 = Estramustine 3D ball.png
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| | alt2 = Ball-and-stick model of the estramustine molecule
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| | width2 = 250px
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| <!--Clinical data-->
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| | tradename = Emcyt, Estracyt
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| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| | pregnancy_US = <!-- A / B / C / D / X -->
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| | pregnancy_category =
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| | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| | legal_CA =
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| | legal_UK =
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| | legal_US =
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| | legal_status =
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| | routes_of_administration =
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| | class = [[Chemotherapeutic agent]]; [[Estrogen (medication)|Estrogen]]; [[Estrogen ester]]
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| <!--Pharmacokinetic data-->
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| | bioavailability =
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| | protein_bound =
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| | metabolism =
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| | excretion =
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| <!-- Identifiers -->
| | '''Estramustine''' is a [[chemotherapy]] medication primarily used in the treatment of [[prostate cancer]]. It is a combination of [[estradiol]] and [[nitrogen mustard]], designed to target cancer cells by disrupting their growth and division. Estramustine is unique in its dual action as both a [[hormonal therapy]] and a [[cytotoxic agent]]. |
| | CAS_number_Ref = {{cascite|correct|??}}
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| | CAS_number = 2998-57-4
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| | CAS_supplemental =
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| | ATC_prefix = L01
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| | ATC_suffix = XX11
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| | ATC_supplemental =
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| | PubChem = 259331
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| | IUPHAR_ligand =
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| | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
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| | DrugBank =
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| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID = 227635
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| | UNII_Ref = {{fdacite|correct|FDA}}
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| | UNII = 35LT29625A
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| | KEGG_Ref = {{keggcite|correct|kegg}}
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| | KEGG = D04066
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| | ChEBI_Ref = {{ebicite|correct|EBI}}
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| | ChEBI = 4868
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| | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| | ChEMBL = 1575
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| | 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
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| <!--Chemical data-->
| | ==Mechanism of Action== |
| | C=23 | H=31 | Cl=2 | N=1 | O=3
| | Estramustine works by combining the properties of [[estrogen]] and [[alkylating agents]]. The estrogen component helps in reducing the levels of [[testosterone]], a hormone that can promote the growth of prostate cancer cells. The alkylating agent, derived from nitrogen mustard, interferes with the DNA replication process in cancer cells, leading to cell death. |
| | 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}}
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| | 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
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| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChIKey = FRPJXPJMRWBBIH-RBRWEJTLSA-N
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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 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 a [[carbamate]] derivative of [[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" />
| | ==Pharmacokinetics== |
| ==Synthesis==
| | Estramustine is administered orally and is absorbed in the gastrointestinal tract. Once in the body, it is metabolized into its active forms, estramustine and estradiol, which exert their effects on cancer cells. The drug is primarily excreted through the urine. |
| Estramustine is a [[carbamate]] derivative of the natural hormone, [[estradiol]]. The [[amine]] {{chem2|(ClCH2CH2)2NH}} is treated with [[phosgene]] to give the [[acid chloride]] of [[normustine]]. This reacts with the [[phenol|phenolic hydroxyl group]] of estradiol in the presence of a [[base (chemistry)|base]] to give estramustine.<ref>{{cite journal | vauthors = Niculescu-Duvăz I, Cambanis A, Tărnăuceanu E | title = Potential anticancer agents. II. Urethan-type nitrogen mustards of some natural sex hormones | journal = Journal of Medicinal Chemistry | volume = 10 | issue = 2 | pages = 172–174 | date = March 1967 | pmid = 6034059 | doi = 10.1021/jm00314a009 }}</ref><ref>{{cite journal | vauthors = Sk UH, Dixit D, Sen E | title = Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation | journal = European Journal of Medicinal Chemistry | volume = 68 | pages = 47–57 | date = October 2013 | pmid = 23954240 | doi = 10.1016/j.ejmech.2013.07.007 }}</ref>
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| == See also == | | ==Clinical Use== |
| * [[Estradiol mustard]]
| | Estramustine is indicated for the treatment of [[metastatic prostate cancer]], particularly in cases where the cancer has become resistant to other forms of [[hormonal therapy]]. It is often used in combination with other chemotherapy agents to enhance its efficacy. |
| * [[List of hormonal cytostatic antineoplastic agents]]
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| * [[List of estrogen esters#Estradiol esters|List of estrogen esters § Estradiol esters]]
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| == References == | | ==Side Effects== |
| {{Reflist}}
| | Common side effects of estramustine include nausea, vomiting, and diarrhea. Patients may also experience [[gynecomastia]], [[edema]], and [[hypertension]]. Due to its estrogenic activity, there is a risk of [[thromboembolic events]], such as [[deep vein thrombosis]] and [[pulmonary embolism]]. |
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| {{Chemotherapeutic agents}}
| | ==Contraindications== |
| {{Estrogen receptor modulators}}
| | Estramustine is contraindicated in patients with a history of [[thromboembolic disorders]], severe [[liver disease]], or known hypersensitivity to the drug. It should not be used in pregnant or breastfeeding women due to potential harm to the fetus or infant. |
| {{Androgen receptor modulators}}
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| [[Category:Abandoned drugs]]
| | ==Related Pages== |
| [[Category:Antiandrogens]]
| | * [[Prostate cancer]] |
| [[Category:Antigonadotropins]]
| | * [[Chemotherapy]] |
| [[Category:Antineoplastic drugs]]
| | * [[Hormonal therapy]] |
| [[Category:Carbamates]] | | * [[Alkylating agents]] |
| [[Category:Chloroethyl compounds]] | |
| [[Category:Secondary alcohols]] | |
| [[Category:Estradiol esters]]
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| [[Category:Estranes]]
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| [[Category:Estrogens]]
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| [[Category:Hormonal antineoplastic drugs]]
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| [[Category:Human drug metabolites]]
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| [[Category:Mitotic inhibitors]]
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| [[Category:Nitrogen mustards]]
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| [[Category:Organochlorides]]
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| [[Category:Drugs developed by Pfizer]] | |
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| {{Steroid-stub}}
| | [[Category:Chemotherapy]] |
| {{Antineoplastic-drug-stub}}
| | [[Category:Hormonal therapy]] |
| == Estramustine ==
| | [[Category:Prostate cancer treatments]] |
| <gallery>
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| File:Estramustine.svg|Estramustine
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| File:Estramustine 3D ball.png|Estramustine 3D Ball Model
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| </gallery>
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A chemotherapy medication used in the treatment of prostate cancer
Estramustine is a chemotherapy medication primarily used in the treatment of prostate cancer. It is a combination of estradiol and nitrogen mustard, designed to target cancer cells by disrupting their growth and division. Estramustine is unique in its dual action as both a hormonal therapy and a cytotoxic agent.
Mechanism of Action
Estramustine works by combining the properties of estrogen and alkylating agents. The estrogen component helps in reducing the levels of testosterone, a hormone that can promote the growth of prostate cancer cells. The alkylating agent, derived from nitrogen mustard, interferes with the DNA replication process in cancer cells, leading to cell death.
Pharmacokinetics
Estramustine is administered orally and is absorbed in the gastrointestinal tract. Once in the body, it is metabolized into its active forms, estramustine and estradiol, which exert their effects on cancer cells. The drug is primarily excreted through the urine.
Clinical Use
Estramustine is indicated for the treatment of metastatic prostate cancer, particularly in cases where the cancer has become resistant to other forms of hormonal therapy. It is often used in combination with other chemotherapy agents to enhance its efficacy.
Side Effects
Common side effects of estramustine include nausea, vomiting, and diarrhea. Patients may also experience gynecomastia, edema, and hypertension. Due to its estrogenic activity, there is a risk of thromboembolic events, such as deep vein thrombosis and pulmonary embolism.
Contraindications
Estramustine is contraindicated in patients with a history of thromboembolic disorders, severe liver disease, or known hypersensitivity to the drug. It should not be used in pregnant or breastfeeding women due to potential harm to the fetus or infant.
Related Pages
