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-{{Drugbox
+== Sturamustine ==
-<!--Clinical data-->
+[[File:Sturamustine.svg|thumb|right|Chemical structure of Sturamustine]]
-<!--Pharmacokinetic data-->
+'''Sturamustine''' is a [[chemotherapy]] drug that belongs to the class of [[alkylating agents]]. It is primarily used in the treatment of certain types of [[cancer]], including [[prostate cancer]] and [[breast cancer]]. Sturamustine is a [[nitrogen mustard]] derivative, which means it works by interfering with the [[DNA]] replication process in [[cancer cells]], ultimately leading to cell death.
-<!-- Identifiers -->
+== Mechanism of Action ==
-<!--Chemical data-->
+Sturamustine functions by forming cross-links between [[DNA strands]], which prevents the [[DNA]] from being properly replicated and transcribed. This action is typical of [[alkylating agents]], which are known for their ability to add alkyl groups to the [[DNA]] molecule. The cross-linking of [[DNA]] strands inhibits the [[cell cycle]], particularly affecting rapidly dividing [[cancer cells]].
-'''Sturamustine''', also known as '''dehydroepiandrosterone (DHEA) 17β-''N''-(2-chloroethyl)-''N''-nitrosourea''', is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and a C17β [[nitrosourea]] conjugate of [[dehydroepiandrosterone]] (DHEA) which was developed as a [[cytostatic]] [[antineoplastic agent]] (i.e., a [[chemotherapy drug]]) for the treatment of [[hormone-sensitive cancer|hormone-dependent]] [[tumor]]s but was never marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA1122|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=1122}}</ref><ref name="pmid7071885">{{cite journal | vauthors = Chavis C, de Gourcy C, Borgna JL, Imbach JL | title = New steroidal nitrosoureas | journal = Steroids | volume = 39 | issue = 2 | pages = 129–47 | year = 1982 | pmid = 7071885 | doi = | url = }}</ref> It was [[chemical synthesis|synthesized]] in 1982.<ref name="Elks2014" /><ref name="pmid7071885" />
+== Clinical Use ==
-==See also==
+Sturamustine is used in the treatment of hormone-refractory [[prostate cancer]] and [[breast cancer]] that has not responded to other forms of treatment. It is often administered in combination with other [[chemotherapy]] agents to enhance its effectiveness. The drug is typically given intravenously, and the dosage depends on the patient's overall health, the type of [[cancer]], and the stage of the disease.
-==References==
+== Side Effects ==
-{{Androgen receptor modulators}}
+Like many [[chemotherapy]] drugs, Sturamustine can cause a range of side effects. Common side effects include [[nausea]], [[vomiting]], [[hair loss]], and [[myelosuppression]], which is a decrease in the production of blood cells. Patients may also experience [[fatigue]], [[diarrhea]], and an increased risk of [[infection]] due to lowered [[white blood cell]] counts.
-[[Category:Abandoned drugs]]
+== Pharmacokinetics ==
-{{Genito-urinary-drug-stub}}
+Sturamustine is metabolized in the [[liver]] and excreted primarily through the [[kidneys]]. The drug's half-life and clearance rate can vary depending on the patient's [[liver function]] and [[renal function]]. Monitoring of [[blood cell]] counts and [[liver function tests]] is essential during treatment to adjust dosages and prevent toxicity.
-{{Antineoplastic-drug-stub}}
-{{Steroid-stub}}
+== Research and Development ==
-{{dictionary-stub1}}

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2024-02-25T13:04:26Z

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{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = ''N''-(2-chloroethyl)-''N<nowiki>'</nowiki>''-[(3β,17β)-3-hydroxyandrost-5-en-17-yl]-''N''-nitrosocarbamimidic acid
| image = Sturamustine.svg
| width = 250px


| tradename =
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref =
| CAS_number = 81912-55-2
| CAS_supplemental =
| class =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem =
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 57260288
| UNII =
| KEGG =
| ChEBI =
| ChEMBL =
| synonyms = Dehydroepiandrosterone (DHEA) 17β-''N''-(2-chloroethyl)-''N''-nitrosourea; ''N''-(2-Chloroethyl)-''N<nowiki>'</nowiki>''-(3-hydroxyandrost-5-en-17-yl)-''N''-nitrosourea


| C=22 | H=34 | Cl=1 | N=3 | O=3
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2/N=C(/N(CCCl)N=O)\O)CC=C4[C@@]3(CC[C@@H](C4)O)C
| StdInChI_Ref =
| StdInChI = 1S/C22H34ClN3O3/c1-21-9-7-15(27)13-14(21)3-4-16-17-5-6-19(22(17,2)10-8-18(16)21)24-20(28)26(25-29)12-11-23/h3,15-19,27H,4-13H2,1-2H3,(H,24,28)/t15-,16-,17-,18-,19-,21-,22-/m0/s1
| StdInChIKey_Ref =
| StdInChIKey = QSHCCJGNLACWQQ-UMWWKMARSA-N
}}

'''Sturamustine''', also known as '''dehydroepiandrosterone (DHEA) 17β-''N''-(2-chloroethyl)-''N''-nitrosourea''', is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and a C17β [[nitrosourea]] conjugate of [[dehydroepiandrosterone]] (DHEA) which was developed as a [[cytostatic]] [[antineoplastic agent]] (i.e., a [[chemotherapy drug]]) for the treatment of [[hormone-sensitive cancer|hormone-dependent]] [[tumor]]s but was never marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA1122|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=1122}}</ref><ref name="pmid7071885">{{cite journal | vauthors = Chavis C, de Gourcy C, Borgna JL, Imbach JL | title = New steroidal nitrosoureas | journal = Steroids | volume = 39 | issue = 2 | pages = 129–47 | year = 1982 | pmid = 7071885 | doi = | url = }}</ref> It was [[chemical synthesis|synthesized]] in 1982.<ref name="Elks2014" /><ref name="pmid7071885" />

==See also==
* [[List of hormonal cytostatic antineoplastic agents]]
* [[List of androgen esters]]

==References==
{{Reflist}}

{{Androgen receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Androgens and anabolic steroids]]
[[Category:Androstanes]]
[[Category:Antineoplastic drugs]]
[[Category:Experimental cancer drugs]]
[[Category:Nitrosoureas]]
[[Category:Organochlorides]]
[[Category:Prodrugs]]
[[Category:Steroid esters]]
[[Category:Chloroethyl compounds]]

{{Genito-urinary-drug-stub}}
{{Antineoplastic-drug-stub}}
{{Steroid-stub}}
{{dictionary-stub1}}

Sturamustine - Revision history

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Prab: CSV import