Sturamustine: Difference between revisions

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{{Drugbox
== Sturamustine ==
| 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


<!--Clinical data-->
[[File:Sturamustine.svg|thumb|right|Chemical structure of Sturamustine]]
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =


<!--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.
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


<!-- Identifiers -->
== Mechanism of Action ==
| 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


<!--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]].
| 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" />
== 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.
* [[List of hormonal cytostatic antineoplastic agents]]
* [[List of androgen esters]]


==References==
== Side Effects ==
{{Reflist}}


{{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 ==
[[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}}
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}}
 
Ongoing research is focused on improving the efficacy and reducing the side effects of Sturamustine. Studies are exploring its use in combination with newer targeted therapies and [[immunotherapy]] agents. Researchers are also investigating the molecular mechanisms underlying resistance to Sturamustine in certain [[cancer]] types.
 
== Related Pages ==
 
* [[Chemotherapy]]
* [[Alkylating agent]]
* [[Prostate cancer]]
* [[Breast cancer]]
* [[DNA]]
 
[[Category:Chemotherapy drugs]]
[[Category:Alkylating agents]]

Latest revision as of 10:49, 15 February 2025

Sturamustine[edit]

Chemical structure of Sturamustine

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.

Mechanism of Action[edit]

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.

Clinical Use[edit]

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.

Side Effects[edit]

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.

Pharmacokinetics[edit]

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.

Research and Development[edit]

Ongoing research is focused on improving the efficacy and reducing the side effects of Sturamustine. Studies are exploring its use in combination with newer targeted therapies and immunotherapy agents. Researchers are also investigating the molecular mechanisms underlying resistance to Sturamustine in certain cancer types.

Related Pages[edit]