Bropirimine: Difference between revisions

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{{Short description|An immunomodulatory drug}}
{{Drugbox
{{Drugbox
| verifiedrevid =
| verifiedfields = changed
| IUPAC_name = 2-amino-5-bromo-6-phenylpyrimidin-4(1H)-one
| verifiedrevid = 477318123
| image = Bropirimine structure.png
| IUPAC_name = 2-Amino-5-bromo-6-phenylpyrimidin-4(3H)-one
<!--Clinical data-->
| image = Bropirimine.png
| tradename =
| image2 = Bropirimine-3D-balls.png
| pregnancy_category = 
| width = 200
| legal_status = 
| width2 = 200
| routes_of_administration = 
| CAS_number = 3673-92-3
<!--Pharmacokinetic data-->
| bioavailability =
| metabolism =
| excretion = 
<!--Identifiers-->
| CAS_number = 56741-95-8
| ATC_prefix = none
| ATC_prefix = none
| DrugBank =
| PubChem = 2467
| ChEMBL = 37387
| ChemSpiderID = 2373
| ChemSpiderID = 58914
| UNII = 0T493YFU8O
| UNII_Ref = {{fdacite|correct|FDA}}
| KEGG = D03001
| UNII = J57CTF25XJ
| ChEMBL = 2104010
| synonyms =
| C=10
<!--Chemical data-->
| H=8
| C=10 | H=8 | Br=1 | N=3 | O=1
| Br=1
| molecular_weight = 266.09 g/mol
| N=3
| smiles = Br\C2=C(/c1ccccc1)N\C(=N/C2=O)N
| O=1
| StdInChI=1S/C10H8BrN3O/c11-7-8(6-4-2-1-3-5-6)13-10(12)14-9(7)15/h1-5H,(H3,12,13,14,15)
| smiles = c1ccc(cc1)c2c(=O)ncnc2N
| StdInChIKey = CIUUIPMOFZIWIZ-UHFFFAOYSA-N
| StdInChI = 1S/C10H8BrN3O/c11-7-5-6(10(15)14-8(7)12)9(13)4-2-1-3-9/h1-5H,(H3,12,14,15)
| StdInChIKey = YJZQZVOBKXQXGV-UHFFFAOYSA-N
}}
}}


'''Bropirimine''' is an experimental drug with [[anti-cancer]] and [[antiviral medicine|antiviral]] properties.{{fact|date=January 2019}} It is an orally effective [[immune modulator|immunomodulator]] and is being tried in [[bladder cancer]]s.<ref>{{cite journal |doi=10.1159/000019693 |title=Bropirimine, an Orally Active Anticancer Agent for Superficial Bladder Cancer |journal=European Urology |volume=34 |issue=2 |pages=107–110 |year=1998 |last1=Akaza |first1=Hideyuki |last2=Kotake |first2=Toshihiko |last3=Machida |first3=Toyohei }}</ref>
'''Bropirimine''' is a synthetic [[immunomodulatory drug]] that has been investigated for its potential use in the treatment of various [[cancer]]s and [[viral infections]]. It is known for its ability to induce the production of [[interferon]], a protein that plays a critical role in the body's immune response.


==Synthesis==
==Mechanism of Action==
[[File:Bropirimine synthesis.png|700px|center|thumb|Bropirimine synthesis:<ref>{{Cite journal |doi=10.1021/jm00150a018 |title=Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents |journal=Journal of Medicinal Chemistry |volume=28 |issue=12 |pages=1864–1869 |year=1985 |last1=Skulnick |first1=Harvey I. |last2=Weed |first2=Sheldon D. |last3=Eidson |first3=Emerson E. |last4=Renis |first4=Harold E. |last5=Stringfellow |first5=Dale A. |last6=Wierenga |first6=Wendell }}</ref> other syntheses:<ref name="BrownStevens1975">{{cite journal |doi=10.1039/p19750001023 |title=Triazines and related products. Part XV. 2,4-Diaminopyrimidines and 2-aminopyrimidin-4(3H)-ones bearing 1,2,3-benzotriazinyl groups as potential dihydrofolic reductase inhibitors |journal=Journal of the Chemical Society, Perkin Transactions 1 |issue=11 |pages=1023 |year=1975 |last1=Brown |first1=Thomas B. |last2=Stevens |first2=Malcolm F. G. }}</ref><ref>{{cite journal |pmid=7748456 |year=1995 |last1=Stevens |first1=M. F. |title=Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine |journal=Anti-Cancer Drug Design |volume=10 |issue=3 |pages=215–26 |last2=Baig |first2=G. U. |last3=Gate |first3=E. N. |last4=Wheelhouse |first4=R. T. }}</ref>]]
Bropirimine functions primarily as an [[immunomodulator]]. It stimulates the production of [[interferon]]-alpha, a type of [[cytokine]] that enhances the immune system's ability to fight off [[pathogens]] and [[tumor cells]]. By increasing interferon levels, bropirimine helps to activate [[natural killer cells]] and [[macrophages]], which are essential components of the [[innate immune system]].
For the first step, the dianion from malonic acid half-ester is formed by treatment with butyllithium. Acylation of the anion with benzoyl chloride proceeds at the carbanion, which is more nucleophilic (because of the higher charge density). This tricarbonyl compound decarboxylates on acidification to the β-ketoester. Condensation with guanidine leads to the pyrimidone. NBS mediated bromination then gives bropirimine.


==References==
==Clinical Applications==
{{reflist}}
Bropirimine has been studied for its potential use in treating [[bladder cancer]], particularly in cases where [[intravesical therapy]] is required. It has also been explored as a treatment for certain [[viral infections]], including those caused by the [[human papillomavirus]] (HPV).


[[Category:Experimental cancer drugs]]
===Bladder Cancer===
[[Category:Pyrimidones]]
In the context of [[bladder cancer]], bropirimine is administered intravesically, meaning it is directly instilled into the bladder. This localized delivery allows for high concentrations of the drug at the site of the tumor, potentially enhancing its effectiveness while minimizing systemic side effects.
[[Category:Organobromides]]
 
===Viral Infections===
Bropirimine's ability to induce interferon production makes it a candidate for treating viral infections. By boosting the body's natural antiviral defenses, it may help to control or reduce the severity of infections caused by viruses such as HPV.
 
==Side Effects==
The use of bropirimine can be associated with several side effects, primarily due to its immunostimulatory effects. Common side effects include [[flu-like symptoms]], such as [[fever]], [[chills]], [[fatigue]], and [[muscle aches]]. These symptoms are generally mild and resolve after discontinuation of the drug.
 
==Research and Development==
Bropirimine has been the subject of various clinical trials aimed at evaluating its efficacy and safety in different therapeutic contexts. While promising results have been observed in some studies, further research is needed to fully establish its clinical utility and to optimize its dosing regimens.


==Related Pages==
* [[Immunotherapy]]
* [[Interferon]]
* [[Bladder cancer]]
* [[Viral infection]]


{{antineoplastic-drug-stub}}
[[Category:Immunomodulatory drugs]]
{{dictionary-stub1}}
[[Category:Antiviral drugs]]
[[Category:Experimental cancer drugs]]

Revision as of 19:16, 22 March 2025

An immunomodulatory drug


Bropirimine
File:Bropirimine.png
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number 3673-92-3
PubChem 2467
DrugBank
ChemSpider 2373
KEGG D03001


Bropirimine is a synthetic immunomodulatory drug that has been investigated for its potential use in the treatment of various cancers and viral infections. It is known for its ability to induce the production of interferon, a protein that plays a critical role in the body's immune response.

Mechanism of Action

Bropirimine functions primarily as an immunomodulator. It stimulates the production of interferon-alpha, a type of cytokine that enhances the immune system's ability to fight off pathogens and tumor cells. By increasing interferon levels, bropirimine helps to activate natural killer cells and macrophages, which are essential components of the innate immune system.

Clinical Applications

Bropirimine has been studied for its potential use in treating bladder cancer, particularly in cases where intravesical therapy is required. It has also been explored as a treatment for certain viral infections, including those caused by the human papillomavirus (HPV).

Bladder Cancer

In the context of bladder cancer, bropirimine is administered intravesically, meaning it is directly instilled into the bladder. This localized delivery allows for high concentrations of the drug at the site of the tumor, potentially enhancing its effectiveness while minimizing systemic side effects.

Viral Infections

Bropirimine's ability to induce interferon production makes it a candidate for treating viral infections. By boosting the body's natural antiviral defenses, it may help to control or reduce the severity of infections caused by viruses such as HPV.

Side Effects

The use of bropirimine can be associated with several side effects, primarily due to its immunostimulatory effects. Common side effects include flu-like symptoms, such as fever, chills, fatigue, and muscle aches. These symptoms are generally mild and resolve after discontinuation of the drug.

Research and Development

Bropirimine has been the subject of various clinical trials aimed at evaluating its efficacy and safety in different therapeutic contexts. While promising results have been observed in some studies, further research is needed to fully establish its clinical utility and to optimize its dosing regimens.

Related Pages