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Chlorproguanil

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Chlorproguanil
Names
IUPAC name
1-[Amino-(3,4-dichloroanilino)methylidene]-2-propan-2-ylguanidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.875 Edit this at Wikidata
UNII
  • InChI=1S/C11H15Cl2N5/c1-6(2)16-10(14)18-11(15)17-7-3-4-8(12)9(13)5-7/h3-6H,1-2H3,(H5,14,15,16,17,18) ☒N
    Key: ISZNZKHCRKXXAU-UHFFFAOYSA-N ☒N
  • InChI=1/C11H15Cl2N5/c1-6(2)16-10(14)18-11(15)17-7-3-4-8(12)9(13)5-7/h3-6H,1-2H3,(H5,14,15,16,17,18)
    Key: ISZNZKHCRKXXAU-UHFFFAOYAU
  • Clc1ccc(NC(=N/C(=N/C(C)C)N)N)cc1Cl
Properties
C11H15Cl2N5
Molar mass 288.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chlorproguanil is an antimalarial drug.[1] In the late 90s and early 2000s, it was studied under collaboration with the UNICEF/UNDP/World Bank Special Program for Research and Training on Tropical Diseases and GlaxoSmithKline.[2] It was a potential alternative to the preexisting combination therapy of chloroquine and sulfadoxine/pyrimethamine, as malaria was showing drug resistance to this approach.[3] It has been trialled in combination therapy with artesunate to treat haemolysis after malaria treatment, however its development was prematurely stopped because of safety concerns secondary to its associated risk of haemolytic anaemia in individuals with glucose-6-phosphate dehydrogenase deficiency.[4][1]


References

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  1. ^ a b Fanello, Caterina I.; Karema, Corine; Avellino, Pamela; Bancone, Germana; Uwimana, Aline; Lee, Sue J.; d'Alessandro, Umberto; Modiano, David (2008). "High Risk of Severe Anaemia after Chlorproguanil-Dapsone+Artesunate Antimalarial Treatment in Patients with G6PD (A-) Deficiency". PLOS ONE. 3 (12): e4031. Bibcode:2008PLoSO...3.4031F. doi:10.1371/journal.pone.0004031. PMC 2603295. PMID 19112496.
  2. ^ Ridley, Robert G. (December 2004). "Research on infectious diseases requires better coordination". Nature Medicine. 10 (12): S137–S140. doi:10.1038/nm1153. ISSN 1546-170X. PMC 7095967. PMID 15577932. S2CID 15045454.
  3. ^ Bukirwa, H; Critchley, J (2003-07-21), "Chlorproguanil-dapsone for treating uncomplicated malaria", The Cochrane Database of Systematic Reviews, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/14651858.cd004387, retrieved 2023-12-08
  4. ^ Van Malderen, Carine; Van Geertruyden, Jean-Pierre; Machevo, Sonia; González, Raquel; Bassat, Quique; Talisuna, Ambrose; Yeka, Adoke; Nabasumba, Carolyn; Piola, Patrice; Daniel, Atwine; Turyakira, Eleanor; Forret, Pascale; Van Overmeir, Chantal; Van Loen, Harry; Robert, Annie (30 April 2012). "Glucose-6-phosphate dehydrogenase deficiency, chlorproguanil-dapsone with artesunate and post-treatment haemolysis in African children treated for uncomplicated malaria". Malaria Journal. 11 (1): 139. doi:10.1186/1475-2875-11-139. ISSN 1475-2875. PMC 3393623. PMID 22546009.

See also

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