Chlorproguanil

Chlorproguanil
Names
	IUPAC name 1-[Amino-(3,4-dichloroanilino)methylidene]-2-propan-2-ylguanidine
Identifiers
CAS Number	537-21-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	20950 ;
ECHA InfoCard	100.007.875
PubChem CID	22323;
UNII	8O3249M729 ;
CompTox Dashboard (EPA)	DTXSID5022807 ;
	InChI 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) Key: ISZNZKHCRKXXAU-UHFFFAOYSA-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;
	SMILES Clc1ccc(NC(=N/C(=N/C(C)C)N)N)cc1Cl;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

^ ^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.
^ 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.
^ 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
^ 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.