Chlorproguanil

Chlorproguanil

Names
IUPAC name 1-[Amino-(3,4-dichloroanilino)methylidene]-2-propan-2-ylguanidine
Identifiers
CAS Number	537-21-3  Y
3D model (JSmol)	Interactive image
ChemSpider	20950  N
ECHA InfoCard	100.007.875
PubChem CID	22323
UNII	8O3249M729  Y
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) 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
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). N  verify  (what is  YN ?) 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

1. 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

• Proguanil
• Chlorproguanil hydrochloride-dapsone-artesunate