DT-Web

DB01299 - Sulfadoxine


Identification
Name Sulfadoxine
Accession Number DB01299
Type small molecule
Description A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 310.329
Groups approved
Monoisotopic Weight 310.073575646
Pharmacology
Indication Sulfadoxine is used in combination with pyrimethamine for the treatment or prevention of malaria. It can also be used to treat various infections in livestock as well. Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in those patients in whom chloroquine resistance is suspected.
Mechanism of action Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms Not Available
Interactions
Drug Interactions
Drug Mechanism of interaction
Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
Methotrexate The sulfamide increases the toxicity of methotrexate
Food Interactions Not Available

Targets


Dihydropteroate synthetase
Name Dihydropteroate synthetase
Gene Name Not Available
Pharmacological action yes
Actions Not Available
References
  • Raman J, Little F, Roper C, Kleinschmidt I, Cassam Y, Maharaj R, Barnes KI: Five years of large-scale dhfr and dhps mutation surveillance following the phased implementation of artesunate plus sulfadoxine-pyrimethamine in Maputo Province, Southern Mozambique. Am J Trop Med Hyg. 2010 May;82(5):788-94. - Pubmed
  • Zhang GQ, Guan YY, Zheng B, Wu S, Tang LH: Molecular assessment of Plasmodium falciparum resistance to antimalarial drugs in China. Trop Med Int Health. 2009 Oct;14(10):1266-71. - Pubmed
  • Lumb V, Das MK, Mittra P, Ahmed A, Kumar M, Kaur P, Dash AP, Singh SS, Sharma YD: Emergence of an unusual sulfadoxine-pyrimethamine resistance pattern and a novel K540N mutation in dihydropteroate synthetase in Plasmodium falciparum isolates obtained from Car Nicobar Island, India, after the 2004 Tsunami. J Infect Dis. 2009 Apr 1;199(7):1064-73. - Pubmed
DTHybrid score 1.2369
Bifunctional dihydrofolate reductase-thymidylate synthase
Name Bifunctional dihydrofolate reductase-thymidylate synthase
Gene Name Not Available
Pharmacological action unknown
Actions inhibitor
References
  • Eriksen J, Mwankusye S, Mduma S, Kitua A, Swedberg G, Tomson G, Gustafsson LL, Warsame M: Patterns of resistance and DHFR/DHPS genotypes of Plasmodium falciparum in rural Tanzania prior to the adoption of sulfadoxine-pyrimethamine as first-line treatment. Trans R Soc Trop Med Hyg. 2004 Jun;98(6):347-53. - Pubmed
  • Happi CT, Gbotosho GO, Folarin OA, Akinboye DO, Yusuf BO, Ebong OO, Sowunmi A, Kyle DE, Milhous W, Wirth DF, Oduola AM: Polymorphisms in Plasmodium falciparum dhfr and dhps genes and age related in vivo sulfadoxine-pyrimethamine resistance in malaria-infected patients from Nigeria. Acta Trop. 2005 Sep;95(3):183-93. - Pubmed
  • Fernandes NE, Cravo P, do Rosario VE: [Sulfadoxine-pyrimethamine resistance in Maputo, Mozambique: presence of mutations in the dhfr and dhps genes of Plasmodium falciparum] Rev Soc Bras Med Trop. 2007 Jul-Aug;40(4):447-50. - Pubmed
DTHybrid score 0.5652

Predictions


Id Partner name Gene Name Score
4757 Cytochrome P450 2C9 CYP2C9 0.1106
365 Dihydrofolate reductase DHFR 0.0778
2381 Dihydrofolate reductase DFR1 0.0778
2833 Dihydrofolate reductase Not Available 0.0778
2931 Dihydrofolate reductase folA 0.0778
3544 Dihydrofolate reductase folA 0.0778
3682 Dihydrofolate reductase folA 0.0778
6642 Dihydrofolate reductase folA 0.0778
6756 Dihydrofolate reductase dfrA 0.0778
3811 Cytochrome P450 19A1 CYP19A1 0.064
4924 Cytochrome P450 2C8 CYP2C8 0.0515
4119 Cytochrome P450 2D6 CYP2D6 0.0475
6013 Cytochrome P450 2E1 CYP2E1 0.0425
4512 Cytochrome P450 3A4 CYP3A4 0.0315
6016 Cytochrome P450 2C19 CYP2C19 0.0198
4200 Cytochrome P450 1A2 CYP1A2 0.0194
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