Sulfadoxine

Chemical compound

QJ01EQ13 (WHO)

Identifiers

IUPAC name

4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide

CAS Number

2447-57-6^Y

PubChem CID

17134

DrugBank

DB01299^N

ChemSpider

16218^N

UNII

88463U4SM5

KEGG

D00580^Y

ChEMBL

ChEMBL1539^N

NIAID ChemDB

007816

CompTox Dashboard (EPA)

DTXSID6023608

ECHA InfoCard100.017.732

Chemical and physical dataFormulaC₁₂H₁₄N₄O₄SMolar mass310.33 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point190 to 194 °C (374 to 381 °F)

SMILES

COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N

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Sulfadoxine (also spelled sulphadoxine) is an ultra-long-lasting sulfonamide used in combination with pyrimethamine to treat malaria.^[1]

It is also used to prevent malaria^[2] but due to high levels of sulphadoxine-pyrimethamine resistance, this use has become less common.^[3]

It is also used, usually in combination with other drugs, to treat or prevent various infections in livestock.^{[citation needed]}

Mechanism of action

Sulfadoxine competitively inhibits dihydropteroate synthase, interfering with folate synthesis.^{[citation needed]}

References

Scholia has a topic profile for Sulfadoxine.

^ Medical Treatment - Sulphadoxine and Pyrimethamine Archived 2007-12-28 at the Wayback Machine.
^ "WHO | Intermittent preventive treatment in pregnancy (IPTp)". Who.int. Archived from the original on March 5, 2014. Retrieved 27 November 2021.
^ Matondo SI, Temba GS, Kavishe AA, et al. (2014). "High levels of sulphadoxine-pyrimethamine resistance Pfdhfr-Pfdhps quintuple mutations: a cross sectional survey of six regions in Tanzania". Malar J. 13: 152. doi:10.1186/1475-2875-13-152. PMC 3998221. PMID 24751352.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Brodimoprim
- Iclaprim^†
- Ormetoprim
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone