Sulfadoxine

Base Information

• Chemical Name: Sulfadoxine
• CAS No.: 2447-57-6
• Molecular Formula: C12H14N4O4S
• Molecular Weight: 310.334
• Hs Code.: 29350090
• European Community (EC) Number: 219-504-9
• NSC Number: 759319
• UNII: 88463U4SM5
• DSSTox Substance ID: DTXSID6023608
• Nikkaji Number: J21.373J
• Wikipedia: Sulfadoxine
• Wikidata: Q411557
• NCI Thesaurus Code: C47735
• Metabolomics Workbench ID: 43489
• ChEMBL ID: CHEMBL1539
• Mol file: 2447-57-6.mol

Synonyms:Fanasil;Ro 4 4393;Ro 4-4393;Ro 44393;Sulfadoxine;Sulformethoxine;Sulformetoxine;Sulforthomidine;Sulphormetoxin;Sulphorthodimethoxine

Chemical Property of Sulfadoxine

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 5.01E-11mmHg at 25°C
• Melting Point: 190-194 °C
• Refractive Index: 1.622
• Boiling Point: 522.8 °C at 760 mmHg
• PKA: 6.16±0.50(Predicted)
• Flash Point: 270 °C
• PSA: 124.81000
• Density: 1.441 g/cm³
• LogP: 2.61180
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol & ammonium hydroxide (9:1) at 20mg/ml
• Water Solubility.: 209.8mg/L(temperature not stated)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 310.07357611
• Heavy Atom Count: 21
• Complexity: 420

Purity/Quality:

99%-101% ^*data from raw suppliers

Sulfadoxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
• Recent EU Clinical Trials: Controlled Human Malaria Infection study to assess gametocytaemia and mosquito transmissibility in participants challenged with Plasmodium falciparum by sporozoite challenge to establish a model for the evaluation of transmission-blocking interventions
• Indications: Sulphadoxine is used only in combination with pyrimethamine for the treatment of falciparum malaria. It should generally not be used for malaria prophylaxis except perhaps in long-term travellers who have previously tolerated the combination.
• Description: Sulfadoxin is a sulfonamide antibiotic that inhibits dihydropteroate synthetase (DHPS), an enzyme involved in folic acid synthesis. Sulfadoxin competes with 4-aminobenzoate (PABA), the native substrate of DHPS, and inhibits PABA incorporation into folic acid. Folate is essential for purine and pyrimidine synthesis, therefore, sulfadoxin has antiproliferative activity in non-resistant P. falciparum. Sulfadoxin inhibits growth of P. falciparum in vitro, but potency varies between non-resistant (IC50 = 4 ng/ml) and resistant strains (IC50 = 3,970 ng/ml).
• Uses: Used as an antibacterial Used as an antibacterial.
• Therapeutic Function: Antibacterial
• Clinical Use: Sulfadoxine is used only in combination with pyrimethamine.

Technology Process of Sulfadoxine

There total 4 articles about Sulfadoxine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.4%

sodium salt of sulfanilamide (10103-15-8) + 4-chloro-5,6-dimethoxypyrimidine (5193-88-4) → sufadoxine (2447-57-6)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 85 - 90 ℃; for 4h; Reagent/catalyst; Temperature; Solvent;

Reference yield:

methanol (67-56-1) + 4-(p-aminobenzenesulfonamido)-5-methoxy-6-chloropyrimidine (5018-23-5) → sufadoxine (2447-57-6)

Guidance literature:

methanol; 4-(p-aminobenzenesulfonamido)-5-methoxy-6-chloropyrimidine; With sodium hydroxide; In Trichloroethylene; water; at 69 - 72 ℃; for 4h;

With acetic acid; at 73 - 77 ℃; pH=5.1 - 5.4;

Reference yield:

4-(3-Chloro-4-oxo-2,2-diphenyl-azetidin-1-ylamino)-N-(5,6-dimethoxy-pyrimidin-4-yl)-benzenesulfonamide → sufadoxine (2447-57-6) + 3-Chloro-4,4-diphenyl-azetidin-2-one

Guidance literature:

In N,N-dimethyl-formamide; Kinetics; Mechanism; Product distribution; electrochemical reduction at dropping mercury and glassy carbon electrodes investigated; pH 2.5-11.50;

upstream raw materials:

methanol

4-(p-aminobenzenesulfonamido)-5-methoxy-6-chloropyrimidine

sodium salt of sulfanilamide

4-chloro-5,6-dimethoxypyrimidine

Downstream raw materials:

2-{[4-(5,6-Dimethoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-hydrazono}-3-oxo-butyric acid ethyl ester

N-(5,6-dimethoxypyrimidin-4-yl)-4-(4,5,6,7-tetrafluoro-1,3-dioxo-isoindolin-2-yl)benzenesulfonamide

Refernces

• 1、 -. "Production process for sulfadoxine". Paragraph 0006; 0007. . Retrieved 2018/09/11.
• 2、 Sharma, Pratibha,Indapurkar, Priti,Mandloi, Anupam. "Synthesis and electrochemical investigations on 1--3-chloro-4,4-diphenylazetidin-2-one". . p. 494 - 497. Retrieved 2007/10/03.