4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

• ChemBase ID: 1151
• Molecular Formular: C12H14N4O4S
• Molecular Mass: 310.32896
• Monoisotopic Mass: 310.07357595
• SMILES: S(=O)(=O)(Nc1ncnc(OC)c1OC)c1ccc(N)cc1
• Canonical SMILES: COc1c(OC)ncnc1NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
• InChIKey: PJSFRIWCGOHTNF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfadoxine
• Synonyms: Sulfadoxine; Sulphadoxine; Sulfadoxin; 4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide; N1-(5,6-Dimethoxy-4-pyrimidinyl)sulfanilamide; 4,5-Dimethoxy-6-sulfanilamidopyrimidine; 4-Sulfanilamido-5,6-dimethoxypyrimidine; Fanasil; Fanasulf; Orthosulfin; Ro 4-4393; Sanasil; Sulfadoxin; Sulforthomidine; WR 4073; 磺胺多辛

Database IDs

• CAS Number: 2447-57-6
• EC Number: 219-504-9
• MDL Number: MFCD00792890
• Beilstein Number: 625453
• PubChem SID: 160964614; 46507915; 24899765; 24870487
• PubChem CID: 17134
• ATC CODE: QJ01EQ13
• CHEMBL: 1539
• Chemspider ID: 16218
• DrugBank ID: DB01299
• KEGG ID: D00580
• Unique Ingredient Identifier: 88463U4SM5
• Wikipedia Title: Sulfadoxine

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.1161876
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.499187
• LogD (pH = 7.4): -0.2197638
• Log P: 0.58204734
• Molar Refractivity: 77.8083 cm^3
• Polarizability: 29.692802 Å^3
• Polar Surface Area: 116.43 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.72
• LOG S: -3.02
• Solubility (Water): 2.96e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 196-198°C
• Hydrophobicity(logP): 0.70 [SANGSTER (1994)]

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: DA9500000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (TLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H14N4O4S

DETAILS

DrugBank - DB01299

• Drug Groups: approved
• Description: A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]
• 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.
• Pharmacology: Sulfadoxine helps inhibit the enzyme dihydropteroate synthetase which is an enzyme necessary in the conversion of PABA to folic acid. As folic acid is vital to the synthesis, repair, and methylation of DNA which is vital to cell growth in Plasmodium falciparum. With this vital nutrient lacking, the parasite has difficulty in reproducing.

Selleck Chemicals - S2511

Research Area: Infection
Biological Activity:
Sulfadoxine(Sulphadoxine) is an ultra-long-lasting sulfonamide with an IC50 of 249 µg/ml for P. vivax. It is often used in combination with pyrimethamine to treat or prevent malaria. Both drugs are antifolates; they inhibit the production of enzymes involved in the synthesis of folic acid within the parasites. Either drug by itself is only moderately effective in treating malaria, because the parasite Plasmodium falciparum may be able to use exogenous folic acid, i.e. folic acid which is present in the parasite’s environment, while in combination, the two substances have a synergistic effect which outbalances that ability. [1][2]

Sigma Aldrich - S7821

Application
Sulfadoxine is a sulfonamide antibiotic used in combination with pyrimethamine for the treatment or prevention of malaria. It is also used to treat various infections in livestock. Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in patients where chloroquine resistance is suspected1. It is used to study infections caused by Toxoplasma gondii2 and has been used to prevent infections after surgery during animal studies3.
Biochem/physiol Actions
Sulfadoxine is a sulfonamide antibacterial that inhibits dihydropteroate synthase (DHPS), an enzyme that transforms 4-aminobenzoic acid (PABA) in the synthesis of dihydropteroic acid. This enzyme is also a component of the folate metabolic pathway and is upstream of dihydrofolate reductase (DHFR).

Sigma Aldrich - 31736

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 46810

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699070

Used as an antibacterial.

REFERENCES

• http://en.wikipedia.org/wiki/Sulfadoxine
• Kapoor, V.K., et al.: Anal. Profiles Drug Subs., 17, 571 (1988)