4-amino-N-(5-methoxypyrimidin-2-yl)benzene-1-sulfonamide

• ChemBase ID: 72766
• Molecular Formular: C11H12N4O3S
• Molecular Mass: 280.30298
• Monoisotopic Mass: 280.06301126
• SMILES: c1(ccc(cc1)S(=O)(=O)Nc1ncc(cn1)OC)N
• Canonical SMILES: COc1cnc(nc1)NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
• InChIKey: GPTONYMQFTZPKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(5-methoxypyrimidin-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: kiron; ultrax
• Synonyms: Sulfameter; Sulfamethoxydiazine; Sulfametin; Sulfametorin; Sulfameter(Bayrena); 5-Methoxysulfadiazine; SULFAMETER; N1-(5-Methoxypyrimidin-2-yl)sulfanilamide; 4-Amino-N-(5-methoxy-2-pyrimidinyl)benzenesulfonamide; 5-Methoxysulfadazine; Sulfametin, Sulfametorine; Sulfamethoxine; AHR-857; Bayrena; Durenat; Kinecid; Kiron; Koroci; Sulla; Ultrax; 5-甲氧基磺胺嘧啶; N1-(5-甲氧基嘧啶-2-基)磺胺; 磺胺对甲氧嘧啶

Database IDs

• CAS Number: 651-06-9
• EC Number: 211-480-8
• MDL Number: MFCD00006067
• Beilstein Number: 621130
• PubChem SID: 162037687; 24899422; 24870508
• PubChem CID: 5326

CALCULATED PROPERTIES

• Acid pKa: 7.056921
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.2189516
• LogD (pH = 7.4): -0.17866325
• Log P: 0.22958954
• Molar Refractivity: 70.6641 cm^3
• Polarizability: 27.140654 Å^3
• Polar Surface Area: 107.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 214-216°C

Safety Information

• Storage Condition: -20°C; 2-8°C, Desiccate; Refrigerator
• RTECS: WP0525000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C11H12N4O3S

DETAILS

MP Biomedicals - 02156708

(5-Methoxysulfadiazine)

Selleck Chemicals - S1618

Research Area: Infection
Biological Activity:
Sulfameter(Bayrena) is a long-acting sulfonamide antibacterial. It is used as a leprostatic agent in the treatment of urinary tract infections. [1]

Sigma Aldrich - S0383

Application
Sulfameter is a sulfonamide antibiotic used as a leprostatic agent and to treat urinary tract infections1. It has been investigated as a potential therapy for chloroquine-resistant malaria during pregnancy2.
Biochem/physiol Actions
Sulfameter is a sulfonamide antibiotic. Sulfonamides block the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfonamides are competitive inhibitors of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid3. Sulfameter is a dihydrofolate reductase (DHFR) inhibitor. Sulfonamides are active against Gram positive bacteria and Gram negative bacteria. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Sigma Aldrich - 46834

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

Toronto Research Chemicals - S699045

An antibacterial.

REFERENCES

• http://en.wikipedia.org/wiki/Sulfametoxydiazin
• Horstmann, et al.: Arzneim.-Forsch., 11, 682 (1961)
• Hecht, G., et al.: Arzneim.-Forsch., 11, 695 (1961)
• Bohne, et al.: Chemotherapy, 14, 195 (1969)