4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide

• ChemBase ID: 1362
• Molecular Formular: C12H14N4O2S
• Molecular Mass: 278.33016
• Monoisotopic Mass: 278.08374671
• SMILES: S(=O)(=O)(Nc1nc(cc(n1)C)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nc(C)cc(n1)C
• InChI: InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
• InChIKey: ASWVTGNCAZCNNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide; sulfamethazine
• Synonyms: Sulfamethazine; Sulfamethazine; Sulphadimidine; Sulphamezathine; Sulfadimesine; Sulfadimethylpyrimidine; Sulfadimezine; Superseptil; Sulfodimezine; Sulphamethazine; Sulfadimidine; 4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide; N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide; Sulfamethazine; 4,6-Dimethylsulfadiazine; 4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide; Sulfadimidine; Azolmetazin; Sulfamezathine; Sulfadimerazine; Diazil; 4,6-二甲基磺胺嘧啶; 4-氨基-N-(4,6-二甲基-2-嘧啶基)苯磺酰胺; 磺胺二甲嘧啶; 磺胺二甲基嘧啶

Database IDs

• CAS Number: 57-68-1; 1981-58-4
• EC Number: 200-346-4
• MDL Number: MFCD00006066
• Beilstein Number: 261304
• PubChem SID: 24899686; 46507146; 24870458; 160964822
• PubChem CID: 5327

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.99357
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.63772017
• LogD (pH = 7.4): 0.21068367
• Log P: 0.65000117
• Molar Refractivity: 73.3839 cm^3
• Polarizability: 28.103605 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.43
• LOG S: -3.08
• Solubility (Water): 2.30e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.5 mg/mL at 29 oC [MERCK INDEX (1983); at pH 7]; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 192-202°C; 198-200°C; 198-201°C
• Hydrophobicity(logP): 0.89 [BIOBYTE (1995)]

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• RTECS: WO9275000
• German water hazard class: 2
• Safety Statements: 24/25
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Mechanism of Action: Dihydrofolate-reductase inhibitor; Dihydrofolate-synthesis inhibitor; Folate-antagonist; Subsequent reduction in the level of folic acid reduced the production of nucleic acids in sensitive bacteria.; Sulfonamides, being structural analogues of para-aminobenzoic acid (PABA), competitively inhibit the incorporation of PABA into dihydropteric acid, the precursor of folic acid.

Product Information

• Purity: ~99%; ≥99%; 99%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Application(s): Antiseptic; Low acute toxicity; Widely-used, short acting sulfonamide, used in treatment of systemic and urinary tract infections
• Empirical Formula (Hill Notation): C12H14N4O2S

DETAILS

MP Biomedicals - 05210468

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102986

Crystalline
Purity: ~99%

DrugBank - DB01582

• Drug Groups: approved
• Description: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides. [PubChem]
• Indication: For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
• Pharmacology: Sulfamethazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.
• Toxicity: Sulfamethazine may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
• Absorption: Rapidly absorbed following oral administration.

Sigma Aldrich - S6256

Biochem/physiol Actions
An antimicrobial sulfur drug. Induces CYP3A4 expression and acetylated by N-acetyltransferase. Exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11.
Sulfamethazine is an antimicrobial sulfur drug that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfamethazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid1. It induces CYP3A4 expression and is acetylated by N-acetyltransferase. It exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11. Sulfamethazine is bacteriostatic.
Application
Sulfamethazine is an antibiotic used to treat bronchitis, prostatitis and urinary tract infections1. It is used in disposition and depletion kinetic studies2,3. It is used to develop detection techniques for quantification in fluids such as cows’ milk, honey and swine urine4.

Sigma Aldrich - 46802

Biochem/physiol Actions
An antimicrobial sulfur drug. Induces CYP3A4 expression and acetylated by N-acetyltransferase. Exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699074

Antibacterial.

REFERENCES

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