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S6256 Sigma-Aldrich

Sulfamethazine

99.0-101.0% (on dried basis)

Synonym: 4,6-Dimethylsulfadiazine, 4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide, Sulfadimethyldiazine, Sulfadimidine

  • CAS Number 57-68-1

  • Empirical Formula (Hill Notation) C12H14N4O2S

  • Molecular Weight 278.33

  •  Beilstein/REAXYS Number 261304

  •  EC Number 200-346-4

  •  MDL number MFCD00006066

  •  PubChem Substance ID 24899686

  •  NACRES NA.85

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Mechanism of Action,
Quality Level   200
assay   99.0-101.0% (on dried basis)
form   powder or crystals
color   white to off-white
Mode of action   DNA synthesis | interferes
  enzyme | inhibits
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
storage temp.   2-8°C
SMILES string   Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1
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)
InChI key   ASWVTGNCAZCNNR-UHFFFAOYSA-N

Description

General description

Chemical structure: sulfonamide

Application

Sulfamethazine is an antibiotic used to treat bronchitis, prostatitis and urinary tract infections. It is used in disposition and depletion kinetic studies. It is used to develop detection techniques for quantification in fluids such as cows’ milk, honey and swine urine.

Biochem/physiol Actions

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 acid. 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.

An antimicrobial sulfur drug. Induces CYP3A4 expression and acetylated by N-acetyltransferase. Exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11.

Packaging

25G,100G

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
WO9275000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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