S6256

Sigma-Aldrich

Sulfamethazine

99.0-101.0% (on dried basis)

Synonym(s):
4,6-Dimethylsulfadiazine, 4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide, Sulfadimethyldiazine, Sulfadimidine
Empirical Formula (Hill Notation):
C12H14N4O2S
CAS Number:
Molecular Weight:
278.33
Beilstein/REAXYS Number:
261304
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85
Pricing and availability is not currently available.

Quality Level

assay

99.0-101.0% (on dried basis)

form

powder or crystals

storage condition

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

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

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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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

A D Mitchell et al.
Drug metabolism and disposition: the biological fate of chemicals, 14(2), 161-165 (1986-03-01)
Swine weighing 60-70 kg were orally administered 14C-sulfamethazine [4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzene[U-14C]sulfonamide] at 12-hr intervals for 7 days (165 mg/dose; 0.126-5.04 mCi/mmol). The animals were sacrificed at 8 hr or 2, 5, or 10 days after the last dose was given and tissues...
Tangbin Yang et al.
Hybridoma (2005), 29(5), 403-407 (2010-11-06)
A specific monoclonal antibody (MAb) against sulfamethazine was produced with hybridoma technology. This assay shows very high sensitivity with IC50 of 0.4 ng/mL and LOD of 0.05 ng/mL when it was run in 0.02 mol/L PBS (pH 7.5). This MAb has shown high...
C J Chapron et al.
Journal of clinical pharmacology, 16(7), 338-344 (1976-07-01)
The relationship between sulfamethazine disposition kinetics and acetylation phenotype was studied in man. Sulfamethazine pharmacokinetic parameters were determined after the administration of the drug as an oral suspension. When the half-life, acetylation rate constant, or per cent available dose excreted...
M Rérat et al.
Preventive veterinary medicine, 103(4), 265-273 (2011-09-29)
The present study was conducted to evaluate the efficacy of two prophylactic antibiotic treatments against bovine respiratory disease (BRD) in veal calves. In addition, the antibiotic susceptibilities of isolated Pasteurellaceae were tested. The calves were treated either on the day...
Vincent Curtin et al.
Molecular pharmaceutics, 10(1), 386-396 (2012-11-29)
The coprocessing of active pharmaceutical ingredient (API) with an excipient which has a high glass transition temperature (T(g)) is a recognized strategy to stabilize the amorphous form of a drug. This work investigates whether coprocessing a model API, sulfadimidine (SDM)...

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