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Merck

S6256

Sulfamethazine

99.0-101.0% (on dried basis)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H14N4O2S
CAS Number:
57-68-1
Molecular Weight:
278.33
UNSPSC Code:
51284910
NACRES:
NA.85
PubChem Substance ID:
24899686
EC Number:
200-346-4
Beilstein/REAXYS Number:
261304
MDL number:
MFCD00006066

Product Name

Sulfamethazine, 99.0-101.0% (on dried basis)

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

SMILES string

Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1

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

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

2-8°C

Quality Level

200

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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

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 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.

General description

Chemical structure: sulfonamide

Other Notes

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

Packaging

25G,100G

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000430823
0000430823
0000410520
0000410520
0000401241

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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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