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Merck

S5637

Sulfamethazine sodium salt

≥98%

Synonym(s):

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

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About This Item

Linear Formula:
C12H13N4O2SNa
CAS Number:
1981-58-4
Molecular Weight:
300.31
NACRES:
NA.85
PubChem Substance ID:
24899666
UNSPSC Code:
51284910
EC Number:
217-840-0
MDL number:
MFCD00068333

Product Name

Sulfamethazine sodium salt, ≥98%

InChI key

WIVZAHIZHZEEOX-UHFFFAOYSA-N

InChI

1S/C12H14N4O2S.Na.H/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);;

SMILES string

[Na].Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1

assay

≥98%

form

powder

storage condition

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

color

white to off-white

solubility

H2O: soluble 50 mg/mL

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

Related Categories

Application

Sulfamethazine is an antibiotic used to clinically 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.

General description

Chemical structure: sulfonamide

Other Notes

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

Packaging

25G,100G

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000438492
0000438492
0000307900
0000307900
0000258282

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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
Bożena Czubat et al.
Frontiers in microbiology, 11, 2008-2008 (2020-09-26)
MSMEG_4305 is a two-domain protein of Mycolicibacterium smegmatis (Mycobacterium smegmatis) (Mycolicibacterium smegmatis). The N-terminal domain of MSMEG_4305 encodes an RNase H type I. The C-terminal domain is a presumed CobC, predicted to be involved in the aerobic synthesis of vitamin
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
Craig Knox et al.
Nucleic acids research, 39(Database issue), D1035-D1041 (2010-11-10)
DrugBank (http://www.drugbank.ca) is a richly annotated database of drug and drug target information. It contains extensive data on the nomenclature, ontology, chemistry, structure, function, action, pharmacology, pharmacokinetics, metabolism and pharmaceutical properties of both small molecule and large molecule (biotech) drugs.
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