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46802

Sulfamethazine

VETRANAL®, analytical standard

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:
41116107
NACRES:
NA.24
PubChem Substance ID:
329757245
EC Number:
200-346-4
Beilstein/REAXYS Number:
261304
MDL number:
MFCD00006066
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grade

analytical standard

Quality Level

200

agency

EPA 1694

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

application(s)

clinical testing

format

neat

mode of action

DNA synthesis | interferes, enzyme | inhibits

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

General description

Chemical structure: sulfonamide

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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 registered trademark of Merck KGaA, Darmstadt, Germany

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Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315

Hazard Classifications

Skin Irrit. 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Marina Islas-Espinoza et al.
Microbial ecology, 64(1), 140-151 (2012-01-31)
Persistence or degradation of synthetic antibiotics in soil is crucial in assessing their environmental risks. Microbial catabolic activity in a sandy loamy soil with pig manure using 12C- and 14C-labelled sulfamethazine (SMZ) respirometry showed that SMZ was not readily degradable.
Marc Teixidó et al.
Environmental science & technology, 45(23), 10020-10027 (2011-10-27)
Adsorption of ionizable compounds by black carbon is poorly characterized. Adsorption of the veterinary antibiotic sulfamethazine (SMT; a.k.a., sulfadimidine; pK(a1) = 2.28, pK(a2) = 7.42) on a charcoal was determined as a function of concentration, pH, inorganic ions, and organic
Juan Gao et al.
Environmental science & technology, 46(5), 2642-2651 (2012-01-17)
The transformation of the sulfonamide antimicrobial sulfamethazine (SMZ) by a synthetic analogue of the birnessite-family mineral vernadite (δ-MnO(2)) was studied. The observed pseudo-first-order reaction constants (k(obs)) decreased as the pH increased from 4.0 to 5.6, consistent with the decline in
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