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S8626

Sigma-Aldrich

Sulfadiazine

99.0-101.0%

Synonym(s):

4-Amino-N-(2-pyrimidinyl)benzenesulfonamide, N1-(Pyrimidin-2-yl)sulfanilamide

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About This Item

Empirical Formula (Hill Notation):
C10H10N4O2S
CAS Number:
68-35-9
Molecular Weight:
250.28
Beilstein/REAXYS Number:
6733588
EC Number:
200-685-8
MDL number:
MFCD00006065
UNSPSC Code:
51101500
PubChem Substance ID:
24899802
NACRES:
NA.85

description

Solubility - Practically insoluble in water, slightly soluble in acetone, very slightly soluble in ethanol (96 per cent). It dissolves in solutions of alkali hydroxides and in dilute mineral acids.

Quality Level

200

assay

99.0-101.0%

form

powder or crystals

color

white to faint yellow, faint pink

mp

253 °C (dec.) (lit.)

solubility

96% ethanol: very slightly soluble
acetone: slightly soluble
water: practically insoluble

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma

mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

Nc1ccc(cc1)S(=O)(=O)Nc2ncccn2

InChI

1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

InChI key

SEEPANYCNGTZFQ-UHFFFAOYSA-N

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General description

Chemical structure: sulfonamide

Application

Sulfadiazine is a short-acting sulfonamide that is commonly used with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome. It is also used to treat newborns with congenital infections. Sulfadiazine has been used to control acute infections when studying murine models of reactivated toxoplasmosis.

Biochem/physiol Actions

Sulfadiazine is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Storage class (TRGS 510): Non Combustible Solids

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sulfameter

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Sulfameter

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Immunocompromised patients are at risk of developing toxoplasmosis, and although chemotherapy is available, standard treatments are often complicated by severe side effects. Artemisinin is a new highly potent antimalarial drug that has activity against Toxoplasma gondii in vitro. However, artemisinin
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Sulfadiazine, pyrimethamine, and atovaquone are widely used for the treatment of severe toxoplasmosis. Their in vitro activities have been almost exclusively demonstrated on laboratory strains belonging to genotype I. We determined the in vitro activities of these drugs against 17
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