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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:
6733588
EC Number:
200-685-8
MDL number:
MFCD00006065
UNSPSC Code:
51283908
PubChem Substance ID:
24899802
NACRES:
NA.85
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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.

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[1]. Sulfadiazine has been used to control acute infections when studying murine models of reactivated toxoplasmosis[2].

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[1]. 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

Signal Word

Warning

Hazard Statements

H302,H361d,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000405084
0000370960
0000350214
0000336877
0000322550

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Sven Jechalke et al.
Applied and environmental microbiology, 79(5), 1704-1711 (2013-01-15)
Spreading manure containing antibiotics in agriculture is assumed to stimulate the dissemination of antibiotic resistance in soil bacterial populations. Plant roots influencing the soil environment and its microflora by exudation of growth substrates might considerably increase this effect. In this
Ildiko R Dunay et al.
Antimicrobial agents and chemotherapy, 53(10), 4450-4456 (2009-07-29)
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
Pascale Meneceur et al.
Antimicrobial agents and chemotherapy, 52(4), 1269-1277 (2008-01-24)
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
Romain Sonneville et al.
Neurology, 79(17), 1762-1766 (2012-10-12)
Cerebral toxoplasmosis remains a common neurologic complication in patients with AIDS. In this study, we aimed to characterize the prognosis of patients with HIV infection with severe forms of cerebral toxoplasmosis and to investigate the effects of adjunctive steroids on
Tamim M Niazi et al.
International journal of radiation oncology, biology, physics, 84(3), e305-e310 (2012-06-02)
For patients with anal canal and advanced rectal cancer, chemoradiation therapy is a curative modality or an important adjunct to surgery. Nearly all patients treated with chemoradiation experience some degree of radiation-induced dermatitis (RID). Prevention and effective treatment of RID
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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