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S8626

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

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

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

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35033BP3121625009
Sulfadiazine 99.0-101.0%

Sigma-Aldrich

S8626

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Sulfadiazine VETRANAL®, analytical standard

Supelco

35033

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Sulfadiazine British Pharmacopoeia (BP) Reference Standard

BP312

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Sulfadiazine United States Pharmacopeia (USP) Reference Standard

USP

1625009

Sulfadiazine

antibiotic activity spectrum

Gram-negative bacteria, mycoplasma, Gram-positive bacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycoplasma

antibiotic activity spectrum

-

antibiotic activity spectrum

-

mode of action

enzyme | inhibits, DNA synthesis | interferes

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

mode of action

-

form

powder or crystals

form

-

form

solid

form

-

assay

99.0-101.0%

assay

-

assay

-

assay

-

solubility

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

solubility

-

solubility

-

solubility

-

mp

253 °C (dec.) (lit.)

mp

253 °C (dec.) (lit.)

mp

253 °C (dec.) (lit.)

mp

253 °C (dec.) (lit.)

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Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000546597
0000546597
0000504482
0000504482
0000486684

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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
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
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
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Questions

1–2 of 2 Questions  

  1. 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/418/501/product-dating-information-06-25-mk.pdf

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  2. 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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