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S0127

Sigma-Aldrich

Sulfathiazole sodium salt

≥99%

Synonym(s):

4-Amino-N-(2-thiazolyl)benzenesulfonamide sodium salt

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About This Item

Empirical Formula (Hill Notation):
C9H8N3NaO2S2
CAS Number:
144-74-1
Molecular Weight:
277.30
Beilstein:
3802297
EC Number:
205-638-5
MDL number:
MFCD00072133
UNSPSC Code:
51101500
PubChem Substance ID:
24899426
NACRES:
NA.85

biological source

synthetic (Organic)

Assay

≥99%

form

powder

color

white to off-white

solubility

H2O: soluble 50 mg/mL

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)N([Na])c2nccs2

InChI

1S/C9H8N3O2S2.Na/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9;/h1-6H,10H2;/q-1;+1

InChI key

GWIJGCIVKLITQK-UHFFFAOYSA-N

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General description

Chemical structure: sulfonamide

Application

Sulfathiazole is a short-acting sulfa drug. It was a common oral and topical antibiotic until less toxic alternatives were discovered. It is no longer used in humans. Sulfathiazole is added to the diet of laboratory animals to inhibit folate formation by gut bacteria. This ensures that the animal′s only source of available folate is from their diet.

Biochem/physiol Actions

Sulfathiazole is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfathiazole 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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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Aron M Troen et al.
The Journal of nutrition, 138(12), 2502-2509 (2008-11-22)
Poor folate status is associated with cognitive decline and dementia in older adults. Although impaired brain methylation activity and homocysteine toxicity are widely thought to account for this association, how folate deficiency impairs cognition is uncertain. To better define the
T Lotti et al.
Water science and technology : a journal of the International Association on Water Pollution Research, 66(7), 1519-1526 (2012-08-07)
The feasibility of anaerobic ammonium oxidation (anammox) process to treat wastewaters containing antibiotics and heavy metals (such as the liquid fraction of the anaerobically digested swine manure) was studied in this work. The specific anammox activity (SAA) was evaluated by
Mi-Kyung Yun et al.
Science (New York, N.Y.), 335(6072), 1110-1114 (2012-03-03)
The sulfonamide antibiotics inhibit dihydropteroate synthase (DHPS), a key enzyme in the folate pathway of bacteria and primitive eukaryotes. However, resistance mutations have severely compromised the usefulness of these drugs. We report structural, computational, and mutagenesis studies on the catalytic
Yun Hu et al.
Journal of pharmaceutical and biomedical analysis, 53(3), 412-420 (2010-07-08)
The simultaneous quantitative analysis of sulfathiazole polymorphs (forms I, III and V) in ternary mixtures by attenuated total reflectance-infrared (ATR-IR), near-infrared (NIR) and Raman spectroscopy combined with multivariate analysis is reported. To reduce the effect of systematic variations, four different
Yun Hu et al.
Journal of pharmaceutical sciences, 102(1), 93-103 (2012-10-11)
The formation and physical stability of amorphous sulfathiazole obtained from polymorphic forms I and III by cryomilling was investigated by X-ray powder diffraction (XRPD) and near-infrared (NIR) spectroscopy. Principal component analysis was applied to the NIR data to monitor the
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