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Merck
CN

S0127

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
UNSPSC Code:
51283955
NACRES:
NA.85
PubChem Substance ID:
24899426
EC Number:
205-638-5
Beilstein/REAXYS Number:
3802297
MDL number:
MFCD00072133

Key Documents

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InChI key

GWIJGCIVKLITQK-UHFFFAOYSA-N

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

SMILES string

Nc1ccc(cc1)S(=O)(=O)N([Na])c2nccs2

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

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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.

General description

Chemical structure: sulfonamide

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
067K0766
106K1933V
106K1933
116H0751
085F0409

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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
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
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
Jungkon Kim et al.
Chemosphere, 77(11), 1600-1608 (2009-10-20)
Phototoxicity of several environmental contaminants by UV light has been reported in many studies. Nevertheless, field observations suggest the presence of certain defense mechanisms that would protect aquatic organisms against phototoxic damages. The current study was conducted to understand the
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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