GLPBio

Sulfamethoxazole

Catalog No.: GC11874Purity:>99.50%Synonyms: NSC 147832, Ro 4-2130
COASDSData Sheet
Sulfamethoxazole is a bacteriostatic sulfonamide antibiotic.

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Sulfamethoxazole
Cas No.: 723-46-6
10mM (in 1mL DMSO)In Stock
$35.00
1
100mgIn Stock
$19.00
1
500mgIn Stock
$51.00
1
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Description

Sulfamethoxazole is a bacteriostatic sulfonamide antibiotic [1]. Sulfamethoxazole competitively inhibits bacterial dihydropteroate synthase (DHPS), blocking folate synthesis and thereby interfering with DNA and protein synthesis [2-3]. Sulfamethoxazole is widely used to treat urinary tract infections, respiratory tract infections, and gastrointestinal infections [4].

In E. coli, after Sulfamethoxazole (1.6mg/mL; 24h) treatment, the activity of bacterial was significantly inhibited [5]. In mouse pancreatic β cells, Sulfamethoxazole (0.1-10mM; 3h) treatment inhibits the channel current of KATP and the inhibition is dose-dependent [6].

In Toxoplasma gondii infected mouse model, Sulfamethoxazole (300mg/kg; po; 24d) significantly decreased mortality among the infected WT C57BL/6 and GKO mice [7]. In danio rerio, Sulfamethoxazole (250ppm; embryo culture;5d) induces brain capillary toxicity by upregulating VEGF and chemokine signaling [8].

References:
[1]. Rudy B C, Senkowski B Z. Sulfamethoxazole[M]//Analytical profiles of drug substances. Academic Press, 1973, 2: 467-486.
[2]. Fernández-Villa D, Aguilar M R, Rojo L. Folic acid antagonists: antimicrobial and immunomodulating mechanisms and applications[J]. International journal of molecular sciences, 2019, 20(20): 4996.
[3]. Cheong M S, Seo K H, Chohra H, et al. Influence of sulfonamide contamination derived from veterinary antibiotics on plant growth and development[J]. Antibiotics, 2020, 9(8): 456.
[4]. Petri W A. Sulfonamides, trimethoprim, sulfamethoxazole, quinolones, and agents for urinary tract infections[J]. Goodman & Gilman’s the pharmacological basis of therapeutics. New York (NY): McGraw Hill, 2006: 1111-1125.
[5]. Park H B, Wei Z, Oh J, et al. Sulfamethoxazole drug stress upregulates antioxidant immunomodulatory metabolites in Escherichia coli[J]. Nature microbiology, 2020, 5(11): 1319-1329.
[6]. Ogata H, Kitamura S, Fujiwara M, et al. Dose dependent effect of sulfamethoxazole on inhibiting KATP channel of mouse pancreatic β cell[J]. Dose-Response, 2023, 21(3): 15593258231203611.
[7]. Norose K, Aosai F, Mun H S, et al. Effects of sulfamethoxazole on murine ocular toxoplasmosis in interferon-γ knockout mice[J]. Investigative ophthalmology & visual science, 2006, 47(1): 265-271.
[8]. Xu Y, Luo L, Chen J. Sulfamethoxazole induces brain capillaries toxicity in zebrafish by up-regulation of VEGF and chemokine signalling[J]. Ecotoxicology and Environmental Safety, 2022, 238: 113620.

Protocol

Antibacterial experiments [1]:

Bacterial

E. coli

Preparation Method

E. coli strains were grown on LB agar plates [1% tryptone (w/v), 0.5% yeast extract (w/v), 1% sodium chloride (w/v), and 1.5% agar (w/v)] at 37℃ for 18h. Three well-defined colonies from each of the strains were inoculated into 5mL of LB broth and incubated at 37℃ with agitation (250rpm). Overnight E. coli cultures (5μL) were seeded into 5mL LB broth and were further grown for 18h. Sulfamethoxazole, when needed, was prepared in fresh LB medium with a highest concentration of 1.6mg/mL, which was then serially diluted. The 5mL of Sulfamethoxazole-containing medium was dispensed into 14mL sterile culture tubes, and 5μL of E. coli culture was inoculated and grown at 37℃ for 24h at 250rpm. The optical density (OD600) of cultures was measured, and growth curves were generated to determine sub-inhibitory levels of Sulfamethoxazole against E. coli.

Reaction Conditions

1.6mg/mL; 24h

Applications

After Sulfamethoxazole treatment, the activity of E. coli was significantly inhibited.
Animal experiment [2]:

Animal models

Toxoplasma gondii infected mouse model

Preparation Method

Wild-type (WT) C57BL/6 and WT BALB/c mice and interferon-γ knockout (GKO) mice were infected orally with Toxoplasma gondii of the Fukaya strain. Mice were classified into groups. The first group (G1) remained untreated, the second group (G2) had a short Sulfamethoxazole treatment period, and the third group (G3) received treatment continuously. WT and GKO mice were divided into G1 and G3, and G1, G2, and G3, respectively. T. gondii burdens were evaluated by QC-PCR assay. The effect on stage distribution was analyzed by reverse transcription-PCR.

Dosage form

300mg/kg; po; 24d

Applications

Sulfamethoxazole significantly decreased mortality among the infected WT C57BL/6 and GKO mice.

References:
[1]. Park H B, Wei Z, Oh J, et al. Sulfamethoxazole drug stress upregulates antioxidant immunomodulatory metabolites in Escherichia coli[J]. Nature microbiology, 2020, 5(11): 1319-1329.
[2]. Norose K, Aosai F, Mun H S, et al. Effects of sulfamethoxazole on murine ocular toxoplasmosis in interferon-? knockout mice[J]. Investigative ophthalmology & visual science, 2006, 47(1): 265-271.

Product Documents

Purity:>99.50%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
723-46-6
Synonyms
NSC 147832, Ro 4-2130
Chemical Name
4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
SMILES
CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
Molecular Formula
C10H11N3O3S
Molecular Weight
253.28
Solubility
≥ 7.75mg/mL in DMSO
Storage
Store at 2-8°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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