SKU: S120

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Description

Sulfisoxazole is a bioactive small molecule and broad-spectrum sulfanilamide antibacterial agent with an oxazole substituent. It is an ETA selective endothelin receptor antagonist (ETAR antagonist). It is a synthetic analog of the natural compound para-aminobenzoic acid (PABA).

    CAS Number

    127-69-5

    Molecular Formula

    C11H13N3O3S

    Molecular Weight

    267.30

    Mechanism of Action

    Sulfisoxazole competes with PABA for the bacterial dihydropteroate synthase, thus preventing incorporation of PABA into dihydrofolic acid, the precursor to folic acid. Folic acid is a coenzyme in the synthesis of purines and pyrimidines, leading to reduced cell growth and cell death. Unlike bacteria (and fungi/ plants) that synthesize their own folic acid, mammals do not, and thus are unaffected by PABA inhibitors.

    Storage Conditions

    2-8C

    Tariff Code

    2935.90.7500

    Spectrum

    Broad-spectrum against a range of Gram-positive and Gram-negative bacteria including otitis media.

Applications

    Microbiology Applications

    Sulfisoxazole is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (Sensi-Disc, from BD) against Gram- positive and Gram-negative bacteria. Sulfisoxazole has IC50 of 0.6 uM for ETA receptor, and 22 uM for rETA receptor. Sulfisoxazole was used in a novel engineered E. coli 12-member reporter panel of bioluminescent reporter stains, constructed using a novel non-antibiotic selection system, to survey environmental residues. The selectivity marker was developed based on the requirement for tryptophan, and folic acid-free medium was employed (Melamed et al, 2012).

Specifications

    Form

    Solid

    Appearance

    Solid

    Source

    Synthetic

References

    References

    Chan MF(1994) Identification of a new class of ETA selective endothelin antagonists by pharmacophore directed screening. Biochem Biophys. Res. Commun. 201(1):228-234. PMID 8198578 Kuo C, Wang S and Grayston JT (1977) Antimicrobial activity of several antibiotics and a sulfonamide against Chlamydia trachomatis organisms in cell culture. Antimicrob. Agents. Chemother. 12(1):80-83 Antimicrobial Agents and Chemotherapy Jul 1977, 12 (1) 80-83; DOI: 10.1128/AAC.12.1.80 Melamed S et al (2012) A bacterial reporter panel for the detection and classification of antibiotic substances.Microb Biotechnol. 5(4):536-548

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