S6377

Sigma-Aldrich

Sulfisoxazole

≥99.0%

Synonym(s):
N1-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide, 4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide, Sulfafurazole
Empirical Formula (Hill Notation):
C11H13N3O3S
CAS Number:
Molecular Weight:
267.30
Beilstein/REAXYS Number:
6737262
EC Number:
MDL number:
PubChem Substance ID:

assay

≥99.0%

solubility

acetone: complete 50 mg/ml
10% HCl: complete 33 mg/mL, clear, colorless to faintly yellow
alcohol: slightly soluble
chloroform: insoluble

originator

Roche

storage temp.

2-8°C

SMILES string

Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C

InChI

1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3

InChI key

NHUHCSRWZMLRLA-UHFFFAOYSA-N

Gene Information

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Application

Sulfisoxazole was one of the antibiotics tested on bacterial reporter panel that gave information on pollution load on the environment.11

Biochem/physiol Actions

Sulfisoxazole, a sulfonamide, is an antibacterial agent that acts by inhibiting the folic acid metabolism.1 It is also a non-selective endothelin antagonist. It is effective in the treatment of recurrent acute otitis media and also in rendering protection to retina against ischemic-like insults.2,3

Features and Benefits

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Certificate of Analysis

Certificate of Origin

Sahar Melamed et al.
Microbial biotechnology, 5(4), 536-548 (2012-03-06)
The ever-growing use of pharmaceutical compounds, including antibacterial substances, poses a substantial pollution load on the environment. Such compounds can compromise water quality, contaminate soils, livestock and crops, enhance resistance of microorganisms to antibiotic substances, and hamper human health. We...
I Varsano et al.
American journal of diseases of children (1960), 139(6), 632-635 (1985-06-01)
The efficacy of sulfisoxazole prophylaxis was evaluated in 32 otitis-prone children in a double-blind cross-over clinical trial. During the sulfisoxazole therapy, seven patients (22%) had nine episodes of acute otitis media (AOM) while 20 patients (63%) receiving placebo had 36...
Melina Mondelli et al.
Journal of inorganic biochemistry, 102(2), 285-292 (2007-11-03)
The synthesis, structural characterization, voltammetric experiments and antibacterial activity of [Ni(sulfisoxazole)(2)(H(2)O)(4)].2H(2)O and [Ni(sulfapyridine)(2)] were studied and compared with similar previously reported copper complexes. [Ni(sulfisoxazole)(2)(H(2)O)(4)].2H(2)O crystallized in a monoclinic system, space group C2/c where the nickel ion was in a slightly...
Petri Koivunen et al.
BMJ (Clinical research ed.), 328(7438), 487-487 (2004-02-11)
To evaluate the efficacy of adenoidectomy compared with long term chemoprophylaxis and placebo in the prevention of recurrent acute otitis media in children aged between 10 months and 2 years. Randomised, double blind, controlled trial. Oulu University Hospital, a tertiary...
Charles E Ahlfors et al.
Clinica chimica acta; international journal of clinical chemistry, 365(1-2), 78-85 (2005-09-20)
Measuring plasma unbound bilirubin concentration by the peroxidase test is useful in the management of jaundiced newborns. However, the commercially available peroxidase technology is manual, and the unbound bilirubin may be seriously underestimated at the 42-fold sample dilution and single...

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