Compound Selection

Formula: C11H13N3O3S

MW: 267.31

CAS: 127-69-5


IUPAC: [(4-aminophenyl)sulfonyl](3,4-dimethylisoxazol-5-yl)amine

Smiles: c1(ccc(cc1)S(=O)(=O)Nc1c(c(no1)C)C)N




N+O: 6

Chiral Centers: 0

LogP: 1.18

LogS: -3.26


Monograph Number: 0009041

Title: Sulfisoxazole

CAS Registry Number: 127-69-5

CAS Name: 4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

Additional Names: N1-(3,4-dimethyl-5-isoxazolyl)sulfanilamide; 3,4-dimethyl-5-sulfanilamidoisoxazole; 5-(4-aminophenylsulfonamido)-3,4-dimethylisoxazole; 5-(p-aminobenzenesulfonamido)-3,4-dimethylisooxazole; sulfafurazole; sulphafurazole

Trademarks: Gantrisin (Roche); Sosol (McKesson); Soxisol (Fort Dodge); Soxomide (Upjohn); Sulfalar (Parke-Davis); Sulfazin (Shionogi); Sulfoxol (Orion)

Molecular Formula: C11H13N3O3S

Molecular Weight: 267.30.

Percent Composition: C 49.43%, H 4.90%, N 15.72%, O 17.96%, S 12.00%

Literature References: Prepn: H. M. Wuest, M. Hoffer, US 2430094 (1947 to Hoffmann-La Roche). Toxicity study: Seki et al., Arzneim.-Forsch. 15, 1441 (1965). Comprehensive description: B. C. Rudy, B. Z. Senkowski, Anal. Profiles Drug Subs. 2, 487-506 (1973). HPLC determn in biological fluids: D. Jung, S. Oie, Clin. Chem. 26, 51 (1980). Clinical trial in otitis media: P. A. M. Bernard et al., Pediatrics 88, 215 (1991).

Properties: White to slightly yellowish crystalline powder. Bitter taste. mp 194. pKa 5. Soly in water (25): 0.13 mg/ml. Sol in alcohol. LD50 orally in mice: 6800 mg/kg (Seki).

Melting point: mp 194

pKa: pKa 5

Toxicity data: LD50 orally in mice: 6800 mg/kg (Seki)

Derivative Type: Diethanolamine salt

CAS Registry Number: 4299-60-9

Additional Names: Sulfisoxazole diolamine

Trademarks: Suladrin (Alcon); Sulfium (Alcon)

Molecular Formula: C11H13N3O3S.C4H11NO2

Molecular Weight: 372.44.

Percent Composition: C 48.37%, H 6.50%, N 15.04%, O 21.48%, S 8.61%

Properties: White to off-white, odorless, crystalline powder. Sol in alcohol; freely sol in water. A 4% soln is about isotonic with tears.

Derivative Type: Acetyl sulfisoxazole

CAS Registry Number: 80-74-0

CAS Name: N-[(4-Aminophenyl)sulfonyl]-N-(3,4-dimethyl-5-isoxazolyl)acetamide

Additional Names: N1-monoacetyl sulfisoxazole

Molecular Formula: C13H15N3O4S

Molecular Weight: 309.34.

Percent Composition: C 50.47%, H 4.89%, N 13.58%, O 20.69%, S 10.37%

Literature References: Prepn: M. Hoffer, US 2721200 (1955 to Hoffmann-La Roche). Should not be confused with N4-acetyl sulfisoxazole which is a metabolite.

Properties: Tasteless crystals, mp 193-194. Soly (mg/ml): 0.07 in water; 4.93 in methanol; 5.7 in 95% ethanol; 0.94 in ether; 29.0 in chloroform.

Melting point: mp 193-194

Therap-Cat: Antibacterial.

Therap-Cat-Vet: Antibacterial.

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