8919. Sulfamethoxypyridazine

Nomenclature

CAS number: 80-35-3
4-Amino-N-(6-methoxy-3-pyridazinyl)benzenesulfonamide; N1-(6-methoxy-3-pyridazinyl)sulfanilamide; 6-methoxy-3-sulfanilamidopyridazine; 3-(p-aminobenzenesulfamido)-6-methoxypyridazine; CL-13494; RP-7522; Lederkyn (Wyeth); Midicel (Warner-Lambert); Midikel (Parke-Davis).
C11H12N4O3S; mol wt 280.30.
C 47.13%, H 4.32%, N 19.99%, O 17.12%, S 11.44%.

Description and references

Prepn: Clark, US 2712012 (1955 to Am. Cyanamid). Toxicity: Seki et al., Arzneim.-Forsch. 15, 1441 (1965). Toxicological, chemotherapeutic and pharmacokinetic studies: Bhni et al., Chemotherapy 14, 195-226 (1969).

Chemical structure

Properties

Bitter crystals from water, mp 182-183°. pKa 6.7. Soly in water at 37° (mg/100 ml): 110 at pH 5; 120 at pH 6; 147 at pH 6.5. Slightly sol in methanol, ethanol (about 1:200); more sol in acetone (1:50), in dimethylformamide (1 g/1 ml). Freely sol in aq solns of alkali hydroxides. LD50 orally in mice: 1750 mg/kg, (Seki).

Derivative

Sodium salt.

Nomenclature

CAS number: 2577-32-4
Davosin (Pharmacia); Sulfoxine LA (Univet).
C11H11N4NaO3S; mol wt 302.28.
C 43.71%, H 3.67%, N 18.53%, Na 7.61%, O 15.88%, S 10.61%.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides