8943. Sulfathiazole

Nomenclature

CAS number: 72-14-0
4-Amino-N-2-thiazolylbenzenesulfonamide; N1-2-thiazolylsulfanilamide; 2-sulfanilamidothiazole; 2-(sulfanilylamino)thiazole; 2-(p-aminobenzenesulfonamido)thiazole; norsulfazole; RP-2090; M & B 760; Thiazamide (May & Baker); Cibazol (Novartis); Enterobiocine (Rousselot); Duatok (Am. Cyanamid); Sulfamul (Frosst); Sulfavitina (CT); Sulzol (Yoshitomi).
C9H9N3O2S2; mol wt 255.32.
C 42.34%, H 3.55%, N 16.46%, O 12.53%, S 25.12%.

Description and references

Prepn: R. J. Fosbinder, L. A. Walter, J. Am. Chem. Soc. 61, 2032 (1939); W. A. Lott, F. H. Bergeim, ibid. 3593; G. Newbery, P. Viaud, GB 517272; G. Newbery, US 2362087 (1940, 1944 both to May & Baker). Antibacterial activity in vivo: O. W. Barlow, E. Homburger, Proc. Soc. Exp. Biol. Med. 42, 792 (1939). Toxicology: H. B. van Dyke et al., ibid. 410; P. H. Long et al., ibid. 43, 328 (1940). Review of early literature: ACS Monograph Series no. 106, entitled “Sulfonamides and Allied Compounds,” E. H. Northey, Ed. (Reinhold, New York, 1948) 660 pp. HPLC determn in milk: V. K. Agarwal, J. Liq. Chromatogr. 16, 3793 (1993). Oral bioavailability in ruminants: K. Weijkamp et al., Vet. Q. 16, 33 (1994). Comprehensive description: V. K. Kapoor, Anal. Profiles Drug Subs. Excip. 22, 389-430 (1993).

Chemical structure

Properties

mp 202-202.5°. pKa 7.2. Soly at 26° (mg/100 ml): water 60 (pH 6.03); alcohol 525. Sol in acetone, dil mineral acids, KOH and NaOH solns, ammonia water. Very slightly sol in water; sparingly sol in ethanol. Practically insol in chloroform, ether.

Derivative

Sodium salt sesquihydrate.

Nomenclature

Soluble sulfathiazole.
C9H8N3NaO2S2.1H2O; mol wt 286.31.
C 37.75%, H 3.17%, N 14.68%, Na 8.03%, O 13.97%, S 22.40%.

Properties

Crystals or white powder or granules. Also occurs as the monohydrate and pentahydrate. One gram dissolves in ≈2.5 ml water, in ≈15 ml alc. pH of 1% aq soln 9.35; of 10% soln 10.2. LD50 s.c. in mice: 1.45 g/kg (van Dyke); also reported as 1.95 g/kg (Long).

Derivative

Polymer with formaldehyde.

Nomenclature

CAS number: 12041-72-4
Formosulfathiazole; formaldehyde-sulfathiazole; Forbina (Novartis).

Description and references

(C9H9N3O2S2.CH2O)x. Contains ≈11% formaldehyde. Prepn: J. Druey, A. Becker, Helv. Chim. Acta 31, 2184 (1948). Intrauterine use in cows: D. P. Dobson, D. E. Noakes, Vet. Rec. 127, 128 (1990).

Properties

Amorphous powder. Practically insol in water.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides