Sulfacetamide
Title: Sulfacetamide
CAS Registry Number: 144-80-9
CAS Name: N-[(4-Aminophenyl)sulfonyl]acetamide
Additional Names: N-sulfanilylacetamide; N1-acetylsulfanilamide; p-aminobenzenesulfonoacetamide
Molecular Formula: C8H10N2O3S
Molecular Weight: 214.24
Percent Composition: C 44.85%, H 4.70%, N 13.08%, O 22.40%, S 14.97%
Literature References: Incorrectly called sulfacetimide. Prepn: M. L. Crossley et al., J. Am. Chem. Soc. 61, 2950 (1939); M. Dohrn, P. Diedrich, Muench. Med. Wochenschr. 85, 2017 (1938); eidem, US 2411495 (1946 to Schering). Toxicity: R. S. Fisher, H. B. Haag, J. Urol. 47, 183 (1942). Antimicrobial activity: R. D. Houlsby et al., J. Pharm. Sci. 72, 1401 (1983). GC determn in animal tissues: A. E. Mooser, H. Koch, J. AOAC Int. 76, 976 (1993). Clinical trial in conjunctivitis: J. A. Lohr et al., Pediatr. Infect. Dis. J. 7, 626 (1988); in acne: D. L. Breneman, M. C. Ariano, Int. J. Dermatol. 32, 365 (1993). Comprehensive description: I. Ahmad et al., Anal. Profiles Drug Subs. Excip. 23, 471-509 (1994).
Properties: White or yellowish white prisms, mp 182-184°. Acidic, slightly saline taste. uv max (water, 0.1M HCl, 0.1M HCl, 0.1M NaOH): 258, 217, 270, 256 (am 17700, 18900, 8900, 17300). Soluble in 150 parts water at 20°, in 15 parts alcohol, in 7 parts acetone. Sol in mineral acids and soln of alkali hydroxides and carbonates. Slightly sol in ether; very slightly sol in chloroform. An aq soln is acid to litmus. LD50 orally in dogs: 8000 mg/kg (Fisher).
Melting point: mp 182-184°
Absorption maximum: uv max (water, 0.1M HCl, 0.1M HCl, 0.1M NaOH): 258, 217, 270, 256 (am 17700, 18900, 8900, 17300)
Toxicity data: LD50 orally in dogs: 8000 mg/kg (Fisher)
 
Derivative Type: Sodium salt
CAS Registry Number: 127-56-0; 6209-17-2 (monohydrate)
Additional Names: Soluble sulfacetamide
Trademarks: Ak-Sulf (Akorn); Albucid (Ankerpharm); Antébor (Biologiques); Beocid-Puroptal (Metochem); Bleph-10 (Allergan); Cetamide (Alcon); Prontamid (SIT); Sebizon (Schering); Sodium Sulamyd (Schering); Sulf-10 (Novartis); Sulten-10 (Bausch & Lomb)
Molecular Formula: C8H9N2NaO3S
Molecular Weight: 236.22
Percent Composition: C 40.68%, H 3.84%, N 11.86%, Na 9.73%, O 20.32%, S 13.57%
Properties: Minute prisms from dil alcohol, mp 257°. Occurs as the monohydrate; white, odorless, crystalline powder with slightly bitter taste. uv max (pH 7.0 phosphate buffer, 0.1M HCl, aq. acid, 0.1M NaOH, aq alkali): 255, 271, 271, 256, 256 (A1cm1% 660-720, 207, 260, 626, 750). Sol in 1.5 parts water. Slightly sol in 96% ethanol; sparingly sol in acetone. Practically insol in ether and chloroform. pKa1 (amino group): 1.8; pKa2 (sulfonamide group at 25°): 5.4.
Melting point: mp 257°
pKa: pKa1 (amino group): 1.8; pKa2 (sulfonamide group at 25°): 5.4
Absorption maximum: uv max (pH 7.0 phosphate buffer, 0.1M HCl, aq. acid, 0.1M NaOH, aq alkali): 255, 271, 271, 256, 256 (A1cm1% 660-720, 207, 260, 626, 750)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides.

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