Chlortetracycline
Title: Chlortetracycline
CAS Registry Number: 57-62-5
CAS Name: [4S-(4a,4aa,5aa,6b,12aa)]-7-Chloro-4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
Additional Names: 7-chlorotetracycline
Trademarks: Acronize (Am. Cyanamid); Aureocina; Aureomycin (Lederle); Biomitsin; Centraureo (Central); Chrysomykine; Orospray (V oquinol)
Molecular Formula: C22H23ClN2O8
Molecular Weight: 478.88
Percent Composition: C 55.18%, H 4.84%, Cl 7.40%, N 5.85%, O 26.73%
Literature References: Antibiotic substance isolated from the substrate of Streptomyces aureofaciens: Duggan, Ann. N.Y. Acad. Sci. 51, 177 (1948); US 2482055 (1949 to Am. Cyanamid); Broschard et al., Science 109, 199 (1949). Structure: Stephens et al., J. Am. Chem. Soc. 74, 4976 (1952); 76, 3568 (1954). Crystal structure: Donohue et al., ibid. 85, 851 (1963). Absolute configuration: Dobrynin et al., Tetrahedron Lett. 1962, 901. Purification: Winterbottom et al., US 2899422 (1959 to Am. Cyanamid). Improved process: Miller et al.; Goodman, US 2987449; US 3050446 (1961, 1962 to Am. Cyanamid). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description: G. Schwartzman et al., Anal. Profiles Drug Subs. 8, 101-137 (1979).
Properties: Golden-yellow crystals, mp 168-169°. [a]D23 -275.0° (methanol). uv max (0.1N HCl): 230, 262.5, 367.5 nm; (0.1N NaOH): 255, 285, 345 nm. Soly in water: 0.5-0.6 mg/ml. Very sol in aq solns above pH 8.5. Freely sol in the Cellosolves, dioxane, and Carbitol. Slightly sol in methanol, ethanol, butanol, acetone, ethyl acetate, benzene. Practically insol in ether, petr ether.
Melting point: mp 168-169°
Optical Rotation: [a]D23 -275.0° (methanol)
Absorption maximum: uv max (0.1N HCl): 230, 262.5, 367.5 nm; (0.1N NaOH): 255, 285, 345 nm
 
Derivative Type: Crystal salt
Properties: White powder. Insol in water. Marketed as suspension preserved with methyl and propyl p-hydroxybenzoate; stable and fully active for at least one year at room temps.
 
Derivative Type: Hydrochloride
CAS Registry Number: 64-72-2
Trademarks: Aureociclina; Isphamycin
Molecular Formula: C22H23ClN2O8.HCl
Molecular Weight: 515.34
Percent Composition: C 51.27%, H 4.69%, Cl 13.76%, N 5.44%, O 24.84%
Properties: Bitter, yellow rhomboid crystals. Dec above 210°. [a]D23 -240°. Soly at about 28° (mg/ml): water 8.6; methanol 17.4; ethanol 1.7: Weiss et al., Antibiot. Chemother. 7, 374 (1957). Sol in solns of alkali hydroxides and carbonates. Practically insol in acetone, ether, chloroform, dioxane. pH of satd aq soln 2.8-2.9. LD50 orally in rats: 10300 mg/kg (Goldenthal).
Optical Rotation: [a]D23 -240°
Toxicity data: LD50 orally in rats: 10300 mg/kg (Goldenthal)
 
Therap-Cat: Antibacterial; antiamebic.
Therap-Cat-Vet: Antimicrobial.
Keywords: Antiamebic; Antibacterial (Antibiotics); Tetracyclines.

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