Chloramphenicol
Title: Chloramphenicol
CAS Registry Number: 56-75-7
CAS Name: 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide
Additional Names: D-threo-N-dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol; D(-)-threo-2-dichloroacetamido-1-p-nitrophenyl-1,3-propanediol; D-threo-N-(1,1¢-dihydroxy-1-p-nitrophenylisopropyl)dichloroacetamide
Trademarks: Aquamycetin (Winzer); Chlorocid (Egis); Chloromycetin (Warner-Lambert); Chloroptic (Allergan); Fenicol (Alcon); Pantovernil (BMS); Paraxin (Roche); Quemicetina (Pharmacia); Sintomicetina (Lepetit); Tifomycine (Aventis); Viceton (Bimeda)
Molecular Formula: C11H12Cl2N2O5
Molecular Weight: 323.13
Percent Composition: C 40.89%, H 3.74%, Cl 21.94%, N 8.67%, O 24.76%
Literature References: Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae: Bartz, J. Biol. Chem. 172, 445 (1948); Gottlieb et al., J. Bacteriol. 55, 409 (1948); Ehrlich et al., ibid. 56, 467 (1948). Isoln from the moon snail, Lunatia heros: C. A. Price et al., J. Antibiot. 34, 118 (1981). Structure: Rebstock et al., J. Am. Chem. Soc. 71, 2458 (1949). Synthesis: Controulis et al., ibid. 2463; Long, Troutman, ibid. 2469, 2473. See also US 2483871; US 2483884; US 2483892. Alternate synthesis: Ehrhart et al., Ber. 90, 2088 (1957); GB 795131; GB 796901 C.A. 53, 2161 (1959) (both to Chinoin); US 2839577 (1958 to Chinoin). Review and evaluation of toxicity studies: IARC Monographs 10, 85-98 (1976). Review of pharmacology and clinical efficacy: I. Shalit, M. I. Marks, Drugs 28, 281-291 (1984). Comprehensive description: D. Szulczewski, F. Eng, Anal. Profiles Drug Subs. 4, 47-90 (1975); A. A. Al-Badr, H. A. El-Obeid, ibid. 15, 701-760 (1986). Reviews: Hahn in Antibiotics vol. 1, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 308-330; Pestka, ibid. vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (1975) pp 370-395; O. Pongs, ibid. vol. 5, pt. 1, F. E. Hahn, Ed. (1979) pp 26-42.
Properties: Needles or elongated plates from water or ethylene dichloride. mp 150.5-151.5°. Sublimes in high vacuum. [a]D27 +18.6° (c = 4.86 in ethanol). [a]D25 -25.5° (ethyl acetate). uv max: 278 nm (E1%1cm 298). Soly (25°) in water: 2.5 mg/ml; in propylene glycol: 150.8 mg/ml. Very sol in methanol, ethanol, butanol, ethyl acetate, acetone. Fairly sol in ether. Insol in benzene, petr ether, vegetable oils. Soly in 50% acetamide soln about 5%. Additional soly data: Weiss et al., Antibiot. Chemother. 7, 374 (1957). Aq solns are neutral. Neutral and acid solns are stable on heating.
Melting point: mp 150.5-151.5°
Optical Rotation: [a]D27 +18.6° (c = 4.86 in ethanol); [a]D25 -25.5° (ethyl acetate)
Absorption maximum: uv max: 278 nm (E1%1cm 298)
 
Derivative Type: Monosuccinate sodium salt
CAS Registry Number: 982-57-0
Trademarks: Globenicol (Yamanouchi); Kemicetine (Pharmacia)
Molecular Formula: C15H15Cl2N2NaO8
Molecular Weight: 445.18
Percent Composition: C 40.47%, H 3.40%, Cl 15.93%, N 6.29%, Na 5.16%, O 28.75%
Properties: Freely sol in water (about 50% w/w).
 
Derivative Type: Palmitate
CAS Registry Number: 530-43-8
Trademarks: Chloropal (Graeub)
Literature References: Prepn: Edgerton, US 2662906 (1953 to Parke, Davis). Structure: Edgerton et al., J. Am. Chem. Soc. 77, 27 (1955). Description: Glazko et al., Antibiot. Chemother. 2, 234 (1952). Soly data: Weiss et al., ibid. 7, 374 (1957).
Properties: Crystals from benzene, mp 90°. Practically tasteless. [a]D26 +24.6° (c = 5 in ethanol). uv max (ethanol): 271 nm (E1%1cm 179). Very slightly sol in water (1.05 mg/ml at 28°); petr ether (0.225 mg/ml). Freely sol in methanol, ethanol, chloroform, ether, benzene.
Melting point: mp 90°
Optical Rotation: [a]D26 +24.6° (c = 5 in ethanol)
Absorption maximum: uv max (ethanol): 271 nm (E1%1cm 179)
 
Derivative Type: Monosuccinate arginine salt
CAS Registry Number: 34327-18-9
Additional Names: Chloramphenicol arginine succinate
Molecular Formula: C21H30Cl2N6O10
Molecular Weight: 597.40
Percent Composition: C 42.22%, H 5.06%, Cl 11.87%, N 14.07%, O 26.78%
Properties: mp 135-145° (dec). See Jpn. Med. Gaz. 7(10), 15 (1970).
Melting point: mp 135-145° (dec)
 
Derivative Type: Pantothenate calcium complex (4:1)
CAS Registry Number: 31342-36-6
Additional Names: Chloramphenicol pantothenate
Molecular Formula: C62H80CaCl8N10O30
Molecular Weight: 1769.05
Percent Composition: C 42.09%, H 4.56%, Ca 2.27%, Cl 16.03%, N 7.92%, O 27.13%
Literature References: Prepn: I. Villax, GB 866787; GB 866788; GB 866789 (all 1961); I. Villax, US 3078300 (1963).
 
CAUTION: Chloramphenicol is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-48.
Therap-Cat: Antibacterial; antirickettsial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Amphenicols; Antirickettsial.

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