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.
Chloranil Chloranilic Acid Chlorazanil Chlorbenside Chlorbenzoxamine

Chloramphenicol
Chloramphenicol-2D-skeletal.svg
Chloramphenicol-3D-vdW.png
Systematic (IUPAC) name
2,2-dichloro-N-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a608008
Licence data US FDA:link
Pregnancy cat. A (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Topical (ocular), oral, IV, IM
Pharmacokinetic data
Bioavailability 75–90%
Protein binding 60%
Metabolism Hepatic
Half-life 1.6-3.3 hours
Excretion Renal (5-15%), faeces (4%)
Identifiers
CAS number 56-75-7 YesY
ATC code D06AX02 D10AF03 G01AA05 J01BA01 S01AA01 S02AA01 S03AA08 QJ51BA01
PubChem CID 298
DrugBank DB00446
ChemSpider 5744 YesY
UNII 66974FR9Q1 YesY
KEGG D00104 YesY
ChEBI CHEBI:17698 YesY
ChEMBL CHEMBL130 YesY
Chemical data
Formula C11H12Cl2N2O5 
Mol. mass 323.1320 g/mol
 YesY (what is this?)  (verify)

Chloramphenicol (INN) is a bacteriostatic antimicrobial that became available in 1949. It is considered a prototypical broad-spectrum antibiotic, alongside the tetracyclines, and as it is both cheap and easy to manufacture it is frequently an antibiotic of choice in the Developing World.

Chloramphenicol, also known as chlornitromycin, is effective against a wide variety of Gram-positive and Gram-negative bacteria, including most anaerobic organisms. Due to resistance and safety concerns, it is no longer a first-line agent for any infection in developed nations, with the notable exception of topical treatment of bacterial conjunctivitis. Nevertheless, the global problem of advancing bacterial resistance to newer drugs has led to renewed interest in its use.[1] In low-income countries, chloramphenicol is still widely used because it is inexpensive and readily available.

The most serious adverse effect associated with chloramphenicol treatment is bone marrow toxicity, which may occur in two distinct forms: bone marrow suppression, which is a direct toxic effect of the drug and is usually reversible, and aplastic anemia, which is idiosyncratic (rare, unpredictable, and unrelated to dose) and generally fatal.[2]

Pure chloramphenicol