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C0378 Sigma

Chloramphenicol

≥98% (HPLC)

Synonym: D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, Chloromycetin

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Properties

Related Categories A - K, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics A-F,
Quality Level   PREMIUM
assay   ≥98% (HPLC)
mp   148-150 °C(lit.)
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
  mycobacteria
  mycoplasma
Gene Information   human ... CYP1A2(1544)

Description

Application

Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It is often used for bacterial selection in molecular biology applications at 10-20 μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.

Biochem/physiol Actions

Mode of Action: Chloramphenicol inhibits bacterial protein synthesis by blocking the peptidyl transferase step by binding to the 50S ribosomal subunit and preventing attachment of aminoacyl tRNA to the ribosome. It also inhibits mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

Mode of Resistance: Use of chloramphenicol acetyltransferase will acetylate the product and inactivate it.

Antimicrobial Spectrum: This is a broad spectrum antibiotic against gram-positive and gram-negative bacteria, and is used mainly for ophthalmic and veterinary purposes.

Caution

Stock solutions should be stored at 2-8°C and are stable at 37°C for 5 days. Aqueous solutions are neutral and stable over a wide pH range, with 50% hydrolysis occurring after 290 days. Use of a borax buffered solution reduces this number to 14%. Solutions should be protected from light as photochemical decomposition results in a yellowing of the solution. Heating aqueous solutions at 115°C for 30 minutes results in a 10% loss of chloramphenicol.

Packaging

1 kg in poly bottle

5, 25, 100, 500 g in poly bottle

Preparation Note

A solution at 50 mg/mL in ethanol yields a clear, very faint, yellow solution. Degradation of chloramphenicol in aqueous solution is catalyzed by general acids and bases. This rate of degradation is independent of the ionic strength and pH.

Protocols & Applications

Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



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Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
45
Safety Statements (Europe) 
53-45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
AB6825000

Protocols & Articles

Articles

Fast Extraction and Low Level Detection of Chloramphenicol in Shrimp

QuEChERS Sample Preparation Using Z-Sep+ Sorbent and Analysis by Ascentis Express C18 LC-MS/MS
Emily Barrey, Olga Shimelis, Michael Halpenny, Jennifer Claus
Reporter US Volume 32.1
Keywords: Adsorption, Antibiotics, Carcinogens, Gas chromatography, Gas chromatography mass spectrometry, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Pesticides, Phase transitions, Precipitation, Sample preparations, Solid phase extractions, Solvents

Protocols

Enzymatic Assay of Chloramphenicol Acetyltransferase

1. OBJECTIVE To standardize a procedure for the determination of the enzymatic assay of Chloramphenicol Acetyltransferase.
Keywords: Enzyme activity, Enzymology, Extinction coefficient

Transforming E. coli with Engineered Plasmid

Inoue and colleagues developed this method in 1990. It works well for many strains commonly used in cloning. The original method calls for growing the overnight E. coli cultures at 18°C. We find that...
Keywords: Antibiotics, Centrifugation, Cloning, Peptide synthesis, Phase transitions, transformation

Peer-Reviewed Papers

References

Set your institution to view full text papers.

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It is time to stop using topical chloramphenicol. Smith JR, Wesselingh S, and Coster DJ Aust. N. Z. J. Ophthalmol. 25(1), 83-8, (1997)

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Chloramphenicol. Vining LC and Stuttard C Biotechnology 28, 505-30, (1995)

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Symposium on antimicrobial therapy. X. Chloramphenicol, clindamycin, and metronidazole. Greenfield RA J. Okla. State Med. Assoc. 86(7), 336-41, (1993)

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Chloramphenicol use and susceptibility patterns in Israel: a national survey. Nitzan O, Kennes Y, Colodner R, et al. Isr. Med. Assoc. J. 17(1), 27-31, (2015)

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The innate growth bistability and fitness landscapes of antibiotic-resistant bacteria. Deris JB, Kim M, Zhang Z, et al. Science 342(6162), 1237435, (2013)

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Chloramphenicol eye drops in the treatment of conditions indicative of maxillary sinusitis. Nielsen IR, Seim A, and Bentzen N Tidsskr. Nor. Laegeforen. 133(20), 2146-8, (2013)

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Restricting topical ocular chloramphenicol eye drop use in the United States. Did we overreact? Fraunfelder FW and Fraunfelder FT Am. J. Ophthalmol. 156(3), 420-2, (2013)

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Improvement of pBBR1MCS plasmids, a very useful series of broad-host-range cloning vectors. Obranić S, Babić F, and Maravić-Vlahoviček G Plasmid 70(2), 263-7, (2013)

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Reaction or infection: topical chloramphenicol treatment. Livingston RJ, Butterworth JW, and Belt P Ann. R. Coll. Surg. Engl. 95(1), e20-1, (2013)

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Resistance of Bacteroides isolates recovered among clinical samples from a major Costa Rican hospital between 2000 and 2008 to ß-lactams, clindamycin, metronidazole, and chloramphenicol. Cordero-Laurent E, Rodríguez C, Rodríguez-Cavallini E, et al. Rev. Esp. Quimioter. 25(4), 261-5, (2012)

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Gingival pain: an unusual side effect of ziprasidone. Raghunath A BMJ Case Rep. 2013, doi:10.1136/bcr-2012-007577, (2013)

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Towards evidence-based emergency medicine: best BETs from the Manchester Royal Infirmary. BET 3: Fucidic acid or chloramphenicol for neonates with sticky eyes. Grayson A and Wylie K Emerg. Med. J. 28(7), 634, (2011)

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Topical chloramphenicol for eye infections. Lam RF, Lai JS, Ng JS, et al. Hong Kong Med. J. 8(1), 44-7, (2002)

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[Neurotoxicity of antibacterial agents (tetracyclines, chloramphenicol, aminoglycosides, beta-lactams and others)]. Kanemitsu K and Shimada J Ryoikibetsu. Shokogun. Shirizu. (27 Pt 2), 545-51, (1999)

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Ophthalmic chloramphenicol: a review of the literature. Field D, Martin D, and Witchell L Accid. Emerg. Nurs. 7(1), 13-7, (1999)

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Molecular basis of bacterial resistance to chloramphenicol and florfenicol. Schwarz S, Kehrenberg C, Doublet B, et al. FEMS Microbiol. Rev. 28(5), 519-42, (2004)

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A new triterpenoid from Alisma orientale and their antibacterial effect. Jin HG, Jin Q, Ryun Kim A, et al. Arch. Pharm. Res. 35(11), 1919-26, (2012)

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Thermal acclimation of the symbiotic alga Symbiodinium spp. alleviates photobleaching under heat stress. Takahashi S, Yoshioka-Nishimura M, Nanba D, et al. Plant Physiol. 161(1), 477-85, (2013)

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Molecular evidence for spread of two major methicillin-resistant Staphylococcus aureus clones with a unique geographic distribution in Chinese hospitals. Yudong Liu et al Antimicrob. Agents Chemother. 53, 512-8, (2009)

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Genetic and structural insights into the dissemination potential of the extremely broad-spectrum class A β-lactamase KPC-2 identified in an Escherichia coli strain and an Enterobacter cloacae strain isolated from the same patient in France. Stephanie Petrella et al Antimicrob. Agents Chemother. 52, 3725-36, (2008)

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Rapid antimicrobial susceptibility testing by sensitive detection of precursor rRNA using a novel electrochemical biosensing platform. Halford C, Gonzalez R, Campuzano S, et al. Antimicrob. Agents Chemother. 57(2), 936-43, (2013)

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Establishment of magnetic beads-based enzyme immunoassay for detection of chloramphenicol in milk. Xu J, Yin W, Zhang Y, et al. Food Chem. 134(4), 2526-31, (2012)

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High error rates in selenocysteine insertion in mammalian cells treated with the antibiotic doxycycline, chloramphenicol, or geneticin. Tobe R, Naranjo-Suarez S, Everley RA, et al. J. Biol. Chem. 288(21), 14709-15, (2013)

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Magnetic molecularly imprinted polymer extraction of chloramphenicol from honey. Chen L and Li B Food Chem. 141(1), 23-8, (2013)

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Single-step selection of drug resistant Acinetobacter baylyi ADP1 mutants reveals a functional redundancy in the recruitment of multidrug efflux systems. Brzoska AJ, Hassan KA, de Leon EJ, et al. PLoS ONE 8(2), e56090, (2013)

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Clindamycin, metronidazole, and chloramphenicol. Kasten MJ Mayo Clin. Proc. 74(8), 825-33, (1999)

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O-Acetyltransferases for chloramphenicol and other natural products. Murray IA and Shaw WV Antimicrob. Agents Chemother. 41(1), 1-6, (1997)

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Modulation of mitochondrial capacity and angiogenesis by red wine polyphenols via estrogen receptor, NADPH oxidase and nitric oxide synthase pathways. Duluc L, Jacques C, Soleti R, et al. Int. J. Biochem. Cell Biol. 45(4), 783-91, (2013)

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Structure of a dinuclear iron cluster-containing β-hydroxylase active in antibiotic biosynthesis. Makris TM, Knoot CJ, Wilmot CM, et al. Biochemistry 52(38), 6662-71, (2013)

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Metabolism of chloramphenicol: a story of nearly 50 years. Bories GF and Cravedi JP Drug Metab. Rev. 26(4), 767-83, (1994)

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Study on the binding of chloroamphenicol with bovine serum albumin by fluorescence and UV-vis spectroscopy. Zhang J, Chen L, Zeng B, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 105, 74-9, (2013)

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Structural, electronic, thermodynamical and charge transfer properties of Chloramphenicol Palmitate using vibrational spectroscopy and DFT calculations. Mishra R, Srivastava A, Sharma A, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 101, 335-42, (2013)

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Synthesis and in-vitro antimicrobial evaluation of a high-affinity iron chelator in combination with chloramphenicol. Zhu CF, Qiu DH, Kong XL, et al. J. Pharm. Pharmacol. 65(4), 512-20, (2013)

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Physico-chemical factors affect chloramphenicol efflux and EmhABC efflux pump expression in Pseudomonas fluorescens cLP6a. Adebusuyi A and Foght J Res. Microbiol. 164(2), 172-80, (2013)

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Influence of dTMP on the phenotypic appearance and intracellular persistence of Staphylococcus aureus. Zander J Infect. Immun. 76(4), 1333-9, (2008)

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Determination of chloramphenicol in aquatic products by graphene-based SPE coupled with HPLC-MS/MS. Wu J, Chen L, Mao P, et al. J. Sep. Sci. 35(24), 3586-92, (2012)

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Major haplotypes of the human bitter taste receptor TAS2R41 encode functional receptors for chloramphenicol. Thalmann S, Behrens M, and Meyerhof W Biochem. Biophys. Res. Commun. 435(2), 267-73, (2013)

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Chloramphenicol: a review. Balbi HJ Pediatr. Rev. 25(8), 284-8, (2004)

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Chloramphenicol eye drops: a dangerous drug? Diamond J and Leeming J Practitioner 239(1555), 608-11, (1995)

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Reductive degradation of chloramphenicol using bioelectrochemical system (BES): a comparative study of abiotic cathode and biocathode. Sun F, Liu H, Liang B, et al. Bioresour. Technol. 143, 699-702, (2013)

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The effects of chloramphenicol on Ulva lactuca. Leston S, Nunes M, Viegas I, et al. Chemosphere 91(4), 552-7, (2013)

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Fast HPLC-DAD quantification procedure for selected sulfonamids, metronidazole and chloramphenicol in wastewaters using second-order calibration based on MCR-ALS. Vosough M and Mashhadiabbas Esfahani H Talanta 113, 68-75, (2013)

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Initial treatment of Pseudomonas aeruginosa contact lens-associated keratitis with topical chloramphenicol, and effect on outcome. Bourkiza R, Kaye S, Bunce C, et al. Br. J. Ophthalmol. 97(4), 429-32, (2013)

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An overview of highly optically pure chloramphenicol bases: applications and modifications. Yang K, Fang H, Gong J, et al. Mini Rev. Med. Chem. 9(11), 1329-41, (2009)

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Ocular chloramphenicol and aplastic anaemia. Is there a link? Rayner SA and Buckley RJ Drug Saf. 14(5), 273-6, (1996)

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Response of bacterial isolates from Antarctic shallow sediments towards heavy metals, antibiotics and polychlorinated biphenyls. Lo Giudice A, Casella P, Bruni V, et al. Ecotoxicology 22(2), 240-50, (2013)

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Chloramphenicol toxicity. Holt D, Harvey D, and Hurley R Adverse Drug React. Toxicol. Rev. 12(2), 83-95, (1993)

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Ocular penetration of topical antibiotics: study on the penetration of chloramphenicol, tobramycin and netilmicin into the anterior chamber after topical administration. Cagini C, Piccinelli F, Lupidi M, et al. Clin. Experiment. Ophthalmol. 41(7), 644-7, (2013)

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On the use of the antibiotic chloramphenicol to target polypeptide chain mimics to the ribosomal exit tunnel. Mamos P, Krokidis MG, Papadas A, et al. Biochimie 95(9), 1765-72, (2013)

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Sinus tract identification by Methylene Blue gel. Strevinas A, Reid AJ, and McGrouther DA J. Plast. Reconstr. Aesthet. Surg. 66(10), e297, (2013)

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Characteristics of Staphylococcus aureus small colony variant and its parent strain isolated from chronic mastitis at a dairy farm in Beijing, China. Alkasir R, Liu X, Zahra M, et al. Microb. Drug Resist. 19(2), 138-45, (2013)

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Real-time assessment of the microbial quality of retail shrimp using CO2 evolution rate. Alderees F and Hsieh YH J. Food Prot. 75(12), 2190-6, (2012)

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Scrub typhus pneumonitis. Premaratna R, Ariyaratna N, Botheju WI, et al. Int. J. Infect. Dis. 17(4), e284, (2013)

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Determination of chloramphenicol in honey, milk, and egg by liquid chromatography/mass spectrometry: single-laboratory validation. Ozcan N and Aycan O J. AOAC Int. 96(5), 1158-63, (2013)

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Immunoaffinity column cleanup with LC/MS/MS for the determination of chloramphenicol in honey and prawns: single-laboratory validation. Mackie J, Marley E, and Donnelly C J. AOAC Int. 96(4), 910-6, (2013)

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Determination of chloramphenicol residues in aquatic products using immunoaffinity column cleanup and high performance liquid chromatography with ultraviolet detection. Zhang QJ, Peng T, Chen DD, et al. J. AOAC Int. 96(4), 897-901, (2013)

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A simple method for the detection of Leptolegnia chapmanii from infected Aedes aegypti larvae. Leles RN, López Lastra CC, García JJ, et al. Can. J. Microbiol. 59(6), 425-9, (2013)

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Epidemiologic Study of Malassezia Yeasts in Acne Patients by Analysis of 26S rDNA PCR-RFLP. Song YC, Hahn HJ, Kim JY, et al. Ann. Dermatol. 23(3), 321-8, (2011)

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Chloramphenicol in the 21st century. Wareham DW and Wilson P Hosp. Med. 63(3), 157-61, (2002)

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Characterization of cost with respect to nutritional upshift in the media composition along with sublethal doses of transcriptional and translational inhibitor. Malakar P Arch. Microbiol. 196(4), 289-94, (2014)

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Merck 14,2077

Beil. 13,IV,2742

Aldrich MSDS 1, 364:D / Corp MSDS 1 (1), 722:C / FT-IR 2 (2), 2987:A / FT-IR 1 (2), 362:D / FT-NMR 1 (2), 1380:A / IR-Spectra (3), 1074:A / IR-Spectra (2), 939:D / NMR-Reference 2 (2), 340:B / RegBook 1 (2), 2011:G / Sax 6, 668 / Sigma FT-IR 1 (1), 634:C / Structure Index 1, 321:A:2

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