Chloramphenicol
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| Category | Antibiotics |
| Catalog number | BBF-00635 |
| CAS | 56-75-7 |
| Molecular Weight | 323.13 |
| Molecular Formula | C11H12Cl2N2O5 |
| Purity | >98% |
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Description
It is produced by the strain of Streptormyces venezuelae. Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections.
Specification
| Synonyms | Chloromycetin; Halomycetin; Levomicetina |
| Storage | -20°C |
| IUPAC Name | 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| Canonical SMILES | C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-] |
| InChI | InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1 |
| InChI Key | WIIZWVCIJKGZOK-RKDXNWHRSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White to Off-white Solid |
| Application | It is effective against tetracycline-resistant vibrios. |
| Melting Point | 147-152 °C |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
| LogP | 1.14 |
Toxicity
| Carcinogenicity | 2A, probably carcinogenic to humans. |
| Mechanism Of Toxicity | Chloramphenicol targets the large 39S subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result chloramphenicol is cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. The likely target of chloramphenicol is the 16S rRNA molecule in the mitochondrial ribosome, which is analogous to the 23S rRNA in bacterial ribosomes. |
| Toxicity | LD50 = 1500 mg/kg (Oral, mouse); LD50 = 2500 mg/kg (Oral, rat). |
Reference Reading
1.Green synthesized gold nanoparticles decorated graphene oxide for sensitive determination of chloramphenicol in milk, powdered milk, honey and eye drops.
Karthik R1, Govindasamy M1, Chen SM2, Mani V3, Lou BS4, Devasenathipathy R5, Hou YS1, Elangovan A6. J Colloid Interface Sci. 2016 Apr 27;475:46-56. doi: 10.1016/j.jcis.2016.04.044. [Epub ahead of print]
A simple and rapid green synthesis using Bischofia javanica Blume leaves as reducing agent was developed for the preparation of gold nanoparticles (AuNPs). AuNPs decorated graphene oxide (AuNPs/GO) was prepared and employed for the sensitive amperometric determination of chloramphenicol. The green biosynthesis requires less than 40s to reduce gold salts to AuNPs. The formations of AuNPs and AuNPs/GO were evaluated by scanning electron and atomic force microscopies, UV-Visible and energy dispersive X-ray spectroscopies, X-ray diffraction studies, and electrochemical methods. AuNPs/GO composite film modified electrode was fabricated and shown excellent electrocatalytic ability towards chloramphenicol. Under optimal conditions, the amperometric sensing platform has delivered wide linear range of 1.5-2.95μM, low detection limit of 0.25μM and high sensitivity of 3.81μAμM-1cm-2. The developed sensor exhibited good repeatability and reproducibility, anti-interference ability and long-term storage stability.
2.Polyamino-Isoprenic Derivatives Block Intrinsic Resistance of P. aeruginosa to Doxycycline and Chloramphenicol In Vitro.
Borselli D1, Lieutaud A1, Thefenne H1,2, Garnotel E1,2, Pagès JM1, Brunel JM3, Bolla JM1. PLoS One. 2016 May 6;11(5):e0154490. doi: 10.1371/journal.pone.0154490. eCollection 2016.
Multidrug resistant bacteria have been a worldwide concern for decades. Though new molecules that effectively target Gram-positive bacteria are currently appearing on the market, a gap remains in the treatment of infections caused by Gram-negative bacteria. Therefore, new strategies must be developed against these pathogens. The aim of this study was to select an antibiotic for which a bacterium is naturally resistant and to use an escort molecule to restore susceptibility, similarly to the model of β-lactam/ β-lactamase inhibitors. High-content screening was performed on the reference strain PA01, allowing the selection of four polyamino-isoprenic compounds that acted synergistically with doxycycline. They were assayed against clinical isolates and Multi-Drug-Resistant strains. One of these compounds was able to decrease the MIC of doxycycline on the reference strain, efflux pump overproducers and clinical isolates of P. aeruginosa, to the susceptibility level.
3.Determination of chloramphenicol, thiamphenicol, florfenicol and florfenicol amine in poultry, swine, bovine and fish by liquid chromatography-tandem mass spectrometry.
Barreto F1, Ribeiro C2, Barcellos Hoff R3, Dalla Costa T4. J Chromatogr A. 2016 Apr 16. pii: S0021-9673(16)30430-7. doi: 10.1016/j.chroma.2016.04.024. [Epub ahead of print]
A simple, rapid and sensitive method for confirmatory and quantitative purposes using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) was developed and validated for determination of chloramphenicol, thiamphenicol, florfenicol and its metabolite, florfenicol amine, in poultry, swine, bovine and fish muscle. Sample preparation was based on extraction with organic solvent (ethyl acetate: ammonium hydroxide, 98:2) followed by evaporation and fat removal using hexane. The chromatographic separation was carried out with an XTerra C18 column with a gradient elution using water and acetonitrile both with 2mM of ammonium acetate. Mass spectrometry with electrospray ionization was operated in positive or negative polarity using selected-reaction monitoring (SRM) analysis mode, achieving the requirements of four identification points for each compound. Chloramphenicol-D5 was added as internal standard. Method validation was performed according to the criteria of Commission Decision 2002/657/EC.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C11H12Cl2N2O5
Molecular Weight (Monoisotopic Mass): 322.0123 Da
Molecular Weight (Avergae Mass): 323.129 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C11H12Cl2N2O5
Molecular Weight (Monoisotopic Mass): 322.0123 Da
Molecular Weight (Avergae Mass): 323.129 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C11H12Cl2N2O5
Molecular Weight (Monoisotopic Mass): 322.0123 Da
Molecular Weight (Avergae Mass): 323.129 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C11H12Cl2N2O5
Molecular Weight (Monoisotopic Mass): 322.0123 Da
Molecular Weight (Avergae Mass): 323.129 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
