(-)-Chloramphenicol
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(-)-Chloramphenicol
structure -
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CAS No:
56-75-7
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Formula:
C11H12Cl2N2O5
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Chemical Name:
(-)-Chloramphenicol
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Synonyms:
Acetamide,2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-;Acetamide,2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-,D-threo-(-)-;Levomycetin;Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-,[R-(R*,R*)]-;2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide;Alficetyn;Amseclor;CAF (pharmaceutical);CAM;CAP;Chemicetina;Chlomycol;Chloramphenicol;Chlorocid;Chloromycetin;Chloronitrin;Cloramicol;Clorocyn;Cloromisan;D-(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol;D-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol;Enteromycetin;Farmicetina;Globenicol;Ismicetina;Kemicetine;Klorita;Leukomyan;Levomicetina;Micloretin;Microcetina;D-(-)-threo-1-p-Nitrophenyl-2-dichloracetamido-1,3-propanediol;Novomycetin;Paraxin;Quemicetina;Sintomicetina;Sintomicetine R;Stanomycetin;Tifomycine;Treomicetina;Unimycetin;Detreomycin;I 337A;D-threo-Chloramphenicol;Chlorocidin C;CPh;Chlorocide;D-(-)-threo-Chloramphenicol;Klorocid S;D-Chloramphenicol;Chlorocidin C tetran;D-(-)-threo-1-(4-Nitrophenyl)-2-dichloroacetamido-1,3-propanediol;Chemicetin;Catilan;D-threo-(1R,2R)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediol;D-(-)-Chloramphenicol;D-(-)-threo-1-p-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol;Amphicol;Austracol;Chloramsaar;Chlorocaps;Ciplamycetin;Cloramficin;Cylphenicol;137731-90-9;15313-32-3;55172-72-0;59112-59-3;85666-84-8
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CAS No:
Description
Chloramphenicol is a broad-spectrum antibiotic.Target: AntibacterialChloramphenicol is a bacteriostatic drug that stops bacterial growth by inhibiting protein synthesis. Chloramphenicol prevents protein chain elongation by inhibiting the peptidyl transferase activity of the bacterial ribosome. It specifically binds to A2451 and A2452 residues in the 23S rRNA of the 50S ribosomal subunit, preventing peptide bond formation. While chloramphenicol and the macrolide class of antibiotics both
Characteristics
115
0.7
white powder
1.6±0.1 g/cm3
150.5-151.5 °C
Sublimes in high vacuum
14 °C
1.623
H2O: 2.5 g/L (25 º C);absolute ethanol: soluble 5-20mg/mL (as a stock solution)
2-8°C
1.73x10-12 mmHg (est)
Oral-Rat LD50: 2500 mg/kg; Oral-Mouse LD50: 1500 mg/kg
Combustion produces toxic nitrogen oxides and chloride gases
19.5 º (c=6, EtOH)
Bitter to taste
Neutral to litmus
Safety Information
IRRITANT
2811
3
45-11-39/23/24/25-23/24/25
53-45-16-36/37
AB6825000
T,F
Warehouse ventilated, low temperature and dry
In soln, chloramphenicol undergoes a number of degradative changes related to pH, temperature, photolysis and microbiological effects.
P201-P280-P308 + P313
H350
(-)-Chloramphenicol Use and Manufacturing
A large number of studies have been conducted on the production methods of chloramphenicol in various countries in the world, and they are summarized as follows: (1) p-nitroacetophenone method; (2) styrene method; (3) cinnamyl alcohol method; (4) p-nitro Cinnamon alcohol method; (5) p-nitrobenzaldehyde method. China adopts the p-nitroacetophenone method, which is obtained from chloramphenicol by nitration, oxidation, bromination, salt formation, hydrolysis, acetylation, addition, reduction, decomposition, spin-off, and dichloroacetylation of ethylbenzene .
Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial
Computed Properties
Molecular Weight:323.13
XLogP3:1.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:322.0123269
Monoisotopic Mass:322.0123269
Topological Polar Surface Area:115
Heavy Atom Count:20
Complexity:342
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
This product has a broad-spectrum antimicrobial effect in vitro, including aerobic Gram-negative and Gram-positive bacteria, anaerobes, Rickettsia, spirochetes and Chlamydia. It has bactericidal effects on the following bacteria: Haemophilus influenzae, Streptococcus pneumoniae and Neisseria meningitidis. It only has antibacterial effects on the following bacteria: Staphylococcus aureus, Streptococcus pyogenes, Streptococcus viridans, Group B hemolytic Streptococcus, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Salmonella typhi, Salmonella paratyphi, Shigella, Bacteroides fragilis and other anaerobic bacteria. The following bacteria are usually resistant to chloramphenicol: Pseudomonas aeruginosa, Acinetobacter, Enterobacter, Serratia marcescens, indole-positive Proteus, methicillin-resistant Staphylococcus and Enterococcus. This product is an antibacterial agent. Chloramphenicol is fat-soluble and its mechanism of action is to diffuse into bacterial cells and reversibly bind to the 50S subunit of bacterial ribosomes, thereby hindering the growth of peptide chains (possibly due to the inhibition of transpeptidase), thereby inhibiting the formation of peptide chains and preventing protein synthesis.
Registered Holders
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QUIMICA SINTETICA SA
Active
Spain
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Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd.
Active
China
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Wuhan Wuyao Pharmaceutical Co., Ltd.
Active
China
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