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(-)-Chloramphenicol

pharmaceutical raw materials
(-)-Chloramphenicol structure

(-)-Chloramphenicol 

structure
  • CAS No:

    56-75-7

  • Formula:

    C11H12Cl2N2O5

  • Chemical Name:

    (-)-Chloramphenicol

  • 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

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

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

(-)-Chloramphenicol Basic Attributes

323.13

323.13

2225532

200-287-4

29414000

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

Toxicity

moderately toxic

(-)-Chloramphenicol Use and Manufacturing

Methods of 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 .

Uses

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

Downstream Products

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.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • QUIMICA SINTETICA SA

    Spain Spain
    Active
  • Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd.

    China China
    Active
  • Wuhan Wuyao Pharmaceutical Co., Ltd.

    China China
    Active

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