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Home > Encyclopedia > Chloramphenicol palmitate

Chloramphenicol palmitate

pharmaceutical raw materials
Chloramphenicol palmitate structure

Chloramphenicol palmitate 

structure
  • CAS No:

    530-43-8

  • Formula:

    C27H42Cl2N2O6

  • Chemical Name:

    Chloramphenicol palmitate

  • Synonyms:

    Hexadecanoic acid,(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester;Palmitic acid,α-ester with D-threo-(-)-2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]acetamide;Hexadecanoic acid,2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester,[R-(R*,R*)]-;Palmitic acid,ester with chloramphenicol;Hexadecanoic acid,(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester;Acetamide,2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-,α-palmitate,D-threo-;Chloramphenicol palmitate;Chloramphenicol palmitate (ester);D-(-)-Chloramphenicol palmitate;Detreopal;Chloramphenicol monopalmitate (ester);Chloramphenicol monopalmitate;Chloromycetin palmitate;Chloramphenicol α-palmitate;Clorolifarina;Chlorambon;Chloropal;27380-50-3;52136-72-8;74283-44-6

  • Categories:

    Analytical Chemistry  >  Analysis Reagents

Description

white crystals


Chloramphenicol palmitate is a hexadecanoate ester. It derives from a chloramphenicol.

Chloramphenicol palmitate Basic Attributes

561.54

561.54

208-477-9

43VU4207NW

DTXSID9048699

29414000

Characteristics

121.45000

9.04

1.2±0.1 g/cm3

90 °C

691.6±55.0 °C at 760 mmHg

372.1±31.5 °C

1.526

8.423ug/L(25 ºC)

Store at RT.

Oral-Mouse LD50: 2640 mg/kg

Thermal decomposition releases toxic nitrogen oxides and chloride fumes

D26 +24.6° (c = 5 in ethanol)

Safety Information

NONH for all modes of transport

3

40-36/37/38-20/21/22

36/37-36-26

RT4735000

Xn

The warehouse is low-temperature, ventilated and dry

P280

H351

Toxicity

moderately toxic

Drug Information

chloramphenicol monopalmitate

Chloramphenicol palmitate Use and Manufacturing

Methods of Manufacturing

Add α-picoline and benzene to the reaction pot, add chloramphenicol with stirring, keep 32-37°C, and add palmitoyl chloride dropwise. After the addition is complete, continue to stir for 4h and add to 15 times the water to precipitate the crude product. The crude product is washed, decolorized and recrystallized to obtain odorless chloramphenicol.

Uses

Chloramphenicol palmitate is prepared by acylation of chloramphenicol with palmitic acid. Although chloramphenicol palmitate is a more hydrophobic drug which should enhance bioavailability, the primary advantage of the ester is to mask the taste of chloramphenicol in oral formulations. Chloramphenicol palmitate is significantly less active than chloramphenicol but acts as a prodrug, being readily hydrolysed by acid and esterase in the gut to release chloramphenicol.

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:561.5
XLogP3:9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:21
Exact Mass:560.2419925
Monoisotopic Mass:560.2419925
Topological Polar Surface Area:121
Heavy Atom Count:37
Complexity:639
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is the palmitate of chloramphenicol. It has no antibacterial activity in vitro. After oral administration, it is hydrolyzed into chloramphenicol by pancreatic lipase in the duodenum and absorbed into the body to exert its antibacterial effect. It has antibacterial activity against aerobic Gram-negative bacteria and Gram-positive bacteria, anaerobic bacteria, Rickettsia, spirochetes and Chlamydia. It only has antibacterial effect on the following bacteria: Staphylococcus aureus, Streptococcus pyogenes, Streptococcus viridans, Group B soluble Streptococcus, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Salmonella typhi, Salmonella paratyphi, Shigella, Bacteroides fragilis and other anaerobic bacteria. It has bactericidal effect on the following bacteria: Haemophilus influenzae, Streptococcus pneumoniae and Neisseria meningitidis. 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 enters bacterial cells by diffusion, and reversibly binds to the 50S subunit of the bacterial ribosome, which blocks the growth of the peptide chain (possibly due to the inhibition of the action of transpeptidase), thereby inhibiting the formation of the peptide chain 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

  • MAHIMA LIFE SCIENCES PRIVATE LTD

    United States United States
    Active
  • PARKE DAVIS DIV WARNER LAMBERT CO

    United States United States
    Inactive
  • QUIMICA SINTETICA SA

    Spain Spain
    Inactive

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