Chloramphenicol palmitate
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Chloramphenicol palmitate
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CAS No:
530-43-8
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Formula:
C27H42Cl2N2O6
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Chemical Name:
Chloramphenicol palmitate
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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
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CAS No:
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
Chloramphenicol palmitate Use and 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.
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.
Registered Holders
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MAHIMA LIFE SCIENCES PRIVATE LTD
Active
United States
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PARKE DAVIS DIV WARNER LAMBERT CO
Inactive
United States
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QUIMICA SINTETICA SA
Inactive
Spain
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