Chloramphenicol palmitate Chemical Properties

Melting point:

90 C

alpha 

D26 +24.6° (c = 5 in ethanol)

Boiling point:

691.6±55.0 °C(Predicted)

Density 

1.2354 (rough estimate)

refractive index 

1.7350 (estimate)

storage temp. 

Store at RT.

solubility 

DMSO (Slightly), Ethanol (Sparingly), Ethyl Acetate (Slightly)

pka

10.69±0.46(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

8.423ug/L(25 ºC)

λmax

271nm(EtOH)(lit.)

Merck 

14,2077

BRN 

2826438

Stability:

Hygroscopic

CAS DataBase Reference

530-43-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

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

Safety Statements 

36/37-36-26

WGK Germany 

3

RTECS 

RT4735000

HS Code 

29414000

Chloramphenicol palmitate Usage And Synthesis

Description

Chloramphenicol palmitate is an orally bioavailable ester prodrug form of the antibiotic chloramphenicol. It is hydrolyzed in the small intestine to release chloramphenicol. Formulations containing chloramphenicol palmitate were previously used in the treatment of severe bacterial infections.

Chemical Properties

white crystals

Originator

Chloromycetin,Parke Davis,US,1951

Uses

Chloramphenicol Palmitate is a Chloramphenicol (C325030) derivative, a 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.

Uses

antibacterial, antirickettsial

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.

Definition

ChEBI: Chloramphenicol palmitate is a hexadecanoate ester. It is functionally related to a chloramphenicol.

Application

Chloramphenicol palmitate was synthesized by Parke Davis Co. in 1952. It has a much less bitter taste than chloramphenicol and is suitable for oral administration, especially for children. The palmitate shows a higher serum level after oral administration than chloramphenicol does and acts the same as chloramphenicol in vivo.

Manufacturing Process

1,674 g of palmitoyl chloride is added to 1,870 g of D(-)-threo-1-pnitrophenyl-2-dichloroacetamidopropane-1,3-diol (chloramphenicol) in 2,700 cc of pyridine and the solution stirred for 1 hour. The mixture is poured into 16 liters of water and the solid collected. Recrystallization of the crude product from benzene yields the desired D(+)-threo-1-p-nitrophenyl- 1dichloroacetamido-3-palmitoyloxypropane-1-ol in pure form: MP 90°C.

brand name

Chloromycetin Palmitate (Parke- Davis).

Therapeutic Function

Antibacterial; Antirickettsial

General Description

Chloramphenicol palmitate is the palmitic acid ester ofchloramphenicol. It is a tasteless prodrug of chloramphenicolintended for pediatric use. The ester must hydrolyze invivo following oral absorption to provide the active form.Erratic serum levels were associated with early formulationsof the palmitate, but the manufacturer claims that thebioavailability of the current preparation is comparable tothat of chloramphenicol itself.

Safety Profile

Moderately toxic by oral route. An experimental teratogen. Other experimental reproductive effects. An antibiotic. When heated to decomposition it emits very toxic fumes of NOx and Cl-. See also other chloramphenicol entries.

Purification Methods

The palmitate crystallises from *benzene or xylene with m 105-106o and [] D –39.5o (c 2, Et2O), max 267.3nm. [Edgerton et al. J Am Chem Soc 77 27 1955, Beilstein 13 IV 2753.]

Chloramphenicol palmitate(530-43-8)Related Product Information

• Isopropyl palmitate
• ALTRENOGEST
• CHLOROPHOSPHONAZO III
• N-ACETYL-L-TYROSINE ETHYL ESTER
• Chloramphenicol
• Ascorbyl Palmitate
• Glycine
• Palmitic acid
• 6-Aminocaproic acid
• 3-Aminophenol
• Dichloroethane
• Thionyl chloride
• Isooctyl palmitate
• Methyl palmitate
• Vitamin A palmitate
• Acetylacetone
• Tris(hydroxymethyl)aminomethane
• Dichlorodiphenylsilane