530-43-8 Usage
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
Different sources of media describe the Uses of 530-43-8 differently. You can refer to the following data:
1. 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.
2. antibacterial, antirickettsial
3. 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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 530-43-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 0 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 530-43:
(5*5)+(4*3)+(3*0)+(2*4)+(1*3)=48
48 % 10 = 8
So 530-43-8 is a valid CAS Registry Number.
InChI:InChI=1/C27H42Cl2N2O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-24(32)37-20-23(30-27(34)26(28)29)25(33)21-16-18-22(19-17-21)31(35)36/h16-19,23,25-26,33H,2-15,20H2,1H3,(H,30,34)/t23-,25-/m1/s1
530-43-8Relevant articles and documents
The preparation and isolation of chloramphenicol palmitate in toluene
Daugs, Edward D.
, p. 301 - 304 (2000)
The development of a process for the preparation of the antibiotic chloramphenicol palmitate that did not use methylene chloride and that fit into the production plant with improved yields and product quality is described. Addition of DMF as a co-solvent allowed the use of toluene for the reaction and the isolation. The product distribution observed by competitive esterification at the primary and secondary hydroxyl groups of chloramphenicol was well modeled by simple expressions for parallel consecutive reactions and estimated a 1000-fold difference in the rate constants for the two sites. A small increase in the impurity levels found during production plant trials was traced to trans-esterification during the extended processing time required at the 1000-kg scale.
Substrate imprinted lipase nanogel for one-step synthesis of chloramphenicol palmitate
Wang, Rui,Zhang, Yifei,Huang, Jinhai,Lu, Diannan,Ge, Jun,Liu, Zheng
supporting information, p. 1155 - 1158 (2013/06/27)
Enzymatic catalysis with high enantio- and regio-selectivity, which is attractive for green synthesis of chemicals, often suffers from low activity in organic solvents utilized as reaction media. Here, we describe a 'substrate-imprinted' lipase nanogel that displays high activity in organic solvents. The first step was to encapsulate lipase into polyacrylamide nanogel by an aqueous in situ polymerization. Then the lipase nanogel was lyophilized in the presence of palmitic acid, a substrate of lipase, followed by extraction with petroleum ether to remove palmitic acid from the lyophilized lipase nanogel. The imprinting treatment increased the adsorption capacity of palmitic acid by 2.9-fold and the apparent activity by 2-fold in catalyzing the transesterification reaction between para-nitrophenyl palmitate and ethanol. The effects of solvent and temperature on the yield and selectivity of the enzymatic synthesis of chloramphenicol palmitate were examined, respectively. One-step synthesis of chloramphenicol palmitate with the imprinted lipase nanogel gave a yield of ～99% and a purity of ～99% within 12 hours at 20 °C, whereas the imprinted free lipase gave a yield below 60% in 20 hours. The high activity and selectivity make the substrate-imprinted enzyme nanogel an attractive catalyst for green synthesis of chemicals having complex structures.
Development of column-free alkoxycarbonyl, aryloxycarbonyl, and acyl transfer reagents
Shimizu, Mamoru,Sodeoka, Mikiko
experimental part, p. 1301 - 1312 (2009/07/05)
Easy-to-handle alkoxycarbonyl, aryloxycarbonyl, and acyl transfer reagents, which contain 3-nitro-1,2,4-triazole (NT) as a leaving group, were developed. With these reagents (NT reagents), which are stable nonhygroscopic crystalline materials, the reactions can be accomplished in about 5 min, and product can be isolated without tedious column chromatographic purification.
