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Chloramphenicol palmitate

Chloramphenicol palmitate Structure
Chloramphenicol palmitate
  • CAS No.530-43-8
  • Chemical Name:Chloramphenicol palmitate
  • CBNumber:CB0437291
  • Molecular Formula:C27H42Cl2N2O6
  • Formula Weight:561.54
  • MOL File:530-43-8.mol
Chloramphenicol palmitate Property
  • 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.
  • form  :neat
  • pka :10.69±0.46(Predicted)
  • Water Solubility  :8.423ug/L(25 ºC)
  • λmax :271nm(EtOH)(lit.)
  • Merck  :14,2077
  • BRN  :2826438
  • CAS DataBase Reference :530-43-8(CAS DataBase Reference)
  • FDA UNII :43VU4207NW
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H351
  • Precautionary statements P280-P281
Chloramphenicol palmitate Price More Price(7)
  • Brand: Sigma-Aldrich
  • Product number: 46109
  • Product name : Chloramphenicol palmitate
  • Purity: VETRANAL?, analytical standard
  • Packaging: 100 mg
  • Price: $19.5
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 1107300
  • Product name : Chloramphenicol palmitate
  • Purity: United States Pharmacopeia (USP) Reference Standard
  • Packaging: 200mg
  • Price: $366
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 1107401
  • Product name : Chloramphenicol palmitate nonpolymorph A
  • Purity: United States Pharmacopeia (USP) Reference Standard
  • Packaging: 200mg
  • Price: $1120
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 26663
  • Product name : Chloramphenicol Palmitate
  • Purity: 
  • Packaging: 25mg
  • Price: $396
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 26663
  • Product name : Chloramphenicol Palmitate
  • Purity: 
  • Packaging: 5mg
  • Price: $99
  • Updated: 2021/03/22
  • Buy: Buy

Chloramphenicol palmitate Chemical Properties,Usage,Production

  • Chemical Properties white crystals
  • Originator Chloromycetin,Parke Davis,US,1951
  • 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.
  • 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 Preparation Products And Raw materials
Raw materials
Preparation Products
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  • Chloramphenicol Palmitate (200 mg)
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  • ChloraMphenicol 3-palMitate
  • hexadecanoic acid [(2R,3R)-2-[(2,2-dichloro-1-oxoethyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester
  • Hexadecanoic acid, (2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester
  • Chloramphenicol Impurity 2
  • 2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propyl]acetamide Palmitate
  • D-(-)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol Palmitate
  • 530-43-8
  • C27H42Cl2N2O6
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