ChemicalBook > CAS DataBase List > Chloramphenicol palmitate

Chloramphenicol palmitate

Product Name
Chloramphenicol palmitate
CAS No.
530-43-8
Chemical Name
Chloramphenicol palmitate
Synonyms
cap-p;detreopal;Chloropal;Chlorambon;cap-palmitate;Clorolifarina;chloromycetinpalmitate;CHLORAMPHENICOL PALMITATE;CHLORAMPHENICAL PALMITATE;Chloramphenicol Impurity 2
CBNumber
CB0437291
Molecular Formula
C27H42Cl2N2O6
Formula Weight
561.54
MOL File
530-43-8.mol
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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.
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H351Suspected of causing cancer

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1107401
Product name
Chloramphenicol palmitate nonpolymorph A
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$860
Updated
2024/03/01
Sigma-Aldrich
Product number
1107300
Product name
Chloramphenicol palmitate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$420
Updated
2024/03/01
Sigma-Aldrich
Product number
46109
Product name
Chloramphenicol palmitate
Purity
VETRANAL?, analytical standard
Packaging
100mg
Price
$22.1
Updated
2022/05/15
Cayman Chemical
Product number
26663
Product name
Chloramphenicol Palmitate
Packaging
5mg
Price
$108
Updated
2024/03/01
Cayman Chemical
Product number
26663
Product name
Chloramphenicol Palmitate
Packaging
25mg
Price
$402
Updated
2024/03/01
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Chloramphenicol palmitate Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

2-Picoline Chloramphenicol Benzene Thionyl chloride Palmitic acid Palmitoyl chloride

Preparation Products

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View Lastest Price from Chloramphenicol palmitate manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Chloramphenicol palmitate 530-43-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11
Shaanxi Dideu Medichem Co. Ltd
Product
Chloramphenicol palmitate 530-43-8
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%
Supply Ability
500 MT
Release date
2020-05-25
Career Henan Chemical Co
Product
1-[4-(2-Hydroxyethyl)phenoxy]-2,3-epoxypropane 63659-17-6
Price
US $1.00/ASSAYS
Min. Order
1ASSAYS
Purity
85.0-99.8%
Supply Ability
20 tons
Release date
2019-12-24

530-43-8, Chloramphenicol palmitateRelated Search:

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

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  • Chloramphenicol Palmitat e Polymorph A (100 mg)
  • Chloramphenicol palmitate polymorph A
  • Chloramphenicol palmitate nonpolymorph A
  • 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
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  • Chloramphenicol Palmitate (1107300)
  • C11121000 ChloramphenicoLpalmitate
  • 530-43-8
  • C27H42Cl2N2O6
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