Chloramphenicol Palmitate
Basic information
- CAS
530-43-8- Standard SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc([N+](=O)[O-])cc1- InChIKey
PXKHGMGELZGJQE-ILBGXUMGSA-N- Molecular formula
- C27H42Cl2N2O6
- Average molar mass
- 561.5 g/mol
- Monoisotopic mass
- 560.2419925
Overview
Chloramphenicol palmitate is a hexadecanoate ester. It is functionally related to a chloramphenicol.
Names & identifiers
- Preferred name
- Chloramphenicol Palmitate
- IUPAC
- [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] hexadecanoate
- English name
- Chloramphenicol palmitate
- Molecular formula
- C27H42Cl2N2O6
- Molecular weight
- 561.54
Names & synonyms
CHLORAMPHENICOL PALMITATE530-43-8DetreopalCAP-palmitateChloromycetin palmitateChloramphenicol monopalmitateClorolifarinaChlorambonDTXSID9048699Chlorolifarina43VU4207NWChloramphenicoli palmitas
Show more names
cap-pChloropalchloromycetinpalmitateCHLORAMPHENICAL PALMITATEChloramphenicol Impurity 2
CHEBI:3605DTXCID9028625NSC-756675Chloromycetin Palmitate Oral Suspension(2R,3R)-2-(Dichloroacetyl)amino-3-hydroxy-3-(4-nitrophenyl)propan-1-yl palmitate(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl hexadecanoate(2R,3R)-2-((dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl hexadecanoateRefChem:54772
Database identifiers
- CAS
530-43-8- PubChem CID
- 443382
- DTXSID
DTXSID9048699- ChEMBL
CHEMBL1506
Properties
Computed structural properties
- XLogP
- 9
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 21
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 639
Experimental & physicochemical properties
Animal DrugsFDA approved animal drugs -> Active ingredient
Physicochemical properties
- Melting point
- 90 C · 90 C
- alpha
- 26 · D26 +24.6° (c = 5 in ethanol)
- Boiling point
- 691.6 · 691.6±55.0 °C(Predicted)
- Density
- 1.2354 · 1.2354 (rough estimate)
- refractive index
- 1.735 · 1.7350 (estimate)
- storage temp.
- Store at RT.
- solubility
- DMSO (Slightly), Ethanol (Sparingly), Ethyl Acetate (Slightly)
- pka
- 10.69 · 10.69±0.46(Predicted)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 8.423 ug/L · 8.423ug/L(25 ºC)
- λmax
- 271 nm · 271nm(EtOH)(lit.)
- Merck
- 14 · 14,2077
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H351 (97.7%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - Hexadecanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]-: Human health tier I assessment
Hazard Classes and CategoriesCarc. 2 (97.7%)
Safety data
- wgk
- 3
- rtecs
- RT4735000
- hs_code
- 29414000
- risk_code
- 40-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 36/37-36-26
- Hazard statements
- H351
- Precautionary statements
- P280
Chemistry & industry
Applications
DescriptionChloramphenicol 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.
UsesChloramphenicol 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.
Usesantibacterial, antirickettsial
UsesChloramphenicol 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.
General DescriptionChloramphenicol 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.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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