Chloramphenicol palmitate

Names

[ CAS No. ]:
530-43-8

[ Name ]:
Chloramphenicol palmitate

[Synonym ]:
Chlorambon
detreopal
CHLORAMPHENICOLPALMITATE,BP
cap-palmitate
Chloramphenicol palmitate
Clorolifarina
chloromycetinpalmitate
Hexadecanoic acid, (2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester
CHLORAMPHENICAL PALMITATE
(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl hexadecanoate
D-threo-(-)-2,2-Dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl)acetamide α-palmitate
EINECS 208-477-9
MFCD00083597
CAP-P
Chloramphenicol palmitate (ester)
chloramphenicol 3'-palmitate
(2R,3R)-2-[(Dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl palmitate
[R-(R*,R*)]-Hexadecanoic Acid 2-[(Dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl Ester
Chloropal
D-threo-(-)-2,2-Dichloro-N-(b-hydroxy-a-(hydroxymethyl)-p-nitrophenethyl)acetamide a-Palmitate
chlorophenicol palmitate

Biological Activity

[Description]:

Chloramphenicol palmitate is an orally active broad spectrum antibiotic and has a broad spectrum of activity against gram positive and gram negative bacteria. Chloramphenicol palmitate inhibits bacterial protein synthesis by blocking the peptidyl transferase step. Chloramphenicol palmitate can be used as bacterial selection agent in transformed cells containing chloramphenicol resistance genes[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Siti Nani Nurbaeti, et al. Sustained-release Microparticle Dry Powders of Chloramphenicol Palmitate or Thiamphenicol Palmitate Prodrugs for Lung Delivery as Aerosols.Eur J Pharm Sci. 2019 Oct 1;138:105028.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
691.6±55.0 °C at 760 mmHg

[ Melting Point ]:
90ºC

[ Molecular Formula ]:
C₂₇H₄₂Cl₂N₂O₆

[ Molecular Weight ]:
561.538

[ Flash Point ]:
372.1±31.5 °C

[ Exact Mass ]:
560.242004

[ PSA ]:
121.45000

[ LogP ]:
9.04

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.526

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RT4735000

CHEMICAL NAME :: Palmitic acid, alpha-ester with D-threo-(-)-2,2-dichloro-N-(beta-hydroxy-alpha- (hydroxymethyl)-p-nitrophenethyl)acetamide

CAS REGISTRY NUMBER :: 530-43-8

BEILSTEIN REFERENCE NO. :: 2826438

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C27-H42-Cl2-N2-O6

MOLECULAR WEIGHT :: 561.61

WISWESSER LINE NOTATION :: WNR DYQY1OV15&MVYGG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2640 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,248,1982 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1200 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: VHAGAS Verhandlungen der Anatomischen Gesellschaft. (VEB Gustav Fischer Verlag, Postfach 176, Jena, DDR-6900, Ger. Dem. Rep.) V.1- 1887- Volume(issue)/page/year: 71,623,1977 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2340 No. of Facilities: 79 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 318 (estimated) No. of Female Employees: 132 (estimated)

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H351

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R40

[ Safety Phrases ]:
36/37-36-26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RT4735000

[ HS Code ]:
29414000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Structural, electronic, thermodynamical and charge transfer properties of Chloramphenicol Palmitate using vibrational spectroscopy and DFT calculations.

Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 101 , 335-42, (2013)

The global problem of advancing bacterial resistance to newer drugs has led to renewed interest in the use of Chloramphenicol Palmitate (C27H42Cl2N2O6) [Palmitic acid alpha ester with D-threo-(-),2-di...

Metabolism of some drugs by intestinal lactobacilli and their toxicological considerations.

Acta Pharmacol. Toxicol. (Copenh.) 58(1) , 11-5, (1986)

The bacterial metabolism of three drugs (sulphasalazine, phthalylsulphathiazole and chloramphenicol palmitate) and two dyes (tartrazine and methyl red) has been studied using a resting culture techniq...

The effect of exocrine pancreatic function on chloramphenicol pharmacokinetics in patients with cystic fibrosis.

Pediatr. Res. 23(4) , 388-92, (1988)

The effect of exocrine pancreatic function on the pharmacokinetics of the choramphenicol oral capsule (CAP-base), chloramphenicol palmitate oral liquid (CAP-P), and chloramphenicol succinate intraveno...