chloramphenicol (PAMDB110038)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110038
Identification
Name: chloramphenicol
Description:An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:

• Chloramex

• Chloramphenicolum

• Chlornitromycin

• Chlorocid

• Chlorocol

• Chloromycetin

• Cloramfenicol

• D-(-)-2,2-dichloro-N-(beta-Hydroxy-alpha-(hydroxymethyl)-P-nitrophenylethyl)acetamide

• D-(-)-threo-1-P-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol

• Fenicol

• Globenicol

• Halomycetin

• Laevomycetinum

• Levomicetina

• Levomycetin

• Oleomycetin

• Sificetina

• D-(-)-2,2-dichloro-N-(b-Hydroxy-a-(hydroxymethyl)-P-nitrophenylethyl)acetamide

• D-(-)-2,2-dichloro-N-(?-hydroxy-?-(hydroxymethyl)-P-nitrophenylethyl)acetamide

• CAF

• CAP

• Chloramfenikol

• Chloramphenicole

• Chloroamphenicol

• Cloroamfenicolo

• D-Chloramphenicol

• Detreomycin

• Kloramfenikol

• Cloranfenicol

• Ophthochlor

• Syntomycin

Chemical Formula: C11H12N2O5Cl2
Average Molecular Weight: 323.13
Monoisotopic Molecular Weight: 322.0123269261
InChI Key: WIIZWVCIJKGZOK-UHFFFAOYSA-N
InChI: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)
CAS number: 56-75-7
IUPAC Name:2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Traditional IUPAC Name: chloramphenicol
SMILES:C(O)C(NC(=O)C(Cl)Cl)C(C1(C=CC(N(=O)=O)=CC=1))O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassNitrobenzenes
Direct Parent Nitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • C-nitro compound
  • Secondary alcohol
  • Organic nitro compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Aromatic alcohol
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Alkyl halide
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Alcohol
  • Alkyl chloride
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 150.5 °C
Experimental Properties:
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.61e-01 g/LNot Available
LogP0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.46 mg/mLALOGPS
logP1.15ALOGPS
logP0.88ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area115.38 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.2 m3·mol-1ChemAxon
Polarizability28.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [538813 ]
  • Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [1398851 ]
  • Pecoul B, Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [1681224 ]
  • Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [6464136 ]
  • Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [16039333 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
ChEBI101209
ChemSpider292
HMDBHMDB14589
KEGGC00918
NCI3069
PubChem298