Chemical Component Summary

NameCHLORAMPHENICOL
Identifiers2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]ethanamide
FormulaC11 H12 Cl2 N2 O5
Molecular Weight323.129
TypeNON-POLYMER
Isomeric SMILESc1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
InChIInChI=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)/t8-,9-/m1/s1
InChIKeyWIIZWVCIJKGZOK-RKDXNWHRSA-N

Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count2
Bond Count32
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00446 
NameChloramphenicol
Groups
  • approved
  • vet_approved
  • withdrawn
DescriptionAn antibiotic first isolated from cultures of _Streptomyces venezuelae_ 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 (From Martindale, The Extra Pharmacopoeia, 29th ed, p106) The FDA has withdrawn all oral drug products containing chloramphenicol, due to the high risk of fatal aplastic anemia associated with this specific route of administration.[L43942,L44022]
Synonyms
  • Levomicetina
  • Chloramphenicolum
  • Cloranfenicol
  • Levomycetin
  • Chloramphenicol
Brand Names
  • Sopamycetin/hc Ont
  • Cebenicol Oph Liq 0.4%
  • Odan-chloramphenicol
  • Chloroptic Dps 0.5%
  • Sopamycetin Soln Otique 5%
IndicationUsed in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.
Categories
  • Alcohols
  • Amphenicols
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Topical Use
  • Anti-Bacterial Agents
ATC-Code
  • D06AX02
  • S02AA01
  • D10AF03
  • S01AA01
  • G01AA05
CAS number56-75-7

Drug Targets

NameTarget SequencePharmacological ActionActions
50S ribosomal protein L16MLQPKRTKFRKMHKGRNRGLAQGTDVSFGSFGLKAVGRGRLTARQIEAAR...unknowninhibitor
Dr hemagglutinin structural subunitMKKLAIMAAASMVFAVSSAHAGFTPSGTTGTTKLTVTEECQVRVGDLTVA...unknownantagonist
Complement decay-accelerating factorMTVARPSVPAALPLLGELPRLLLLVLLCLPAVWGDCGLPPDVPNAQPALE...unknownother
Chloramphenicol acetyltransferase 3MNYTKFDVKNWVRREHFEFYRHRLPCGFSLTSKIDITTLKKSLDDSAYKF...unknownsubstrate
Chloramphenicol acetyltransferaseMGNYFESPFRGKLLSEQVSNPNIRVGRYSYYSGYYHGHSFDDCARYLMPD...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5959
ChEMBL CHEMBL130
ChEBI CHEBI:17698