Chloramphenicol

Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections. This includes use as an eye ointment to treat conjunctivitis. By mouth or by injection into a vein, it is used to treat meningitis, plague, cholera, and typhoid fever. Its use by mouth or by injection is only recommended when safer antibiotics cannot be used. Monitoring both blood levels of the medication and blood cell levels every two days is recommended during treatment.

Chloramphenicol
Clinical data
Trade namesChloromycetin, Abeed, others
Other namesC/CHL/CL
AHFS/Drugs.comMonograph
MedlinePlusa608008
License data
Pregnancy
category
  • AU: A
Routes of
administration
Topical (eye drops), by mouth, intravenous therapy (IV), intramuscular injection (IM)
ATC code
Legal status
Legal status
  • AU: S3 (Pharmacist only)
  • CA: ℞-only
  • UK: P (Pharmacy medicines) / POM
  • US: WARNINGRx-only
Pharmacokinetic data
Bioavailability75–90%
Protein binding60%
MetabolismLiver
Elimination half-life1.6–3.3 hours
ExcretionKidney (5–15%), faeces (4%)
Identifiers
  • 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.262
Chemical and physical data
FormulaC11H12Cl2N2O5
Molar mass323.13 g·mol−1
3D model (JSmol)
SMILES
  • c1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
  • 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)/t8-,9-/m1/s1 Y
  • Key:WIIZWVCIJKGZOK-RKDXNWHRSA-N Y
  (verify)

Common side effects include bone marrow suppression, nausea, and diarrhea. The bone marrow suppression may result in death. To reduce the risk of side effects treatment duration should be as short as possible. People with liver or kidney problems may need lower doses. In young infants, a condition known as gray baby syndrome may occur which results in a swollen stomach and low blood pressure. Its use near the end of pregnancy and during breastfeeding is typically not recommended. Chloramphenicol is a broad-spectrum antibiotic that typically stops bacterial growth by stopping the production of proteins.

Chloramphenicol was discovered after being isolated from Streptomyces venezuelae in 1947. Its chemical structure was identified and it was first synthesized in 1949. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

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