Chloramphenicol

Chloramphenicol

Clinical data
Trade names	Pentamycetin, Chloromycetin
AHFS/Drugs.com	Monograph
MedlinePlus	a608008
License data	US FDA: Chloramphenicol
Pregnancy category	AU: A US: C (Risk not ruled out)
Routes of administration	Topical (eye drops), by, IV, IM
ATC code	D06AX02 (WHO) D10AF03 (WHO) G01AA05 (WHO) J01BA01 (WHO) S01AA01 (WHO) S02AA01 (WHO) S03AA08 (WHO) QJ51BA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	75–90%
Protein binding	60%
Metabolism	Liver
Biological half-life	1.6-3.3 hours
Excretion	Kidney (5-15%), faeces (4%)
Identifiers
IUPAC name 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
CAS Number	56-75-7 Y
PubChem (CID)	298
DrugBank	DB00446 Y
ChemSpider	5744 Y
UNII	66974FR9Q1 Y
KEGG	D00104 Y
ChEBI	CHEBI:17698 Y
ChEMBL	CHEMBL130 Y
ECHA InfoCard	100.000.262
Chemical and physical data
Formula	C11H12Cl2N2O5
Molar mass	323.1320 g/mol
3D model (Jmol)	Interactive image
SMILES c1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
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)/t8-,9-/m1/s1 Y Key:WIIZWVCIJKGZOK-RKDXNWHRSA-N Y

Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections. This includes meningitis, plague, cholera, and typhoid fever. Its use 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. It is available intravenously, by mouth, and as an eye ointment.

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 children 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 in 1947. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world of an intravenous dose is about 0.40 to 1.90 USD. In the United States it is very expensive. Global issues relating to bacterial resistance have revived interest in its use.

The original indication of chloramphenicol was in the treatment of typhoid, but the now almost universal presence of multiple drug-resistant Salmonella typhi has meant it is seldom used for this indication except when the organism is known to be sensitive. Chloramphenicol may be used as a second-line agent in the treatment of tetracycline-resistant cholera.