Chloramphenicol

For the episode of The Americans, see Chloramphenicol (The Americans).
Chloramphenicol
Clinical data
Trade namesChloromycetin, Abeed, others[1]
Other namesC/CHL/CL[2]
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
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[4]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.262 Edit this at Wikidata
Chemical and physical data
FormulaC11H12Cl2N2O5
Molar mass323.13 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:WIIZWVCIJKGZOK-RKDXNWHRSA-N checkY
  (verify)

Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections.[5] This includes use as an eye ointment to treat conjunctivitis.[6] By mouth or by injection into a vein, it is used to treat meningitis, plague, cholera, and typhoid fever.[5] Its use by mouth or by injection is only recommended when safer antibiotics cannot be used.[5] Monitoring both blood levels of the medication and blood cell levels every two days is recommended during treatment.[5]

Common side effects include bone marrow suppression, nausea, and diarrhea.[5] The bone marrow suppression may result in death.[5] To reduce the risk of side effects treatment duration should be as short as possible.[5] People with liver or kidney problems may need lower doses.[5] In young infants, a condition known as gray baby syndrome may occur which results in a swollen stomach and low blood pressure.[5] Its use near the end of pregnancy and during breastfeeding is typically not recommended.[7] Chloramphenicol is a broad-spectrum antibiotic that typically stops bacterial growth by stopping the production of proteins.[5]

Chloramphenicol was discovered after being isolated from Streptomyces venezuelae in 1947.[8] Its chemical structure was identified and it was first synthesized in 1949. It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication.[5]

  1. ^ Woods AL (2008). Delmar nurse's drug handbook (2009 ed.). Clifton Park, N.Y.: Delmar. p. 296. ISBN 9781428361065. Archived from the original on 2016-03-05.
  2. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  4. ^ "Chloramphenicol". PubChem. Archived from the original on 2016-11-15.
  5. ^ a b c d e f g h i j k "Chloramphenicol". The American Society of Health-System Pharmacists. Archived from the original on 2015-06-24. Retrieved Aug 1, 2015.
  6. ^ Edwards KH (2009). Optometry: Science, Techniques and Clinical Management. Elsevier Health Sciences. p. 102. ISBN 978-0750687782. Archived from the original on 2017-03-07.
  7. ^ "Chloramphenicol Pregnancy and Breastfeeding Warnings". Multum Information Services. Archived from the original on 8 September 2015. Retrieved 26 August 2015.
  8. ^ Pongs O (1979). "Chapter 3: Chloramphenicol". In Hahn FE (ed.). Mechanism of Action of Antibacterial Agents. Antibiotics Volume V Part 1. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 26–42. ISBN 978-3-642-46403-4.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.