Chemicals and Drugs

Chloramphenicol

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)

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

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)

Chemical Identity

Chemical Information

Molecular Formula
C11H12Cl2N2O5
Molecular Weight
323.13 g/mol
CAS Registry No.
56-75-7
IUPAC Name
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
InChIKey
WIIZWVCIJKGZOK-RKDXNWHRSA-N
SMILES
C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
MeSH Unique ID
D002701
Source
PubChem CID 5959

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

11 entry terms
  • Cloranfenicol
  • Kloramfenikol
  • Amphenicol
  • Amphenicols
  • Chlornitromycin
  • Chlorocid
  • Chloromycetin
  • Detreomycin
  • Levomycetin
  • Ophthochlor
  • Syntomycin

MeSH Record

Aspects Covered

26 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

an antibiotic

MeSH Hierarchy

Tree Numbers

  1. D02w.033w.455.706.300w
  2. D02w.455w.426w.559w.389.565w.175w
  3. D02w.640w.529w.175w

MeSH Record

NLM Classification

QV 350.5.C5

AMA Style

References

  1. National Library of Medicine. Chloramphenicol. Medical Subject Headings (MeSH). 2026. Unique ID D002701. http://id.nlm.nih.gov/mesh/2026/D002701
  2. Chloramphenicol. In: Wikipedia. https://en.wikipedia.org/wiki/Chloramphenicol
  3. Chloramphenicol. In: Wikidata. https://www.wikidata.org/wiki/Q274515
  4. Chloramphenicol. In: PubChem Compound. CID 5959. https://pubchem.ncbi.nlm.nih.gov/compound/5959