CHEBI:17698 - chloramphenicol

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ChEBI Name chloramphenicol
ChEBI ID CHEBI:17698
Definition An organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:13965, CHEBI:47327, CHEBI:3603, CHEBI:23106, CHEBI:23108
Supplier Information ChemicalBook:CB3364529, ChemicalBook:CB34796861, eMolecules:29538748, eMolecules:490388, Selleckchem:Chloramphenicol(Chloromycetin), ZINC000000113382
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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. 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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Formula C11H12Cl2N2O5
Net Charge 0
Average Mass 323.130
Monoisotopic Mass 322.01233
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
InChIKey WIIZWVCIJKGZOK-RKDXNWHRSA-N
SMILES C1=C([C@H]([C@H](NC(C(Cl)Cl)=O)CO)O)C=CC(=C1)[N+]([O-])=O
Metabolite of Species Details
Mycoplasma genitalium (NCBI:txid2097) Binds L16 protein of the 50S ribosomal subunit and inhibits amino acid transfer to growing peptide chains See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antibacterial drug
A drug used to treat or prevent bacterial infections.
Mycoplasma genitalium metabolite
Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing chloramphenicol (CHEBI:17698) has role Escherichia coli metabolite (CHEBI:76971)
chloramphenicol (CHEBI:17698) has role Mycoplasma genitalium metabolite (CHEBI:131604)
chloramphenicol (CHEBI:17698) has role antibacterial drug (CHEBI:36047)
chloramphenicol (CHEBI:17698) has role antimicrobial agent (CHEBI:33281)
chloramphenicol (CHEBI:17698) has role geroprotector (CHEBI:176497)
chloramphenicol (CHEBI:17698) has role protein synthesis inhibitor (CHEBI:48001)
chloramphenicol (CHEBI:17698) is a C-nitro compound (CHEBI:35716)
chloramphenicol (CHEBI:17698) is a carboxamide (CHEBI:37622)
chloramphenicol (CHEBI:17698) is a diol (CHEBI:23824)
chloramphenicol (CHEBI:17698) is a organochlorine compound (CHEBI:36683)
Incoming O-(4-trifluoroacetamidobenzylphosphonyl)chloramphenicol (CHEBI:47691) has functional parent chloramphenicol (CHEBI:17698)
O3-(2-L-lysino-2-oxoethyl)-O1-[4-(trifluoroacetamido)benzylcarbonyl]chloramphenicol (CHEBI:63766) has functional parent chloramphenicol (CHEBI:17698)
chloramphenicol 3-acetate (CHEBI:16730) has functional parent chloramphenicol (CHEBI:17698)
chloramphenicol palmitate (CHEBI:3605) has functional parent chloramphenicol (CHEBI:17698)
IUPAC Name
2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide
INNs Sources
chloramphenicol WHO MedNet
chloramphénicol WHO MedNet
chloramphenicolum WHO MedNet
cloramfenicol WHO MedNet
Synonyms Sources
(−)-chloramphenicol ChEBI
Chloramphenicol KEGG COMPOUND
CHLORAMPHENICOL PDBeChem
chloramphenicol UniProt
chlornitromycin ChEBI
D-(−)-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide ChemIDplus
D-(−)-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol ChemIDplus
laevomycetinum ChemIDplus
levomicetina ChemIDplus
levomycetin ChemIDplus
Brand Names Sources
Amphicol KEGG DRUG
Chloramex ChemIDplus
Chlorocid ChemIDplus
Chlorocol ChemIDplus
Chloromycetin ChemIDplus
Econochlor KEGG DRUG
Fenicol ChemIDplus
Globenicol ChemIDplus
Halomycetin ChemIDplus
Oleomycetin ChemIDplus
Sificetina ChemIDplus
Manual Xrefs Databases
1835 VSDB
5744 ChemSpider
589 DrugCentral
C00918 KEGG COMPOUND
chloramphenicol Alan Wood's Pesticides
Chloramphenicol Wikipedia
CHLORAMPHENICOL MetaCyc
CLM PDBeChem
D00104 KEGG DRUG
DB00446 DrugBank
GB795131 Patent
GB796901 Patent
HMDB0014589 HMDB
LSM-5256 LINCS
US2483871 Patent
US2483884 Patent
US2483892 Patent
US2839577 Patent
View more database links
Registry Numbers Types Sources
2225532 Beilstein Registry Number Beilstein
56-75-7 CAS Registry Number NIST Chemistry WebBook
56-75-7 CAS Registry Number ChemIDplus
Citations
Berlina AN, Taranova NA, Zherdev AV, Vengerov YY, Dzantiev BB (2013)
Quantum dot-based lateral flow immunoassay for detection of chloramphenicol in milk.
Analytical and bioanalytical chemistry 405, 4997-5000 [PubMed:23494278]
[show Abstract]
Livingston RJ, Butterworth JW, Belt P (2013)
Reaction or infection: topical chloramphenicol treatment.
Annals of the Royal College of Surgeons of England 95, e20-1 [PubMed:23317719]
[show Abstract]
Leston S, Nunes M, Viegas I, Ramos F, Pardal MÂ (2013)
The effects of chloramphenicol on Ulva lactuca.
Chemosphere 91, 552-557 [PubMed:23395526]
[show Abstract]
Tao X, Jiang H, Yu X, Zhu J, Wang X, Wang Z, Niu L, Wu X, Shen J (2013)
An ultrasensitive chemiluminescence immunoassay of chloramphenicol based on gold nanoparticles and magnetic beads.
Drug testing and analysis 5, 346-352 [PubMed:23512826]
[show Abstract]
Houtkooper RH, Mouchiroud L, Ryu D, Moullan N, Katsyuba E, Knott G, Williams RW, Auwerx J (2013)
Mitonuclear protein imbalance as a conserved longevity mechanism.
Nature 497, 451-457 [PubMed:23698443]
[show Abstract]
Adebusuyi A, Foght J (2013)
Physico-chemical factors affect chloramphenicol efflux and EmhABC efflux pump expression in Pseudomonas fluorescens cLP6a.
Research in microbiology 164, 172-180 [PubMed:23142491]
[show Abstract]
Hafner V, Albermann N, Haefeli WE, Ebinger F (2008)
Inhibition of voriconazole metabolism by chloramphenicol in an adolescent with central nervous system aspergillosis.
Antimicrobial agents and chemotherapy 52, 4172-4174 [PubMed:18794387]
[show Abstract]
Yuan ZR, Shi Y (2008)
Chloramphenicol induces abnormal differentiation and inhibits apoptosis in activated T cells.
Cancer research 68, 4875-4881 [PubMed:18559535]
[show Abstract]
Monari M, Foschi J, Cortesi P, Rosmini R, Cattani O, Serrazanetti GP (2008)
Chloramphenicol influence on antioxidant enzymes with preliminary approach on microsomal CYP1A immunopositive-protein in Chamelea gallina.
Chemosphere 73, 272-280 [PubMed:18657290]
[show Abstract]
Chatzitakis A, Berberidou C, Paspaltsis I, Kyriakou G, Sklaviadis T, Poulios I (2008)
Photocatalytic degradation and drug activity reduction of Chloramphenicol.
Water research 42, 386-394 [PubMed:17692887]
[show Abstract]
Wesongah JO, Murilla GA, Guantai AN, Elliot C, Fodey T, Cannavan A (2007)
A competitive enzyme-linked immunosorbent assay for determination of chloramphenicol.
Journal of veterinary pharmacology and therapeutics 30, 68-73 [PubMed:17217404]
[show Abstract]
Eraso AJ, Albesa I (2007)
Eriobotrya japonica counteracts reactive oxygen species and nitric oxide stimulated by chloramphenicol.
The American journal of Chinese medicine 35, 875-885 [PubMed:17963326]
[show Abstract]
Popadic S, Popadic D, Ramic Z, Mostarica Stojkovic M, Trajkovic V, Milinkovic M, Medenica L (2006)
Chloramphenicol induces in vitro growth arrest and apoptosis of human keratinocytes.
Cell biology and toxicology 22, 371-379 [PubMed:16897441]
[show Abstract]
Thompson J, O'Connor M, Mills JA, Dahlberg AE (2002)
The protein synthesis inhibitors, oxazolidinones and chloramphenicol, cause extensive translational inaccuracy in vivo.
Journal of molecular biology 322, 273-279 [PubMed:12217690]
[show Abstract]
Izard T (2001)
Structural basis for chloramphenicol tolerance in Streptomyces venezuelae by chloramphenicol phosphotransferase activity.
Protein science : a publication of the Protein Society 10, 1508-1513 [PubMed:11468347]
[show Abstract]
Strick RA (1983)
Lack of cross-reaction between DNCB and chloramphenicol.
Contact dermatitis 9, 484-487 [PubMed:6653106]
[show Abstract]
Powell DA, Nahata MC (1982)
Chloramphenicol: new perspectives on an old drug.
Drug intelligence & clinical pharmacy 16, 295-300 [PubMed:7040026]
[show Abstract]
Eriksen K (1978)
Cross allergy between paranitro compounds with special reference to DNCB and chloramphenicol.
Contact dermatitis 4, 29-32 [PubMed:657786]
[show Abstract]
Yang NS, Scandalios JG (1977)
Effects of cycloheximide and chloramphenicol on the synthesis of polypeptides found in three subcellular fractions of maize scutellum.
Plant physiology 59, 1067-1071 [PubMed:16659995]
[show Abstract]
Last Modified
23 September 2021