Chloramphenicol (T3D3954)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2014-08-28 20:38:55 UTC
Update Date2014-12-24 20:26:34 UTC
Accession NumberT3D3954
Identification
Common NameChloramphenicol
ClassSmall Molecule
DescriptionAn 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)
Compound Type
  • Anti-Bacterial Agent
  • Drug
  • Metabolite
  • Organic Compound
  • Protein Synthesis Inhibitor
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Brochlor
Chloramex
Chloramphenicolum
Chlornitromycin
Chlorocid
Chlorocol
Chloromycetin
Chlorsig
Cloramfenicol
D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-P-nitrophenylethyl)acetamide
D-(-)-threo-1-P-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol
Fenicol
Globenicol
Halomycetin
Laevomycetinum
Levomicetina
Levomycetin
Oleomycetin
Sificetina
Chemical FormulaC11H12Cl2N2O5
Average Molecular Mass323.129 g/mol
Monoisotopic Mass322.012 g/mol
CAS Registry Number56-75-7
IUPAC Name2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Traditional Namechloramphenicol
SMILES[H][C@](CO)(N=C(O)C(Cl)Cl)[C@]([H])(O)C1=CC=C(C=C1)N(=O)=O
InChI IdentifierInChI=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
InChI KeyInChIKey=WIIZWVCIJKGZOK-RKDXNWHRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • C-nitro compound
  • Secondary alcohol
  • Organic nitro compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Aromatic alcohol
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Alkyl halide
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Alcohol
  • Alkyl chloride
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Bone Marrow
  • Heart
  • Liver
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point171°C
Boiling PointNot Available
Solubility2500 mg/L (at 25°C)
LogP1.14
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP1.15ALOGPS
logP0.88ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)7.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area115.38 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.2 m³·mol⁻¹ChemAxon
Polarizability28.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-2ba6754ba027027454d12017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-3911100000-5438beab478c45792ddb2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0920000000-96bfb1c31d89e3f10caf2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0kmi-0945000000-40a09f3f9528bd6698232017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-64dbb16119292f4410e22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-5c8fbcad8e93fa9f29062017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0uk9-1900000000-4c6518583a7488591aa32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-1900000000-00574ed667d64b4a45e92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-1900000000-d4ac63e9260ab31ac6b12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zml-0933000000-4ae209b29cb52d4e38442017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-056r-0933000000-74ff5ec451e56526d4252017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4l-0590000000-90d108018a0f99815fb72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4l-0690000000-161f2afa43298fd3437a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0uk9-0923000000-86308db0ec59b40b15332017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-0094000000-ad8da59124745b38a76f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0390000000-06fcf307f2fdb79741ad2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-1940000000-be07d702045f4d3e05ac2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-1910000000-55a74a828c3c9750ee1c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-2900000000-bf685c17ab79583133ee2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-4900000000-e6f6ccbfffe89c3453652017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0191000000-41f70006e2b4e5f8d8aa2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0109000000-7f19e2214bd804fbb5722016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0289000000-ea9835706b530fa071972016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2910000000-531d8b69053d0c007aeb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-cc647af0a1726c8e11c52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-3915000000-a08bc180ba95289b92972016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4900000000-7ccaa4da01cb96a52d232016-08-03View Spectrum
Toxicity Profile
Route of ExposureRapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.
Mechanism of ToxicityChloramphenicol targets the large 39S subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result chloramphenicol is cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. (6). The likely target of chloramphenicol is the 16S rRNA molecule in the mitochondrial ribosome, which is analogous to the 23S rRNA in bacterial ribosomes.
MetabolismHepatic, with 90% conjugated to inactive glucuronide. Half Life: Half-life in adults with normal hepatic and renal function is 1.5 - 3.5 hours. In patients with impaired renal function half-life is 3 - 4 hours. In patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to 16 years old is 3 - 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.
Toxicity ValuesOral, mouse: LD50 = 1500 mg/kg Oral, rat: LD50 = 2500 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (8)
Uses/SourcesUsed in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.
Minimum Risk LevelNot Available
Health EffectsThe most serious adverse effect associated with chloramphenicol treatment is bone marrow toxicity, which may occur in two distinct forms: 1) bone marrow suppression, which is a direct toxic effect of the drug and is usually reversible, and 2) aplastic anemia, which is idiosyncratic (rare, unpredictable) and generally fatal. Other less serious reactions from chloramphenicol use include fever, rashes, headache, and confusion. Use of intravenous chloramphenicol has also been associated with gray baby syndrome, a phenomenon resulting from newborn infants' inability to metabolize chloramphenicol in the liver via UDP-glucuronyl transferase. Gray baby syndrome is characterized by vomiting, ashen gray color of the skin, limp body tone, hypotension and cyanosis.
SymptomsToxic reactions including fatalities have occurred in the premature and newborn; the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of appearance) abdominal distension with or without emesis, progressive pallid cyanosis, vasomotor collapse frequently accompanied by irregular respiration, and death within a few hours of onset of these symptoms.
TreatmentDrug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Sometimes, phenobarbital (UGT induction) is used.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00446
HMDB IDHMDB14589
PubChem Compound ID298
ChEMBL IDCHEMBL130
ChemSpider ID5744
KEGG IDC00918
UniProt IDNot Available
OMIM ID
ChEBI ID17698
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkChloramphenicol
References
Synthesis Reference

Guang-Zhong Wu, Wanda I. Tormos, “Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates.” U.S. Patent US5352832, issued May, 1992.

MSDST3D3954.pdf
General References
  1. Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [538813 ]
  2. Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [1398851 ]
  3. Pecoul B, Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [1681224 ]
  4. Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [6464136 ]
  5. Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [16039333 ]
  6. McKee EE, Ferguson M, Bentley AT, Marks TA: Inhibition of mammalian mitochondrial protein synthesis by oxazolidinones. Antimicrob Agents Chemother. 2006 Jun;50(6):2042-9. [16723564 ]
  7. Wikipedia. Chloramphenicol. Last updated on 28 August 2014. [Link]
  8. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Complement decay-accelerating factor
General Function:
Virus receptor activity
Specific Function:
This protein recognizes C4b and C3b fragments that condense with cell-surface hydroxyl or amino groups when nascent C4b and C3b are locally generated during C4 and c3 activation. Interaction of daf with cell-associated C4b and C3b polypeptides interferes with their ability to catalyze the conversion of C2 and factor B to enzymatically active C2a and Bb and thereby prevents the formation of C4b2a and C3bBb, the amplification convertases of the complement cascade.(Microbial infection) Acts as a receptor for coxsackievirus A21, coxsackieviruses B1, B3 and B5 (PubMed:9151867). Acts as a receptor for human enterovirus 70 and D68 (Probable) (PubMed:8764022). Acts as a receptor for human echoviruses 6, 7, 11, 12, 20 and 21 (PubMed:7525274).
Gene Name:
CD55
Uniprot ID:
P08174
Molecular Weight:
41399.79 Da
References
  1. Pettigrew D, Anderson KL, Billington J, Cota E, Simpson P, Urvil P, Rabuzin F, Roversi P, Nowicki B, du Merle L, Le Bouguenec C, Matthews S, Lea SM: High resolution studies of the Afa/Dr adhesin DraE and its interaction with chloramphenicol. J Biol Chem. 2004 Nov 5;279(45):46851-7. Epub 2004 Aug 24. [15331605 ]
  2. Korotkova N, Chattopadhyay S, Tabata TA, Beskhlebnaya V, Vigdorovich V, Kaiser BK, Strong RK, Dykhuizen DE, Sokurenko EV, Moseley SL: Selection for functional diversity drives accumulation of point mutations in Dr adhesins of Escherichia coli. Mol Microbiol. 2007 Apr;64(1):180-94. [17376081 ]
Target Details
2. 16S RNA
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Binding9.80 uMNot AvailableNot Available