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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014589
Secondary Accession Numbers
  • HMDB14589
Metabolite Identification
Common NameChloramphenicol
DescriptionChloramphenicol, also known as chloromycetin or chloramex, 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. Chloramphenicol is a drug which is used 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. Drug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Chloramphenicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Chloramphenicol exists in all living organisms, ranging from bacteria to humans. An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. In humans, chloramphenicol is involved in chloramphenicol action pathway. Chloramphenicol is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. Chloramphenicol targets the large 39S subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic.
Structure
Data?1582753196
Synonyms
ValueSource
ChloramexChEBI
ChloramphenicolumChEBI
ChlornitromycinChEBI
ChlorocidChEBI
ChlorocolChEBI
ChloromycetinChEBI
CloramfenicolChEBI
D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenylethyl)acetamideChEBI
D-(-)-Threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediolChEBI
FenicolChEBI
GlobenicolChEBI
HalomycetinChEBI
LaevomycetinumChEBI
LevomicetinaChEBI
LevomycetinChEBI
OleomycetinChEBI
SificetinaChEBI
CPKegg
AmphicolKegg
EconochlorKegg
D-(-)-2,2-Dichloro-N-(b-hydroxy-a-(hydroxymethyl)-p-nitrophenylethyl)acetamideGenerator
D-(-)-2,2-Dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamideGenerator
CAFHMDB
CAPHMDB
ChloramfenikolHMDB
ChloramphenicoleHMDB
ChloroamphenicolHMDB
CloroamfenicoloHMDB
D-ChloramphenicolHMDB
DetreomycinHMDB
KloramfenikolHMDB
CloranfenicolHMDB
OphthochlorHMDB
SyntomycinHMDB
AmphenicolsMeSH
AmphenicolMeSH
Chemical FormulaC11H12Cl2N2O5
Average Molecular Weight323.129
Monoisotopic Molecular Weight322.012326918
IUPAC Name2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Traditional Namechloramphenicol
CAS Registry Number56-75-7
SMILES
OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
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
InChI KeyWIIZWVCIJKGZOK-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
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.46 g/LNot Available
LogP0.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+164.42830932474
DeepCCS[M-H]-162.0730932474
DeepCCS[M-2H]-194.95530932474
DeepCCS[M+Na]+170.52130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChloramphenicolOC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O3663.6Standard polar33892256
ChloramphenicolOC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O2540.0Standard non polar33892256
ChloramphenicolOC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O2555.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chloramphenicol,1TMS,isomer #1C[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C([N+](=O)[O-])C=C12458.2Semi standard non polar33892256
Chloramphenicol,1TMS,isomer #2C[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)NC(=O)C(Cl)Cl2442.1Semi standard non polar33892256
Chloramphenicol,1TMS,isomer #3C[Si](C)(C)N(C(=O)C(Cl)Cl)[C@H](CO)[C@H](O)C1=CC=C([N+](=O)[O-])C=C12480.0Semi standard non polar33892256
Chloramphenicol,2TMS,isomer #1C[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C12429.8Semi standard non polar33892256
Chloramphenicol,2TMS,isomer #2C[Si](C)(C)OC[C@H]([C@H](O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C2465.8Semi standard non polar33892256
Chloramphenicol,2TMS,isomer #3C[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)N(C(=O)C(Cl)Cl)[Si](C)(C)C2500.3Semi standard non polar33892256
Chloramphenicol,3TMS,isomer #1C[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C2528.1Semi standard non polar33892256
Chloramphenicol,3TMS,isomer #1C[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C2503.2Standard non polar33892256
Chloramphenicol,3TMS,isomer #1C[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C2922.8Standard polar33892256
Chloramphenicol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C([N+](=O)[O-])C=C12734.8Semi standard non polar33892256
Chloramphenicol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)NC(=O)C(Cl)Cl2724.8Semi standard non polar33892256
Chloramphenicol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)C(Cl)Cl)[C@H](CO)[C@H](O)C1=CC=C([N+](=O)[O-])C=C12804.7Semi standard non polar33892256
Chloramphenicol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C12983.6Semi standard non polar33892256
Chloramphenicol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]([C@H](O)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C3040.7Semi standard non polar33892256
Chloramphenicol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](C1=CC=C([N+](=O)[O-])C=C1)[C@@H](CO)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C3056.9Semi standard non polar33892256
Chloramphenicol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C3288.7Semi standard non polar33892256
Chloramphenicol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C3139.3Standard non polar33892256
Chloramphenicol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]([C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1)N(C(=O)C(Cl)Cl)[Si](C)(C)C(C)(C)C3136.8Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00446 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00446 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00446
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5744
KEGG Compound IDC00918
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChloramphenicol
METLIN IDNot Available
PubChem Compound5959
PDB IDCLM
ChEBI ID17698
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16039333 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]