Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0298)
Drug Name
Chloramphenicol
Synonyms
Chloramex; Chloramficin; Chloramfilin; Chlornitromycin; Chloroamphenicol; Chlorocid; Chlorocol; Chloromycetin; Chloronitrin; Ciplamycetin; Cloramicol; Comycetin; Alficetyn; Amphenicol; Aquamycetin; D-Chloramphenicol; Detreomycin; Detreomycine; Dextromycetin; Enteromycetin; Fenicol; Globenicol; Halomycetin; Intramycetin; Isophenicol; Juvamycetin; Kemicetina; Laevomycetinum; Leukomycin; Levomicetina; Levomitsetin; Levomycetin; Mediamycetine; Micochlorine; Novophenicol; Oleomycetin; Ophthochlor; Sificetina; Stanomycetin; chloramphenicol; 56-75-7
Indication Conjunctivitis [ICD11: 9A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 323.13 Topological Polar Surface Area 115
Heavy Atom Count 20 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5959
PubChem SID
4172 ; 69616 ; 584412 ; 608885 ; 823928 ; 830913 ; 830918 ; 929553 ; 3139682 ; 7847172 ; 7886640 ; 7978916 ; 8137815 ; 8144048 ; 8149244 ; 8153702 ; 10527641 ; 11335719 ; 11360958 ; 11407013 ; 11461930 ; 14801512 ; 15000217 ; 17389985 ; 24853926 ; 24867881 ; 24892250 ; 24892278 ; 24892441 ; 24892448 ; 24892989 ; 26703879 ; 26718309 ; 26718473 ; 26718874 ; 26752873 ; 26758463 ; 29224982 ; 46505318 ; 47193729 ; 47588966 ; 47662251 ; 47662252 ; 48035081 ; 48259200 ; 48413399 ; 48415752 ; 48424947 ; 48464250 ; 49698995
ChEBI ID
ChEBI:17698
CAS Number
56-75-7
TTD Drug ID
D0X6IU
Formula
C11H12Cl2N2O5
Canonical SMILES
C1=CC(=CC=C1C(C(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
InChIKey
WIIZWVCIJKGZOK-RKDXNWHRSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
D-threo-2-amino-1-(p-nitrophenyl)-1,3-propanediol DM001815
69745
Unclear 1 [5]
Desmethylcerivastatin DM001795
71315726
Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000624 Chloramphenicol Desmethylcerivastatin Unclear CYP3A4 ... [5]
MR000625 Chloramphenicol D-threo-2-amino-1-(p-nitrophenyl)-1,3-propanediol Unclear CYP3A4 ... [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Chloramphenicolase (chlR) DME1028 Escherichia coli
A0A5M4B0P0_9BACT
2.3.1.28
[2]
Chloramphenicolase (chlR) DME1030 Bacillus pumilus
A0A5M4B0P0_9BACT
2.3.1.28
[2]
Chloramphenicolase (chlR) DME1031 Proteus penneri
A0A5M4B0P0_9BACT
2.3.1.28
[2]
Glycerol-3-phosphate dehydrogenase (gpsA) DME1029 Erysipelothrix rhusiopathiae
A0A411LCN0_ERYRH
1.1.1.94
[3] , [4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1279 Methanobrevibacter oralis Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1280 Methanobrevibacter smithii Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1281 Methanomassiliicoccus luminyensis Not Available Not Available [7]
⏷ Show the Full List of 9  DME(s)
References
1 Chloramphenicol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The bacterial degradation of chloramphenico. Lancet. 1967 Jun 10;1(7502):1259-60.
3 Porcine beta-defensin 2 displays broad antimicrobial activity against pathogenic intestinal bacteria. Mol Immunol. 2008 Jan;45(2):386-94.
4 Dehydrogenase activity of chlornitromycin-resistant variants of Erysipelothrix rhusiopathiae. Izv Mikrobiol Inst (Sofiia). 1969;20:257-62.
5 Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in human liver microsomes. Antimicrob Agents Chemother. 2003 Nov;47(11):3464-9.
6 The effect of low-pressure carbonation on the heat inactivation of Escherichia coli. Biosci Biotechnol Biochem. 2011;75(10):1945-50.
7 The antimicrobial resistance pattern of cultured human methanogens reflects the unique phylogenetic position of archaea. J Antimicrob Chemother. 2011 Sep;66(9):2038-44.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.