Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D0X6IU
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| Former ID |
DAP000460
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| Drug Name |
Chloramphenicol
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| Synonyms |
Alficetyn; Ambofen; Amphenicol; Amphicol; Amseclor; Anacetin; Aquamycetin; Austracil; Austracol; Biocetin; Biophenicol; CAF; CLM; Catilan; Chemiceticol; Chemicetin; Chemicetina; Chlomin; Chlomycol; Chloramex; Chloramfenikol; Chloramficin; Chloramfilin; Chloramphenicolum; Chloramsaar; Chlorasol; Chloricol; Chlornitromycin; Chloroamphenicol; Chlorocaps; Chlorocid; Chlorocide; Chlorocol; Chlorofair; Chloromax; Chloromycetin; Chloromycetny; Chloromyxin; Chloronitrin; Chloroptic; Chlorovules; Chlorsig; Cidocetine; Ciplamycetin; Cloramfen; Cloramfenicol; Cloramfenicolo; Cloramficin; Cloramical; Cloramicol; Cloramidina; Cloranfenicol; Cloroamfenicolo; Clorocyn; Cloromisan; Cloromissan; Clorosintex; Comycetin; Cylphenicol; Desphen; Detreomycin; Detreomycine; Dextromycetin; Doctamicina; Duphenicol; Econochlor; Embacetin; Emetren; Enicol; Enteromycetin; Erbaplast; Ertilen; Farmicetina; Fenicol; Globenicol; Glorous; Halomycetin; Hortfenicol; Interomycetine; Intramycetin; Intramyctin; Isicetin; Ismicetina; Isophenicol; Juvamycetin; Kamaver; Kemicetina; Kemicetine; Kloramfenikol; Klorita; Laevomycetinum; Leukamycin; Leukomyan; Leukomycin; Levomicetina; Levomitsetin; Levomycetin; Loromicetina; Loromisan; Loromisin; Mastiphen; Mediamycetine; Medichol; Micloretin; Micochlorine; Micoclorina; Microcetina; Mychel; Mycinol; Myscel; Novochlorocap; Novomycetin; Novophenicol; Oftalent; Oleomycetin; Opclor; Opelor; Ophthochlor; Ophtochlor; Optomycin; Otachron; Otophen; Pantovernil; Paraxin; Pentamycetin; Quemicetina; Rivomycin; Romphenil; Ronfenil; Ronphenil; Septicol; Sificetina; Sintomicetina; Stanomycetin; Synthomycetin; Synthomycetine; Synthomycine; Syntomycin; Tevcocin; Tevcosin; Tifomycin; Tifomycine;Tiromycetin; Treomicetina; Unimycetin; Veticol; Viceton; Ch loramex; Chloramfenikol [Czech]; Chloramphenicol crystalline; Chlormycetin R; Chlorocid S; Chlorocidin C; Chlorocidin C tetran; Chloroject L; Chloromycetny [Polish]; Cloramfenicolo [DCIT]; Cloroamfenicolo [Italian]; F armicetina; Isopto fenicol; Klorocid S; Normimycin V; Sintomicetine R; Sno Phenicol; Vice ton; I 337A; Ak-chlor; Alficetyn (TN); Amphicol (TN); Biomicin (TN); Brochlor (TN); CAF (pharmaceutical); Cedoctine (TN); Chlora-tabs; Chloramex (TN); Chloramphenicol & VRC3375; Chloramphenicolum [INN-Latin]; Chlorbiotic (Veterinary); Chlornitromycin (TN); Chloro-25 vetag; Chloromycetin (TN); Chlorsig (TN); Cloramfenicol [INN-Spanish]; D-Chloramphenicol; Dispersadron C (TN); Econochlor (TN); Elase-Chloromycetin; Fenicol (TN); Golden Eye (TN); Isoptophenicol (TN); Kemicetine (TN); Laevomycetin (TN); Medicom (TN); Mychel-Vet; Nevimycin (TN); Oftan Chlora (TN); Optrex Infected Eyes (TN); Orchadexoline (TN); Phenicol (TN); Renicol (TN); Silmycetin (TN); Sno-Phenicol; Synthomycine (TN); Tea-Cetin; Tega-Cetin; Tifomycine (TN); U-6062; Vernacetin (TN); Veticol (TN); C.A.F; CHLOROPTIC S.O.P; Chloramphenicol [INN:BAN:JAN]; Chloromycetin® D-threo-Chloramphenicol; Alficetyn, Chlornitromycin, Chloromycetin, Chloramphenicol; Chloramphenicol (JP15/USP/INN); Chloroptic S.O.P.; D(-)-threo-Chloramphenicol; D-(-)-Chloramphenicol; D-(-)-threo-Chloramphenicol; D(-)-threo-2-dichloroacetamido-1-p-nitrophen yl-propanediol; D(-)-threo-2-dichloroacetamido-1-p-nitrophenyl-propanediol
Click to Show/Hide
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| Drug Type |
Small molecular drug
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| Indication | Bacterial infection [ICD-11: 1A00-1C4Z; ICD-10: A00-B99] | Approved | [1] | |
| Therapeutic Class |
Antibiotics
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| Company |
Aventis Pharmaceuticals Inc.
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| Structure |
 |
Download2D MOL |
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| Formula |
C11H12Cl2N2O5
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| Canonical SMILES |
C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
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| 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
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| InChIKey |
WIIZWVCIJKGZOK-RKDXNWHRSA-N
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| CAS Number |
CAS 56-75-7
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| PubChem Compound ID | ||||
| PubChem Substance ID |
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
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| ChEBI ID |
CHEBI:17698
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| ADReCS Drug ID | BADD_D00430 | |||
| SuperDrug ATC ID |
D06AX02; D10AF03; G01AA05; J01BA01; S01AA01; S02AA01; S03AA08
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| SuperDrug CAS ID |
cas=000056757
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
|
Studied Microbe: Escherichia coli
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[2] | |||
| Hierarchy | ||||
| Metabolic Effect | Increase toxicity | |||
| Description | Chloramphenicol can be metabolized by Escherichia coli, which results in the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [3], [4] | |||
| Metabolic Reaction | Amine formation and hydrolysis of an amide linkage | |||
| Resulting Metabolite | P-aminophenyl-2-amino-1,3-propanediol | |||
| Metabolic Effect | Increase activity; Increase side effect | |||
| Description | Chloramphenicol can be metabolized to P-aminophenyl-2-amino-1,3-propanediol by gut microbiota through amine formation and hydrolysis of an amide linkage, which results in the increase of drug's activity and side effect. | |||
| Studied Microbe: Gut microbiota unspecific | [5], [6] | |||
| Metabolic Reaction | Nitroreduction | |||
| Resulting Metabolite | P-aminophenyl-2-amino-1,3-propanediol | |||
| Metabolic Effect | Increase toxicity (bone marrow toxicity) | |||
| Description | Chloramphenicol can be metabolized to P-aminophenyl-2-amino-1,3-propanediol by gut microbiota through nitroreduction, which results in the increase of the drug's toxicity (bone marrow toxicity). | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides caccae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides caccae was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bacteroides fragilis enterotoxigenic
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides fragilis enterotoxigenic was decreased by Chloramphenicol (adjusted p-values: 5.87E-06). | |||
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Studied Microbe: Bacteroides fragilis nontoxigenic
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides fragilis nontoxigenic was decreased by Chloramphenicol (adjusted p-values: 5.99E-06). | |||
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Studied Microbe: Bacteroides ovatus
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides ovatus was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bacteroides thetaiotaomicron
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides thetaiotaomicron was decreased by Chloramphenicol (adjusted p-values: 9.66E-06). | |||
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Studied Microbe: Bacteroides uniformis
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides uniformis was decreased by Chloramphenicol (adjusted p-values: 7.03E-07). | |||
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Studied Microbe: Bacteroides vulgatus
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides vulgatus was decreased by Chloramphenicol (adjusted p-values: 1.95E-06). | |||
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Studied Microbe: Bacteroides xylanisolvens
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides xylanisolvens was decreased by Chloramphenicol (adjusted p-values: 4.93E-07). | |||
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Studied Microbe: Odoribacter splanchnicus
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Odoribacter splanchnicus was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Parabacteroides distasonis
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides distasonis was decreased by Chloramphenicol (adjusted p-values: 2.74E-07). | |||
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Studied Microbe: Parabacteroides merdae
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides merdae was decreased by Chloramphenicol (adjusted p-values: 4.93E-07). | |||
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Studied Microbe: Prevotella copri
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Prevotella copri was decreased by Chloramphenicol (adjusted p-values: 3.29E-05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium adolescentis
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium adolescentis was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bifidobacterium longum
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium longum was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Collinsella aerofaciens
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Chloramphenicol (adjusted p-values: 2.73E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Eggerthella lenta
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eggerthella lenta was decreased by Chloramphenicol (adjusted p-values: 1.56E-05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli ED1a
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Escherichia coli ED1a was decreased by Chloramphenicol (adjusted p-values: 9.88E-06). | |||
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Studied Microbe: Escherichia coli IAI1
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Escherichia coli IAI1 was decreased by Chloramphenicol (adjusted p-values: 4.93E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
|
Studied Microbe: Erysipelatoclostridium ramosum
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Erysipelatoclostridium ramosum was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia obeum
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Blautia obeum was decreased by Chloramphenicol (adjusted p-values: 3.02E-06). | |||
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Studied Microbe: Clostridioides difficile
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridioides difficile was decreased by Chloramphenicol (adjusted p-values: 3.06E-05). | |||
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Studied Microbe: Clostridium perfringens
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridium perfringens was decreased by Chloramphenicol (adjusted p-values: 6.57E-07). | |||
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Studied Microbe: Coprococcus comes
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Dorea formicigenerans
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Dorea formicigenerans was decreased by Chloramphenicol (adjusted p-values: 1.96E-05). | |||
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Studied Microbe: Enterocloster bolteae
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Enterocloster bolteae was decreased by Chloramphenicol (adjusted p-values: 1.03E-05). | |||
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Studied Microbe: Eubacterium eligens
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium eligens was decreased by Chloramphenicol (adjusted p-values: 9.91E-06). | |||
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Studied Microbe: Eubacterium rectale
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium rectale was decreased by Chloramphenicol (adjusted p-values: 1.71E-04). | |||
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Studied Microbe: Lacrimispora saccharolytica
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lacrimispora saccharolytica was decreased by Chloramphenicol (adjusted p-values: 3.02E-07). | |||
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Studied Microbe: Roseburia hominis
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia hominis was decreased by Chloramphenicol (adjusted p-values: 1.99E-05). | |||
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Studied Microbe: Roseburia intestinalis
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by Chloramphenicol (adjusted p-values: 1.84E-04). | |||
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Studied Microbe: Ruminococcus bromii
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus bromii was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Ruminococcus gnavus
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus gnavus was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Ruminococcus torques
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus torques was decreased by Chloramphenicol (adjusted p-values: 7.77E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactobacillus paracasei
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lactobacillus paracasei was decreased by Chloramphenicol (adjusted p-values: 5.51E-07). | |||
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Studied Microbe: Streptococcus parasanguinis
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus parasanguinis was decreased by Chloramphenicol (adjusted p-values: 8.55E-07). | |||
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Studied Microbe: Streptococcus salivarius
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus salivarius was decreased by Chloramphenicol (adjusted p-values: 5.51E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Veillonellales | ||||
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Studied Microbe: Veillonella parvula
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Veillonella parvula was decreased by Chloramphenicol (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Verrucomicrobiales | ||||
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Studied Microbe: Akkermansia muciniphila
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Akkermansia muciniphila was decreased by Chloramphenicol (adjusted p-values: 5.99E-07). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Bacterial 23S ribosomal RNA (Bact 23S rRNA) | Target Info | Binder | [8] |
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92. | |||
| REF 2 | Pharmacomicrobiomics: The Holy Grail to Variability in Drug Response?. Clin Pharmacol Ther. 2019 Aug;106(2):317-328. | |||
| REF 3 | Cometabolism of microbes and host: implications for drug metabolism and drug-induced toxicity. Clin Pharmacol Ther. 2013 Nov;94(5):574-81. | |||
| REF 4 | The metabolic effect of gut microbiota on drugs. Drug Metab Rev. 2020 Feb;52(1):139-156. | |||
| REF 5 | Gut microbiome interactions with drug metabolism, efficacy, and toxicity. Transl Res. 2017 Jan;179:204-222. | |||
| REF 6 | Predicting and Understanding the Human Microbiome's Impact on Pharmacology. Trends Pharmacol Sci. 2019 Jul;40(7):495-505. | |||
| REF 7 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 8 | Inhibition of peptide bond formation by pleuromutilins: the structure of the 50S ribosomal subunit from Deinococcus radiodurans in complex with tiamulin. Mol Microbiol. 2004 Dec;54(5):1287-94. | |||
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