Molecule Details
| InChIKey | WIIZWVCIJKGZOK-RKDXNWHRSA-N |
|---|---|
| Compound Name | Chloramphenicol |
| Canonical SMILES | O=C(N[C@H](CO)[C@H](O)c1ccc([N+](=O)[O-])cc1)C(Cl)Cl |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 55 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.37 |
| Source | ChEMBL |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00446 |
|---|---|
| Drug Name | Chloramphenicol |
| CAS Number | 56-75-7 |
| Groups | approved vet_approved withdrawn |
| ATC Codes | D06AX02 S02AA01 D10AF03 S01AA01 G01AA05 J01BA01 S03AA08 |
| Description | An antibiotic first isolated from cultures of _Streptomyces venezuelae_ 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. (Fr... |
Categories: Alcohols Amphenicols Anti-Acne Preparations Anti-Acne Preparations for Topical Use Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antibiotics for Topical Use Antiinfectives for Systemic Use Antiinfectives for Treatment of Acne Benzene Derivatives Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (strong) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Dermatologicals Enzyme Inhibitors Genito Urinary System and Sex Hormones Glycols Gynecological Antiinfectives and Antiseptics Immunosuppressive Agents Myelosuppressive Agents Nitro Compounds Nitrobenzenes OAT1/SLC22A6 inhibitors Ophthalmological and Otological Preparations Ophthalmologicals Otologicals Propylene Glycols Protein Synthesis Inhibitors Sensory Organs
Cross-references: BindingDB: 23447 ChEBI: 17698 CHEMBL130 ChemSpider: 5744 Drugs Product Database (DPD): 16112 C00918 D00104 PDB: CLM PharmGKB: PA448927 PubChem:5959 PubChem:46505318 RxCUI: 2348 Therapeutic Targets Database: DAP001356 Wikipedia: Chloramphenicol ZINC: ZINC000000113382
Target Activities (55)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P02358 | rpsF | Escherichia coli (strain K12) | Pathogen | PF01250 | 6.4 | IC50 | ChEMBL |
| P02359 | rpsG | Escherichia coli (strain K12) | Pathogen | PF00177 | 6.4 | IC50 | ChEMBL |
| P02413 | rplO | Escherichia coli (strain K12) | Pathogen | PF00828 | 6.4 | IC50 | ChEMBL |
| P0A7J3 | rplJ | Escherichia coli (strain K12) | Pathogen | PF00466 | 6.4 | IC50 | ChEMBL |
| P0A7J7 | rplK | Escherichia coli (strain K12) | Pathogen | PF00298 PF03946 | 6.4 | IC50 | ChEMBL |
| P0A7K2 | rplL | Escherichia coli (strain K12) | Pathogen | PF00542 PF16320 | 6.4 | IC50 | ChEMBL |
| P0A7K6 | rplS | Escherichia coli (strain K12) | Pathogen | PF01245 | 6.4 | IC50 | ChEMBL |
| P0A7L0 | rplA | Escherichia coli (strain K12) | Pathogen | PF00687 | 6.4 | IC50 | ChEMBL |
| P0A7L3 | rplT | Escherichia coli (strain K12) | Pathogen | PF00453 | 6.4 | IC50 | ChEMBL |
| P0A7L8 | rpmA | Escherichia coli (strain K12) | Pathogen | PF01016 | 6.4 | IC50 | ChEMBL |
| P0A7M2 | rpmB | Escherichia coli (strain K12) | Pathogen | PF00830 | 6.4 | IC50 | ChEMBL |
| P0A7M6 | rpmC | Escherichia coli (strain K12) | Pathogen | PF00831 | 6.4 | IC50 | ChEMBL |
| P0A7M9 | rpmE | Escherichia coli (strain K12) | Pathogen | PF01197 | 6.4 | IC50 | ChEMBL |
| P0A7N1 | ykgM | Escherichia coli (strain K12) | Pathogen | PF01197 | 6.4 | IC50 | ChEMBL |
| P0A7N4 | rpmF | Escherichia coli (strain K12) | Pathogen | PF01783 | 6.4 | IC50 | ChEMBL |
| P0A7N9 | rpmG | Escherichia coli (strain K12) | Pathogen | PF00471 | 6.4 | IC50 | ChEMBL |
| P0A7P5 | rpmH | Escherichia coli (strain K12) | Pathogen | PF00468 | 6.4 | IC50 | ChEMBL |
| P0A7Q1 | rpmI | Escherichia coli (strain K12) | Pathogen | PF01632 | 6.4 | IC50 | ChEMBL |
| P0A7Q6 | rpmJ | Escherichia coli (strain K12) | Pathogen | PF00444 | 6.4 | IC50 | ChEMBL |
| P0A7R5 | rpsJ | Escherichia coli (strain K12) | Pathogen | PF00338 | 6.4 | IC50 | ChEMBL |
| P0A7R9 | rpsK | Escherichia coli (strain K12) | Pathogen | PF00411 | 6.4 | IC50 | ChEMBL |
| P0A7S3 | rpsL | Escherichia coli (strain K12) | Pathogen | PF00164 | 6.4 | IC50 | ChEMBL |
| P0A7S9 | rpsM | Escherichia coli (strain K12) | Pathogen | PF00416 | 6.4 | IC50 | ChEMBL |
| P0A7T3 | rpsP | Escherichia coli (strain K12) | Pathogen | PF00886 | 6.4 | IC50 | ChEMBL |
| P0A7T7 | rpsR | Escherichia coli (strain K12) | Pathogen | PF01084 | 6.4 | IC50 | ChEMBL |
| P0A7U3 | rpsS | Escherichia coli (strain K12) | Pathogen | PF00203 | 6.4 | IC50 | ChEMBL |
| P0A7U7 | rpsT | Escherichia coli (strain K12) | Pathogen | PF01649 | 6.4 | IC50 | ChEMBL |
| P0A7V0 | rpsB | Escherichia coli (strain K12) | Pathogen | PF00318 | 6.4 | IC50 | ChEMBL |
| P0A7V3 | rpsC | Escherichia coli (strain K12) | Pathogen | PF07650 PF00189 | 6.4 | IC50 | ChEMBL |
| P0A7V8 | rpsD | Escherichia coli (strain K12) | Pathogen | PF00163 PF01479 | 6.4 | IC50 | ChEMBL |
| P0A7W1 | rpsE | Escherichia coli (strain K12) | Pathogen | PF00333 PF03719 | 6.4 | IC50 | ChEMBL |
| P0A7W7 | rpsH | Escherichia coli (strain K12) | Pathogen | PF00410 | 6.4 | IC50 | ChEMBL |
| P0A7X3 | rpsI | Escherichia coli (strain K12) | Pathogen | PF00380 | 6.4 | IC50 | ChEMBL |
| P0AA10 | rplM | Escherichia coli (strain K12) | Pathogen | PF00572 | 6.4 | IC50 | ChEMBL |
| P0ADY3 | rplN | Escherichia coli (strain K12) | Pathogen | PF00238 | 6.4 | IC50 | ChEMBL |
| P0ADY7 | rplP | Escherichia coli (strain K12) | Pathogen | PF00252 | 6.4 | IC50 | ChEMBL |
| P0ADZ0 | rplW | Escherichia coli (strain K12) | Pathogen | PF00276 | 6.4 | IC50 | ChEMBL |
| P0ADZ4 | rpsO | Escherichia coli (strain K12) | Pathogen | PF00312 | 6.4 | IC50 | ChEMBL |
| P0AG44 | rplQ | Escherichia coli (strain K12) | Pathogen | PF01196 | 6.4 | IC50 | ChEMBL |
| P0AG48 | rplU | Escherichia coli (strain K12) | Pathogen | PF00829 | 6.4 | IC50 | ChEMBL |
| P0AG51 | rpmD | Escherichia coli (strain K12) | Pathogen | PF00327 | 6.4 | IC50 | ChEMBL |
| P0AG55 | rplF | Escherichia coli (strain K12) | Pathogen | PF00347 | 6.4 | IC50 | ChEMBL |
| P0AG59 | rpsN | Escherichia coli (strain K12) | Pathogen | PF00253 | 6.4 | IC50 | ChEMBL |
| P0AG63 | rpsQ | Escherichia coli (strain K12) | Pathogen | PF00366 | 6.4 | IC50 | ChEMBL |
| P0AG67 | rpsA | Escherichia coli (strain K12) | Pathogen | PF00575 | 6.4 | IC50 | ChEMBL |
| P0C018 | rplR | Escherichia coli (strain K12) | Pathogen | PF00861 | 6.4 | IC50 | ChEMBL |
| P60422 | rplB | Escherichia coli (strain K12) | Pathogen | PF03947 PF00181 | 6.4 | IC50 | ChEMBL |
| P60438 | rplC | Escherichia coli (strain K12) | Pathogen | PF00297 | 6.4 | IC50 | ChEMBL |
| P60624 | rplX | Escherichia coli (strain K12) | Pathogen | PF00467 PF17136 | 6.4 | IC50 | ChEMBL |
| P60723 | rplD | Escherichia coli (strain K12) | Pathogen | PF00573 | 6.4 | IC50 | ChEMBL |
| P61175 | rplV | Escherichia coli (strain K12) | Pathogen | PF00237 | 6.4 | IC50 | ChEMBL |
| P62399 | rplE | Escherichia coli (strain K12) | Pathogen | PF00281 PF00673 | 6.4 | IC50 | ChEMBL |
| P68679 | rpsU | Escherichia coli (strain K12) | Pathogen | PF01165 | 6.4 | IC50 | ChEMBL |
| P68919 | rplY | Escherichia coli (strain K12) | Pathogen | PF01386 | 6.4 | IC50 | ChEMBL |
| Q2EEQ2 | ykgO | Escherichia coli (strain K12) | Pathogen | PF00444 | 6.4 | IC50 | ChEMBL |
DrugBank Target Actions (11)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | inhibitor | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | inhibitor | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | inhibitor | enzymes |
| P00484 | P00484 | Chloramphenicol acetyltransferase 3 | substrate | enzymes |
| P26841 | P26841 | Chloramphenicol acetyltransferase | substrate | enzymes |
| Q56148 | Q56148 | Chloramphenicol 3-O phosphotransferase | substrate | enzymes |
| P24093 | P24093 | Dr hemagglutinin structural subunit | antagonist | targets |
| P0ADY7 | rplP | Large ribosomal subunit protein uL16 | inhibitor | targets |
| P08174 | P08174 | Complement decay-accelerating factor | other | targets |
| Q4U2R8 | SLC22A6 | Solute carrier family 22 member 6 | inhibitor | transporters |