Molecule Details
| InChIKey | MQTOSJVFKKJCRP-BICOPXKESA-N |
|---|---|
| Compound Name | Azithromycin |
| Canonical SMILES | CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 55 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.52 |
| Source | ChEMBL |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00207 |
|---|---|
| Drug Name | Azithromycin |
| CAS Number | 83905-01-5 |
| Groups | approved investigational |
| ATC Codes | J01RA07 S01AA26 J01FA10 J01RA16 |
| Description | Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration [A174172]. It was initially approved by the FDA in 1991 [A174175]. It is primarily used for the treatment of respiratory, enteric and genitourinary infections and may be used instead o... |
Categories: Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antiinfectives for Systemic Use Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Experimental Unapproved Treatments for COVID-19 Lactones Macrolide Antimicrobial Macrolides Macrolides, Lincosamides and Streptogramins Moderate Risk QTc-Prolonging Agents Ophthalmologicals P-glycoprotein inhibitors P-glycoprotein substrates Photosensitizing Agents Polyketides QTc Prolonging Agents
Cross-references: BindingDB: 50373918 ChEBI: 2955 CHEMBL529 ChemSpider: 10482163 Drugs Product Database (DPD): 424 C06838 PDB: ZIT PharmGKB: PA448519 PubChem:447043 PubChem:46507743 RxCUI: 1299904 Therapeutic Targets Database: DNC001539 Wikipedia: Azithromycin ZINC: ZINC000085537026
Target Activities (55)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P02358 | rpsF | Escherichia coli (strain K12) | Pathogen | PF01250 | 6.5 | IC50 | ChEMBL |
| P02359 | rpsG | Escherichia coli (strain K12) | Pathogen | PF00177 | 6.5 | IC50 | ChEMBL |
| P02413 | rplO | Escherichia coli (strain K12) | Pathogen | PF00828 | 6.5 | IC50 | ChEMBL |
| P0A7J3 | rplJ | Escherichia coli (strain K12) | Pathogen | PF00466 | 6.5 | IC50 | ChEMBL |
| P0A7J7 | rplK | Escherichia coli (strain K12) | Pathogen | PF00298 PF03946 | 6.5 | IC50 | ChEMBL |
| P0A7K2 | rplL | Escherichia coli (strain K12) | Pathogen | PF00542 PF16320 | 6.5 | IC50 | ChEMBL |
| P0A7K6 | rplS | Escherichia coli (strain K12) | Pathogen | PF01245 | 6.5 | IC50 | ChEMBL |
| P0A7L0 | rplA | Escherichia coli (strain K12) | Pathogen | PF00687 | 6.5 | IC50 | ChEMBL |
| P0A7L3 | rplT | Escherichia coli (strain K12) | Pathogen | PF00453 | 6.5 | IC50 | ChEMBL |
| P0A7L8 | rpmA | Escherichia coli (strain K12) | Pathogen | PF01016 | 6.5 | IC50 | ChEMBL |
| P0A7M2 | rpmB | Escherichia coli (strain K12) | Pathogen | PF00830 | 6.5 | IC50 | ChEMBL |
| P0A7M6 | rpmC | Escherichia coli (strain K12) | Pathogen | PF00831 | 6.5 | IC50 | ChEMBL |
| P0A7M9 | rpmE | Escherichia coli (strain K12) | Pathogen | PF01197 | 6.5 | IC50 | ChEMBL |
| P0A7N1 | ykgM | Escherichia coli (strain K12) | Pathogen | PF01197 | 6.5 | IC50 | ChEMBL |
| P0A7N4 | rpmF | Escherichia coli (strain K12) | Pathogen | PF01783 | 6.5 | IC50 | ChEMBL |
| P0A7N9 | rpmG | Escherichia coli (strain K12) | Pathogen | PF00471 | 6.5 | IC50 | ChEMBL |
| P0A7P5 | rpmH | Escherichia coli (strain K12) | Pathogen | PF00468 | 6.5 | IC50 | ChEMBL |
| P0A7Q1 | rpmI | Escherichia coli (strain K12) | Pathogen | PF01632 | 6.5 | IC50 | ChEMBL |
| P0A7Q6 | rpmJ | Escherichia coli (strain K12) | Pathogen | PF00444 | 6.5 | IC50 | ChEMBL |
| P0A7R5 | rpsJ | Escherichia coli (strain K12) | Pathogen | PF00338 | 6.5 | IC50 | ChEMBL |
| P0A7R9 | rpsK | Escherichia coli (strain K12) | Pathogen | PF00411 | 6.5 | IC50 | ChEMBL |
| P0A7S3 | rpsL | Escherichia coli (strain K12) | Pathogen | PF00164 | 6.5 | IC50 | ChEMBL |
| P0A7S9 | rpsM | Escherichia coli (strain K12) | Pathogen | PF00416 | 6.5 | IC50 | ChEMBL |
| P0A7T3 | rpsP | Escherichia coli (strain K12) | Pathogen | PF00886 | 6.5 | IC50 | ChEMBL |
| P0A7T7 | rpsR | Escherichia coli (strain K12) | Pathogen | PF01084 | 6.5 | IC50 | ChEMBL |
| P0A7U3 | rpsS | Escherichia coli (strain K12) | Pathogen | PF00203 | 6.5 | IC50 | ChEMBL |
| P0A7U7 | rpsT | Escherichia coli (strain K12) | Pathogen | PF01649 | 6.5 | IC50 | ChEMBL |
| P0A7V0 | rpsB | Escherichia coli (strain K12) | Pathogen | PF00318 | 6.5 | IC50 | ChEMBL |
| P0A7V3 | rpsC | Escherichia coli (strain K12) | Pathogen | PF07650 PF00189 | 6.5 | IC50 | ChEMBL |
| P0A7V8 | rpsD | Escherichia coli (strain K12) | Pathogen | PF00163 PF01479 | 6.5 | IC50 | ChEMBL |
| P0A7W1 | rpsE | Escherichia coli (strain K12) | Pathogen | PF00333 PF03719 | 6.5 | IC50 | ChEMBL |
| P0A7W7 | rpsH | Escherichia coli (strain K12) | Pathogen | PF00410 | 6.5 | IC50 | ChEMBL |
| P0A7X3 | rpsI | Escherichia coli (strain K12) | Pathogen | PF00380 | 6.5 | IC50 | ChEMBL |
| P0AA10 | rplM | Escherichia coli (strain K12) | Pathogen | PF00572 | 6.5 | IC50 | ChEMBL |
| P0ADY3 | rplN | Escherichia coli (strain K12) | Pathogen | PF00238 | 6.5 | IC50 | ChEMBL |
| P0ADY7 | rplP | Escherichia coli (strain K12) | Pathogen | PF00252 | 6.5 | IC50 | ChEMBL |
| P0ADZ0 | rplW | Escherichia coli (strain K12) | Pathogen | PF00276 | 6.5 | IC50 | ChEMBL |
| P0ADZ4 | rpsO | Escherichia coli (strain K12) | Pathogen | PF00312 | 6.5 | IC50 | ChEMBL |
| P0AG44 | rplQ | Escherichia coli (strain K12) | Pathogen | PF01196 | 6.5 | IC50 | ChEMBL |
| P0AG48 | rplU | Escherichia coli (strain K12) | Pathogen | PF00829 | 6.5 | IC50 | ChEMBL |
| P0AG51 | rpmD | Escherichia coli (strain K12) | Pathogen | PF00327 | 6.5 | IC50 | ChEMBL |
| P0AG55 | rplF | Escherichia coli (strain K12) | Pathogen | PF00347 | 6.5 | IC50 | ChEMBL |
| P0AG59 | rpsN | Escherichia coli (strain K12) | Pathogen | PF00253 | 6.5 | IC50 | ChEMBL |
| P0AG63 | rpsQ | Escherichia coli (strain K12) | Pathogen | PF00366 | 6.5 | IC50 | ChEMBL |
| P0AG67 | rpsA | Escherichia coli (strain K12) | Pathogen | PF00575 | 6.5 | IC50 | ChEMBL |
| P0C018 | rplR | Escherichia coli (strain K12) | Pathogen | PF00861 | 6.5 | IC50 | ChEMBL |
| P60422 | rplB | Escherichia coli (strain K12) | Pathogen | PF03947 PF00181 | 6.5 | IC50 | ChEMBL |
| P60438 | rplC | Escherichia coli (strain K12) | Pathogen | PF00297 | 6.5 | IC50 | ChEMBL |
| P60624 | rplX | Escherichia coli (strain K12) | Pathogen | PF00467 PF17136 | 6.5 | IC50 | ChEMBL |
| P60723 | rplD | Escherichia coli (strain K12) | Pathogen | PF00573 | 6.5 | IC50 | ChEMBL |
| P61175 | rplV | Escherichia coli (strain K12) | Pathogen | PF00237 | 6.5 | IC50 | ChEMBL |
| P62399 | rplE | Escherichia coli (strain K12) | Pathogen | PF00281 PF00673 | 6.5 | IC50 | ChEMBL |
| P68679 | rpsU | Escherichia coli (strain K12) | Pathogen | PF01165 | 6.5 | IC50 | ChEMBL |
| P68919 | rplY | Escherichia coli (strain K12) | Pathogen | PF01386 | 6.5 | IC50 | ChEMBL |
| Q2EEQ2 | ykgO | Escherichia coli (strain K12) | Pathogen | PF00444 | 6.5 | IC50 | ChEMBL |
DrugBank Target Actions (7)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| Q9UM07 | PADI4 | Protein-arginine deiminase type-4 | inhibitor | targets |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | transporters |
| Q92887 | ABCC2 | ATP-binding cassette sub-family C member 2 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |
| Q92887 | ABCC2 | ATP-binding cassette sub-family C member 2 | substrate | transporters |