Compound Detail
CHEMBL529
AZITHROMYCIN 💊 Approved Drug
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💊 Approved Drug
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
Basic Information
| ChEMBL ID | CHEMBL529 |
| Name | AZITHROMYCIN |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | MQTOSJVFKKJCRP-BICOPXKESA-N |
| Therapeutic | ✓ Yes |
15
Targets
82
Activities
3
Assay Types
30
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms
Molecular Properties
749.0
MW (Da)
1.90
ALogP
14
HBA
5
HBD
180.1
PSA (Ų)
0.24
QED
2
Ro5 Violations
7
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1991 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Bacterial 70S ribosome inhibitor | INHIBITOR | Bacterial 70S ribosome | ✓ | ✓ |
Indications
Bacterial Infections Bronchitis, Chronic Conjunctivitis, Bacterial Cystic Fibrosis Eye Infections HIV Infections Infections Otitis Media Otitis Media Pelvic Inflammatory Disease Pharyngitis Pneumonia Pulmonary Disease, Chronic Obstructive Sinusitis Tonsillitis Tonsillitis Urethritis Uterine Cervicitis Abdominal Pain Acne Vulgaris
ATC Classification
J01FA10
azithromycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA26
azithromycin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
Activity Summary
IC50 69 meas. best 8.59
EC50 8 meas. best 9.3
Kd 5 meas. best 5.85
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Mycoplasma genitalium CHEMBL5465483 | EC50 | 9.3 | 9.3 | 0.5 | 1 |
| Naegleria fowleri CHEMBL3301413 | IC50 | 8.59 | 8.55 | 2.6 | 2 |
| Plasmodium falciparum CHEMBL364 | IC50 | 7.51 | 6.1578 | 31.0 | 46 |
| Streptococcus CHEMBL612313 | EC50 | 7.18 | 7.18 | 66.0 | 1 |
| Streptococcus pneumoniae CHEMBL347 | IC50 | 6.77 | 6.77 | 170.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 6.54 | 5.81 | 292.0 | 7 |
| Bacterial 70S ribosome CHEMBL2363135 | IC50 | 6.52 | 6.52 | 300.0 | 1 |
| Toxoplasma gondii CHEMBL612888 | IC50 | 6.22 | 5.208 | 600.0 | 5 |
| Chlamydia trachomatis CHEMBL614606 | IC50 | 6.14 | 6.14 | 727.0 | 1 |
| Unchecked CHEMBL612545 | Kd | 5.85 | 5.656 | 1410.0 | 5 |
| SARS-CoV-2 CHEMBL4303835 | EC50 | 5.67 | 5.67 | 2120.0 | 2 |
| dengue virus type 2 CHEMBL613966 | EC50 | 5.43 | 5.43 | 3710.0 | 1 |
| Zaire ebolavirus CHEMBL4513181 | EC50 | 5.29 | 5.29 | 5100.0 | 1 |
| Pseudomonas aeruginosa CHEMBL348 | IC50 | 5.18 | 5.03 | 6600.0 | 3 |
| Zika virus CHEMBL4296612 | EC50 | 5.18 | 5.18 | 6590.0 | 1 |
| Influenza A virus CHEMBL613740 | EC50 | 4.17 | 4.17 | 68000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 3390.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 249.1 | - | Chlorocebus sabaeus |
| CL | 10.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 9.6 | mL.min-1.kg-1 | Homo sapiens |
| CL | 10.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 10.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 11.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 16.0 | mL.min-1.kg-1 | Mus musculus |
| CL | 23.2 | mL.min-1.kg-1 | Mus musculus |
| Cmax | 1100.0 | nM | Homo sapiens |
| Cmax | 534.05 | nM | Homo sapiens |
| Cmax | 1335.11 | nM | Homo sapiens |
| Cmax | 534.05 | nM | Homo sapiens |
| Cmax | 4272.36 | nM | Homo sapiens |
| Cmax | 1255.01 | nM | Homo sapiens |
| Cmax | 2683.58 | nM | Homo sapiens |
| Cmax | 894.53 | nM | Homo sapiens |
| Cmax | 467289.72 | nM | Homo sapiens |
| F | 33.0 | % | Rattus norvegicus |
| F | 72.0 | % | Mus musculus |
| Fu | 0.88 | - | Homo sapiens |
| Fu | 0.88 | - | Homo sapiens |
| Fu | 0.88 | - | Homo sapiens |
| Fu | 0.0069 | - | Mus musculus |
| MRT | 57.0 | hr | Homo sapiens |
| T1/2 | 0.7333 | hr | Mus musculus |
| T1/2 | 2.3 | hr | Mus musculus |
| T1/2 | 68.0 | hr | Homo sapiens |
| T1/2 | 74.0 | hr | Homo sapiens |
| T1/2 | 69.0 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL3885881 | Rattus norvegicus | 432 |
| 19884376 | 10.1128/aac.01123-09 | Streptococcus pneumoniae | 87 |
| 19307366 | 10.1128/aac.01531-08 | Streptococcus pneumoniae | 55 |
| 17938189 | 10.1128/aac.01229-07 | Streptococcus pneumoniae | 49 |
| 17876003 | 10.1128/aac.00827-07 | Streptococcus pneumoniae | 48 |
| 19188376 | 10.1128/aac.01264-08 | Pseudomonas aeruginosa | 44 |
| 20231397 | 10.1128/aac.01424-09 | Mus musculus | 44 |
| 17620382 | 10.1128/aac.01011-06 | Pseudomonas aeruginosa | 43 |
| 17145801 | 10.1128/aac.01033-06 | Burkholderia pseudomallei | 37 |
| 17908940 | 10.1128/aac.00971-07 | Streptococcus pneumoniae | 34 |
| 20145081 | 10.1128/aac.00737-08 | Bacillus anthracis | 29 |
| 19738019 | 10.1128/aac.00724-09 | NON-PROTEIN TARGET | 28 |
| 18443117 | 10.1128/aac.00310-08 | Streptococcus pneumoniae | 27 |
| 18362189 | 10.1128/aac.01620-07 | Streptococcus pneumoniae | 27 |
| 17116666 | 10.1128/aac.01150-06 | Streptococcus pneumoniae | 26 |
| 21428405 | 10.1021/jm101593u | Toxoplasma gondii | 25 |
| 20231401 | 10.1128/aac.01565-09 | Staphylococcus epidermidis | 24 |
| 17954687 | 10.1128/aac.00607-07 | Haemophilus influenzae | 22 |
| 17110371 | 10.1074/jbc.m608615200 | Plasmodium falciparum | 22 |
| 20498312 | 10.1128/aac.01678-09 | NON-PROTEIN TARGET | 22 |
Data from ChEMBL 36 via Core Engine