Telithromycin
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Also known as HMR 3647HMR-3647HMR3647KetekLevviaxNSC-758940TelithromycineTelitromicinaTelithromycin 1SID144205007SID144205756
Summary
Telithromycin (CHEMBL1136) is an approved small molecule (ATC J01FA15); indicated across 15 conditions including pneumonia and bacterial infectious disease.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01FA15
- Indications: 15 conditions
- Clinical trials: 24
- Chemistry: 812 Da · C43H65N5O10
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1136 |
| Name | Telithromycin |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 3002190 |
| ATC | J01FA15 |
| Molecular formula | C43H65N5O10 |
| Molecular weight | 812 |
| InChIKey | LJVAJPDWBABPEJ-PNUFFHFMSA-N |
SMILES: CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=C4)C5=CN=CC=C5)C
IUPAC name: (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
Also known as: HMR 3647, HMR-3647, HMR3647, Ketek, Levviax, NSC-758940, Telithromycin, Telithromycine, Telitromicina, telithromycin, Telithromycin 1, TELITHROMYCIN
Patent coverage: 4,240 distinct patent families (15,927 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 15,882 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 9 (assay-derived). Sample: Solute carrier organic anion transporter family member 1B1, Solute carrier organic anion transporter family member 1B3, ATP-binding cassette sub-family C member 4, Prostaglandin G/H synthase 1, Bacterial 70S ribosome, Cytochrome P450 3A, Voltage-gated inwardly rectifying potassium channel KCNH2, Cytochrome P450 3A4, Bile salt export pump.
Bioactivity
ChEMBL activities: 7 potent at pChembl ≥ 5 of 12 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| CYP3A4 | 8.62 | Ki | 2.4 | nM | CHEMBL_ACT_2924244 |
| P02358 | 8.19 | Kd | 6.4 | nM | CHEMBL_ACT_15105520 |
| SLCO1B1 | 5.46 | IC50 | 3467 | nM | CHEMBL_ACT_13800624 |
| ABCB11 | 5.4 | IC50 | 4000 | nM | CHEMBL_ACT_18051772 |
| ABCB11 | 5.3 | IC50 | 5000 | nM | CHEMBL_ACT_18129057 |
| SLCO1B3 | 5.23 | IC50 | 5888 | nM | CHEMBL_ACT_13798625 |
| ABCC4 | 5.15 | IC50 | 7100 | nM | CHEMBL_ACT_18130827 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
15 indications (10 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| pneumonia | 4 | MONDO:0005249 | EFO:0003106 |
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| tonsillitis | 4 | MONDO:0001039 | HP:0011110 |
| pharyngitis | 4 | MONDO:0002258 | MONDO:0002258 |
| chronic bronchitis | 4 | MONDO:0005607 | EFO:0006505 |
| sinusitis | 4 | MONDO:0005961 | EFO:0007486 |
| bacterial pneumonia | 4 | MONDO:0004652 | EFO:1001272 |
| otitis media | 3 | MONDO:0005441 | EFO:0004992 |
| maxillary sinusitis | 3 | MONDO:0005842 | EFO:0007361 |
| suppurative otitis media | 3 | MONDO:0005975 | EFO:0007503 |
| scrub typhus | 3 | MONDO:0019365 | EFO:0007480 |
| asthma | 3 | MONDO:0004979 | MONDO:0004979 |
3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 24.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 12 |
| PHASE3 | 10 |
| PHASE2 | 1 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00132938 | PHASE4 | COMPLETED | PERSPECTIVE: Telithromycin - Acute Exacerbation of Chronic Bronchitis |
| NCT00132951 | PHASE4 | TERMINATED | KEYS: Study Comparing Clinical Health Outcomes of Telithromycin Versus Azithromycin in Outpatients With Community-acquired Lower Respiratory Tract Infections |
| NCT00174694 | PHASE4 | COMPLETED | CHOOSE : Telithromycin, Acute Bacterial Sinusitis |
| NCT00237445 | PHASE4 | TERMINATED | Study Comparing the Clinical Efficacy and Health Outcomes of Outpatients With Mild to Moderate Community-Acquired Pneumonia (CAP) Treated With Either Telithromycin Once Daily for 7 Days, or Azithromycin Once Daily for 5 Days |
| NCT00245440 | PHASE4 | TERMINATED | Study to Measure the Impact of Antibiotics on Bacterial Flora in Adults With Acute Sinusitis |
| NCT00245453 | PHASE4 | WITHDRAWN | Outpatient Registry Trial of Respiratory Tract Infections in Adults |
| NCT00261105 | PHASE4 | COMPLETED | Telithromycin in Respiratory Tract Infections |
| NCT00288223 | PHASE4 | TERMINATED | Telithromycin in Acute Exacerbation of Chronic Bronchitis |
| NCT00315601 | PHASE4 | TERMINATED | Intrapulmonary Pharmacokinetics of Antibiotics |
| NCT00538018 | PHASE4 | COMPLETED | Telithromycin, Treating Adult Outpatients With Mild to Moderate Community-acquired Pneumonia (CAP) in High Bacterial Resistance Areas |
| NCT00538148 | PHASE4 | COMPLETED | Telithromycin: in the Treatment of Acute Exacerbation of Chronic Bronchitis in Adult Outpatients With COPD |
| NCT00546676 | PHASE4 | COMPLETED | Ketek in CAP / AECB in Ambulatory Adult Patients |
| NCT00174811 | PHASE3 | TERMINATED | Comparative Study to Evaluate the Efficacy and Safety of Telithromycin Given Once Daily Versus Cefuroxime Axetil Given Twice Daily in Children With Middle Ear Infections |
| NCT00273520 | PHASE3 | COMPLETED | TELICAST : Telithromycin in Acute Exacerbations of Asthma |
| NCT00315003 | PHASE3 | TERMINATED | TELI COM - Telithromycin in Children With Otitis Media |
| NCT00315042 | PHASE3 | TERMINATED | TELI TON - Telithromycin in Tonsillitis |
| NCT00315549 | PHASE3 | TERMINATED | TELI TAD - Telithromycin in Tonsillitis in Adolescents and Adults |
| NCT00351182 | PHASE3 | COMPLETED | Controlled Trial: 5-day Course of Telithromycin Versus Doxycycline for the Treatment of Mild to Moderate Scrub Typhus |
| NCT00408135 | PHASE3 | COMPLETED | Japanese Study Evaluating Safety, Efficacy and Acceptability of Telithromycin in Children With Infections |
| NCT00537563 | PHASE3 | COMPLETED | AMS VS MOXI Ketek vs Avelox in AMS |
| NCT00638534 | PHASE3 | COMPLETED | Japanese Study Evaluating the Effects of Telithromycin in Children With Acute Otitis Media |
| NCT00638859 | PHASE3 | COMPLETED | Japanese Study Evaluating the Effects of Telithromycin in Children With Community-Acquired Pneumonia |
| NCT00270517 | PHASE2 | UNKNOWN | Comparative Study of EDP-420 Versus Another Antibiotic in the Treatment of Community Acquired Pneumonia |
| NCT01434173 | Not specified | COMPLETED | Risk of Acute Liver Injury in Users of Antimicrobials |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).