Troleandomycin
drugOn this page
Also known as AcetyloleandomycinNSC-108166Oleandomycin (as troleandomycin)Oleandomycin triacetate esterTriacetyloleandomycinTroleandomicinaTroleandomycineTriactyloleandomycin
Summary
Troleandomycin (CHEMBL564085) is an approved small-molecule EC 1.14.13.97 (taurochenodeoxycholate 6α-hydroxylase) inhibitor (ATC J01FA08) targeting CYP3A4; indicated across 2 conditions including bacterial infectious disease and osteomyelitis.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01FA08
- Targets: 1 (CYP3A4)
- Indications: 2 conditions
- Chemistry: 814 Da · C41H67NO15
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL564085 |
| Name | Troleandomycin |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 202225 |
| ChEBI | CHEBI:45735 |
| ATC | J01FA08 |
| Molecular formula | C41H67NO15 |
| Molecular weight | 814 |
| InChIKey | LQCLVBQBTUVCEQ-QTFUVMRISA-N |
SMILES: C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C
IUPAC name: [(3R,5S,6S,7R,8S,9R,12R,13S,14S,15R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
ChEBI definition: A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.
Pharmacological roles (ChEBI): EC 1.14.13.97 (taurochenodeoxycholate 6α-hydroxylase) inhibitor.
Other ChEBI roles (chemical / environmental): xenobiotic.
Also known as: Acetyloleandomycin, NSC-108166, Oleandomycin (as troleandomycin), Oleandomycin triacetate ester, Triacetyloleandomycin, Troleandomicina, Troleandomycin, Troleandomycine, troleandomycin, TROLEANDOMYCIN, Triactyloleandomycin, TROLEANDOMYCINE
Patent coverage: 3,676 distinct patent families (14,175 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| CYP3A4 | CYP3A4 | Inhibition | 7.8 | 0% | P08684 |
Broader ChEMBL bioactivity targets: 2 (assay-derived). Sample: Cytochrome P450 3A4, ATP-dependent translocase ABCB1.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 9 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| CYP3A4 | 5.1 | IC50 | 7998 | nM | CHEMBL_ACT_2686207 |
Target pathways
Aggregated over 1 target gene(s): CYP3A4.
Top Reactome pathways
7 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Phase I - Functionalization of compounds | 1 | CYP3A4 |
| Xenobiotics | 1 | CYP3A4 |
| Aflatoxin activation and detoxification | 1 | CYP3A4 |
| Biosynthesis of maresin-like SPMs | 1 | CYP3A4 |
| Aspirin ADME | 1 | CYP3A4 |
| Atorvastatin ADME | 1 | CYP3A4 |
| Prednisone ADME | 1 | CYP3A4 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| lipid hydroxylation | 1 |
| lipid metabolic process | 1 |
| steroid catabolic process | 1 |
| xenobiotic metabolic process | 1 |
| steroid metabolic process | 1 |
| cholesterol metabolic process | 1 |
| androgen metabolic process | 1 |
| estrogen metabolic process | 1 |
| alkaloid catabolic process | 1 |
| monoterpenoid metabolic process | 1 |
| xenobiotic catabolic process | 1 |
| vitamin D metabolic process | 1 |
| vitamin D catabolic process | 1 |
| retinol metabolic process | 1 |
| retinoic acid metabolic process | 1 |
Indications & clinical
Indications
2 indications (1 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 |
|---|---|---|---|
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| osteomyelitis | 0 | MONDO:0005246 | EFO:0003102 |
Clinical trials
Total trials: 0.
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
583 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | CYP3A4 |
| Elagolix | ChEMBL + PubChem | Phase 4 (approved) | CYP3A4 |
| SAXAGLIPTIN | ChEMBL + PubChem | Phase 4 (approved) | CYP3A4 |
| ABIRATERONE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| ACETAMINOPHEN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| ACRISORCIN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| ALOSETRON | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMINOGLUTETHIMIDE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMPICILLIN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMPRENAVIR | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AMSACRINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| APREPITANT | ChEMBL | Phase 4 (approved) | CYP3A4 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| ATOMOXETINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| ATORVASTATIN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AZATHIOPRINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| AZITHROMYCIN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BACLOFEN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BENDROFLUMETHIAZIDE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BENZNIDAZOLE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BENZONATATE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BENZTHIAZIDE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BERBERINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BIFONAZOLE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BITHIONOL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BITHIONOLATE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BRETYLIUM TOSYLATE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BROMHEXINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BUDESONIDE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BUPIVACAINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BUSPIRONE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| BUTAMBEN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CAPSAICIN | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CARBETAPENTANE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CARBIDOPA | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CARFILZOMIB | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CARISOPRODOL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CEFDITOREN PIVOXIL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CHLORAMPHENICOL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CHLOROXINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CHLORPROPAMIDE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CHOLECALCIFEROL | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CHOLIC ACID | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CIMETIDINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | CYP3A4 |
| CISAPRIDE | ChEMBL | Phase 4 (approved) | CYP3A4 |
Related Atlas pages
- Genes: CYP3A4
- Diseases: bacterial infectious disease
- Drugs: Dihydroergotamine, Elagolix, Saxagliptin, Abiraterone, Acetaminophen, Acrisorcin, Alosetron, Aminoglutethimide, Amiodarone, Amitriptyline, Amlodipine, Amoxapine, Ampicillin, Amprenavir, Amsacrine, Apomorphine, Aprepitant, Astemizole, Atomoxetine, Atorvastatin, Azathioprine, Azelastine, Azithromycin, Baclofen, Bendroflumethiazide, Benzbromarone, Benznidazole, Benzonatate, Benzthiazide, Bepridil, Berberine, Bifonazole, Bithionol, Bromhexine, Bromocriptine, Bromperidol, Budesonide, Bupivacaine, Buspirone, Butamben, Candesartan Cilexetil, Cannabidiol, Capsaicin, Carbetapentane, Carbidopa, Carfilzomib, Carisoprodol, Cefditoren Pivoxil, Celecoxib, Chloramphenicol, Chloroxine, Chlorpromazine, Chlorpropamide, Cholecalciferol, Cholic Acid, Cimetidine, Cinnarizine, Cisapride