Patupilone
drug drugOn this page
Also known as (-)-epothilone bEpithilone bEPO 906EPO 906AEpo bEPO-906EPO-906AEPO906EPO906AEpothilone bGNF-PF-193PatupilonaSID50125842SID520207Epothilon BPatupilone (EPO906Epothilone B)
Summary
Patupilone (CHEMBL94657) is a phase-3 clinical-stage small-molecule antineoplastic agent; indicated across 18 conditions including peritoneal neoplasm and fallopian tube neoplasm.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- Indications: 18 conditions
- Clinical trials: 26
- Chemistry: 507.7 Da · C27H41NO6S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL94657 |
| Name | Patupilone |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 448013 |
| ChEBI | CHEBI:31550 |
| Molecular formula | C27H41NO6S |
| Molecular weight | 507.7 |
| InChIKey | QXRSDHAAWVKZLJ-PVYNADRNSA-N |
SMILES: C[C@H]1CCC[C@@]2([C@@H](O2)C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C)C
IUPAC name: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
ChEBI definition: An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer).
Pharmacological roles (ChEBI): apoptosis inducer, antineoplastic agent, microtubule-stabilising agent.
Also known as: (-)-epothilone b, Epithilone b, EPO 906, EPO 906A, Epo b, EPO-906, EPO-906A, EPO906, EPO906A, Epothilone b, GNF-PF-193, Patupilona
Patent coverage: 3,660 distinct patent families (14,934 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
Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Nuclear receptor ROR-gamma, Tubulin, Nuclear receptor subfamily 1 group I member 2, Nuclear receptor subfamily 1 group I member 2.
Bioactivity
ChEMBL activities: 3 potent at pChembl ≥ 5 of 6 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| TUBB4A | 8.74 | IC50 | 1.8 | nM | CHEMBL_ACT_29153392 |
| TUBB4A | 8.46 | IC50 | 3.5 | nM | CHEMBL_ACT_18807128 |
| Q9R1A7 | 8 | EC50 | 10 | nM | CHEMBL_ACT_15463827 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
14 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.
| Disease (in trials) | Phase | MONDO | EFO |
|---|---|---|---|
| peritoneal neoplasm | 3 | MONDO:0006901 | EFO:1001100 |
| fallopian tube neoplasm | 3 | MONDO:0021092 | MONDO:0002158 |
| ovarian cancer | 3 | MONDO:0008170 | MONDO:0008170 |
| hepatocellular carcinoma | 2 | MONDO:0007256 | EFO:0000182 |
| prostate adenocarcinoma | 2 | MONDO:0005082 | EFO:0000673 |
| melanoma | 2 | MONDO:0005105 | EFO:0000756 |
| kidney neoplasm | 2 | MONDO:0021163 | EFO:0003865 |
| breast neoplasm | 2 | MONDO:0021100 | EFO:0003869 |
| carcinoid tumor | 2 | MONDO:0005369 | EFO:0004243 |
| colonic neoplasm | 2 | MONDO:0005401 | EFO:0004288 |
| neuroendocrine neoplasm | 2 | MONDO:0019496 | EFO:1001901 |
| neoplasm | 1 | MONDO:0005070 | EFO:0000616 |
| glioblastoma | 1 | MONDO:0018177 | EFO:0000519 |
| non-small cell lung carcinoma | 1 | MONDO:0005233 | EFO:0003060 |
4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 26.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 11 |
| PHASE1 | 11 |
| PHASE1/PHASE2 | 3 |
| PHASE3 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00262990 | PHASE3 | COMPLETED | Patupilone Versus Doxorubicin in Patients With Ovarian, Primary Fallopian, or Peritoneal Cancer |
| NCT00035087 | PHASE2 | COMPLETED | EPO906 Therapy in Patients With Advanced Colorectal Cancer |
| NCT00035100 | PHASE2 | COMPLETED | EPO906 Therapy in Patients With Advanced Ovarian, Primary Fallopian, or Primary Peritoneal Cancer |
| NCT00035113 | PHASE2 | COMPLETED | EPO906 Therapy in Patients With Prostate Cancer |
| NCT00035126 | PHASE2 | COMPLETED | EPO906 Therapy in Patients With Advanced Breast Cancer |
| NCT00035165 | PHASE2 | COMPLETED | EPO906 Therapy in Patients With Advanced Melanoma |
| NCT00035243 | PHASE2 | COMPLETED | EPO906 Therapy in Patients With Advanced Kidney Cancer |
| NCT00159484 | PHASE1/PHASE2 | COMPLETED | Phase I/II Study of Celebrex and EPO906 in Patients With Metastatic Colorectal Cancer |
| NCT00171834 | PHASE1/PHASE2 | COMPLETED | Dose Escalating Study of the Safety and Efficacy of Patupilone, q3w, in Patients With Non-small Cell Lung Cancer |
| NCT00219297 | PHASE2 | COMPLETED | Study of Patupilone in Patients With Brain Metastasis From Non-small Cell Lung Cancer |
| NCT00273312 | PHASE2 | COMPLETED | Patupilone Activity in Advanced/Metastatic Hepatocellular Carcinoma |
| NCT00407251 | PHASE2 | COMPLETED | Study of Patupilone in Prostate Cancer Patients Who Progress After Hormone Therapy and Docetaxel Chemotherapy |
| NCT00411528 | PHASE2 | COMPLETED | Efficacy and Safety of Patupilone in Men (≥18 Years) With Metastatic Hormone Refractory Prostate Cancer |
| NCT00450866 | PHASE2 | COMPLETED | Epothilone B in Treating Patients With CNS Metastases From Breast Cancer |
| NCT00715013 | PHASE1/PHASE2 | COMPLETED | Patupilone (EPO 906) in Patients With Recurrent or Progressive Glioblastoma |
| NCT00412789 | PHASE1 | COMPLETED | Efficacy and Safety of Patupilone in Patients With Advanced Solid Tumors in Japan |
| NCT00420524 | PHASE1 | COMPLETED | A Study of Patupilone in Patients With Advanced Solid Tumors and Varying Degrees of Hepatic Function |
| NCT00420615 | PHASE1 | COMPLETED | Evaluate the Effects of Patupilone on the Pharmacokinetics of Midazolam and Omeprazole in Patients With Advanced Malignancies |
| NCT00421044 | PHASE1 | COMPLETED | A Study of Patupilone in Patients With Advanced Solid Tumors and Varying Degrees of Hepatic Function |
| NCT00426140 | PHASE1 | COMPLETED | Pharmacokinetics of Patupilone After a Single Intravenous Administration in Patients With Advance Solid Tumor Malignancies. |
| NCT00426582 | PHASE1 | COMPLETED | Combination Trial of Patupilone and Carboplatin in Adult Patients With Advanced Solid Tumors |
| NCT00442741 | PHASE1 | WITHDRAWN | Evaluate the Effects of Patupilone on the Pharmacokinetics of Midazolam and Omeprazole in Patients With Advanced Malignancies (Extension) |
| NCT00448396 | PHASE1 | COMPLETED | Evaluate the Effects of Patupilone on the Pharmacokinetics and Pharmacodynamics of Warfarin in Patients With Advanced Malignancies |
| NCT00468260 | PHASE1 | TERMINATED | The Effects of Patupilone on the Pharmacokinetics and Pharmacodynamics of Warfarin in Patients With Advanced Malignancies |
| NCT00496600 | PHASE1 | COMPLETED | Phase I Study of Patupilone and RAD001 |
| NCT00969046 | PHASE1 | COMPLETED | Dose-Escalation Study in Advanced Colon Cancer Patients |
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).