Vinflunine

Summary

Vinflunine (CHEMBL2110725) is an approved small-molecule antineoplastic agent (ATC L01CA05); indicated across 17 conditions including neoplasm and urothelial carcinoma.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L01CA05
• Indications: 17 conditions
• Clinical trials: 31
• Chemistry: 816.9 Da · C45H54F2N4O8

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL2110725
Name	Vinflunine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	10629256
ChEBI	CHEBI:90241
ATC	L01CA05
Molecular formula	C45H54F2N4O8
Molecular weight	816.9
InChIKey	NMDYYWFGPIMTKO-KLCPSUAYSA-N

SMILES: CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)[C@]6(C[C@@H]7C[C@H](CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C

IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(12S,14S,16R)-16-(1,1-difluoroethyl)-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

ChEBI definition: An organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethyl group attached to this ring has been replaced by a 1,1-difluoroethyl group.

Pharmacological roles (ChEBI): antineoplastic agent.

Also known as: Vinflunina, Vinflunine, vinflunine, VINFLUNINE

Parent form; salt/anhydrous children: CHEMBL2105629

Patent coverage: 66 distinct patent families (117 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

No target linkage available.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

4 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
neoplasm	3	MONDO:0005070	EFO:0000616
urothelial carcinoma	3	MONDO:0040679	EFO:0008528
breast neoplasm	3	MONDO:0021100	MONDO:0007254
urinary bladder neoplasm	3	MONDO:0004987	EFO:0000294

6 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
small cell lung carcinoma	2	MONDO:0008433	EFO:0000702
non-small cell lung carcinoma	2	MONDO:0005233	EFO:0003060
transitional cell carcinoma	2	MONDO:0006474	EFO:1000601
penile neoplasm	2	MONDO:0006895	EFO:1001094
gastric neoplasm	2	MONDO:0021085	MONDO:0001056
lung neoplasm	2	MONDO:0021117	MONDO:0008903

7 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 31.

Phase distribution

Phase	Trials
PHASE3	11
PHASE2	11
PHASE1	5
PHASE2/PHASE3	3
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03390504	PHASE3	ACTIVE_NOT_RECRUITING	A Study of Erdafitinib Compared With Vinflunine or Docetaxel or Pembrolizumab in Participants With Advanced Urothelial Cancer and Selected Fibroblast Growth Factor Receptor (FGFR) Gene Aberrations
NCT07419295	PHASE3	RECRUITING	A Clinical Trial of Sacituzumab Tirumotecan (Sac-TMT, MK-2870) to Treat Urothelial Cancer (MK-2870-031)
NCT00315237	PHASE3	COMPLETED	Phase III Trial of Vinflunine Plus Best Supportive Care vs. Best Supportive Care in Patients With Transitional Cell Carcinoma (TCC) of the Urothelial Tract
NCT00359476	PHASE2/PHASE3	TERMINATED	A Study of Vinflunine in Patients With Gastric Cancer
NCT00389155	PHASE2/PHASE3	COMPLETED	First-Line Treatment of Advanced Bladder Cancer Randomized vs. Gemcitabine ± Vinflunine in Patients Ineligible to Receive Cisplatin-Based Therapy
NCT01091168	PHASE3	COMPLETED	Trial of Vinflunine Versus Alkylating Agent in Metastatic Breast Cancer
NCT01830231	PHASE2/PHASE3	UNKNOWN	Cabazitaxel vs. Vinflunine in Metastatic or Locally Advanced Transitional Cell Carcinoma of the Urothelium (TCCU)
NCT01953003	PHASE3	COMPLETED	Phase III Study of Vinflunine Plus Capecitabine Versus Capecitabine Alone in Patients With Advanced Breast Cancer
NCT02054338	PHASE3	TERMINATED	A Study of Vinflunine Plus Gemcitabine Versus Paclitaxel Plus Gemcitabine in Patients With Advanced Breast Cancer
NCT02256436	PHASE3	COMPLETED	A Study of Pembrolizumab (MK-3475) Versus Paclitaxel, Docetaxel, or Vinflunine for Participants With Advanced Urothelial Cancer (MK-3475-045/KEYNOTE-045)
NCT02302807	PHASE3	COMPLETED	A Study of Atezolizumab Compared With Chemotherapy in Participants With Locally Advanced or Metastatic Urothelial Bladder Cancer [IMvigor211]
NCT02347332	PHASE3	COMPLETED	Phase III Study of Vinflunine Plus Methotrexate Versus Methotrexate Alone in Patients With Head and Neck Cancer
NCT03474107	PHASE3	COMPLETED	A Study to Evaluate Enfortumab Vedotin Versus (vs) Chemotherapy in Subjects With Previously Treated Locally Advanced or Metastatic Urothelial Cancer (EV-301)
NCT04527991	PHASE3	COMPLETED	Study of Sacituzumab Govitecan Versus Physician’s Choice of Treatment in Participants With Urothelial Cancer That Cannot Be Removed or Has Spread
NCT00101608	PHASE2	COMPLETED	Vinflunine in Patients With Locally Advanced or Metastatic Transitional Cell Carcinoma of the Urothelium
NCT00251446	PHASE2	COMPLETED	A Phase II Single Arm Trial of Single-agent Vinflunine as Second-line Treatment of Advanced Non-Small Cell Lung Cancer
NCT00284154	PHASE2	COMPLETED	Vinflunine in the Treatment of Patients With Relapsed Extensive Small Cell Lung Cancer
NCT00284180	PHASE2	COMPLETED	Vinflunine Plus Trastuzumab in Human Epidermal Growth Factor Receptor 2 (HER2neu) Over-Expressing Metastatic Breast Cancer
NCT00450515	PHASE2	WITHDRAWN	Vinflunine and Capecitabine in Treating Patients With Previously Treated Metastatic Breast Cancer
NCT00519831	PHASE2	TERMINATED	Ph II of Vinflunine and Cetuximab in Second Line Treatment of NSCLC
NCT00545766	PHASE2	COMPLETED	Vinflunine in Hormone Refractory Prostate Cancer (HRPC)
NCT01529411	PHASE2	COMPLETED	Clinical Trial With Vinflunine as Maintenance Therapy in Metastatic Urothelial Cancer
NCT01599013	PHASE2	COMPLETED	JAVLOR Association Study in CDDP-unfit Patients With Advanced Transitional Cell Carcinoma: Gemcitabine Versus Carboplatin
NCT02057913	PHASE2	COMPLETED	A Phase II Trial of Vinflunine Chemotherapy in Locally-advanced and Metastatic Carcinoma of the Penis (VinCaP)
NCT02665039	PHASE2	COMPLETED	A Trial With Vinflunine in Patients With Metastatic Bladder Cancer and Impaired Renal Function
NCT02845050	PHASE1/PHASE2	WITHDRAWN	Phase Ib/II Study Assessing the Neo-adjuvant Combination Therapy of Vinflunine With Cisplatin Followed by Radical Cystectomy in Patients With Muscle-invasive Bladder Cancer (JaNEO)
NCT00320073	PHASE1	COMPLETED	Vinflunine and Erlotinib or Pemetrexed in Treating Patients With Unresectable or Metastatic Solid Tumors
NCT00362830	PHASE1	COMPLETED	A Study of the Alternative Administration of Ixabepilone and Vinflunine
NCT00388557	PHASE1	COMPLETED	Effect of Ketoconazole on the Pharmacokinetics of Vinflunine
NCT00534807	PHASE1	WITHDRAWN	A Study of the Interaction of Rifampin and Vinflunine in Subjects With Advanced Cancer
NCT01844947	PHASE1	COMPLETED	Phase I Study With Sorafenib in Addition to Vinflunine in Metastatic Transitional Cell Carcinoma of the Urothelial Tract

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).