Vinorelbine

Summary

Vinorelbine (CHEMBL553025) is an approved small-molecule antineoplastic agent (ATC L01CA04); indicated across 39 conditions including neoplasm and non-small cell lung carcinoma; with CIViC clinical evidence for 4 variant-indication associations (e.g. RRM1 Underexpression in lung non-small cell carcinoma).

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L01CA04
• Indications: 39 conditions
• Clinical trials: 277
• Precision-oncology evidence (CIViC): 4 variant–indication associations
• Chemistry: 778.9 Da · C45H54N4O8

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL553025
Name	Vinorelbine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5311497
ChEBI	CHEBI:480999
ATC	L01CA04
Molecular formula	C45H54N4O8
Molecular weight	778.9
InChIKey	GBABOYUKABKIAF-IELIFDKJSA-N

SMILES: CCC1=C[C@H]2C[C@@](C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC

IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(12S,14R)-16-ethyl-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-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: A vinca alkaloid with a norvinblastine skeleton.

Pharmacological roles (ChEBI): antineoplastic agent, photosensitizing agent.

Also known as: Navelbin, NSC-760087, Vinorelbina, Vinorelbine, Vinorelbine base, anhydrovinblastine, vinorelbine, AVLB, Anhydrovinblastine, SID29217724, SID124893200, VINORELBINE

Parent form; salt/anhydrous children: CHEMBL538943

Patent coverage: 34,692 distinct patent families (142,159 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 142,126 (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: 8 (assay-derived). Sample: Fructose-bisphosphate aldolase, 4’-phosphopantetheinyl transferase ffp, Menin/Histone-lysine N-methyltransferase MLL, Tubulin, Substance-K receptor, Mu-type opioid receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Cytochrome P450 3A4.

Bioactivity

ChEMBL activities: 9 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
TUBB4A	9.51	IC50	0.31	nM	CHEMBL_ACT_25553928
TACR2	6.27	Ki	535.5	nM	CHEMBL_ACT_7787375
TUBB4A	6.16	IC50	700	nM	CHEMBL_ACT_15185286
MEN1	6	Potency	1000	nM	CHEMBL_ACT_4579786
CYP3A4	6	IC50	1000	nM	CHEMBL_ACT_7785623
TACR2	5.79	IC50	1606	nM	CHEMBL_ACT_7787374
TUBB4A	5.7	IC50	2000	nM	CHEMBL_ACT_15673952
KCNH2	5.26	AC50	5500	nM	CHEMBL_ACT_25117685
OPRM1	5.17	AC50	6755	nM	CHEMBL_ACT_25158210

Target pathways

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

Indications & clinical

Indications

39 indications (2 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
neoplasm	4	MONDO:0005070	EFO:0000616
non-small cell lung carcinoma	3	MONDO:0005233	EFO:0003060
mesothelioma	3	MONDO:0005065	EFO:0000588
breast neoplasm	3	MONDO:0021100	EFO:0003869
Hodgkins lymphoma	3	MONDO:0004952	EFO:0000183
carcinoma	3	MONDO:0004993	EFO:0000313
malignant pleural mesothelioma	3	MONDO:0005112	EFO:0000770
lung carcinoma	3	MONDO:0005138	EFO:0001071
esophageal squamous cell carcinoma	3	MONDO:0005580	EFO:0005922
non-Hodgkin lymphoma	3	MONDO:0018908	EFO:0005952
alveolar rhabdomyosarcoma	3	MONDO:0009994	EFO:0000248
embryonal rhabdomyosarcoma	3	MONDO:0009993	EFO:0000437
triple-negative breast carcinoma	3	MONDO:0005494	EFO:0005537
lung neoplasm	3	MONDO:0021117	MONDO:0008903
HER2 positive breast carcinoma	3	MONDO:0006244	EFO:1000294
breast carcinoma	3	MONDO:0004989	EFO:0000305
cutaneous melanoma	2	MONDO:0005012	EFO:0000389
diffuse large B-cell lymphoma	2	MONDO:0018905	EFO:0000403
sarcoma	2	MONDO:0005089	EFO:0000691
plasma cell myeloma	2	MONDO:0009693	EFO:0001378
metastatic melanoma	2	MONDO:0005191	EFO:0002617
anaplastic large cell lymphoma	2	MONDO:0020325	EFO:0003032
lung large cell carcinoma	2	MONDO:0003050	EFO:0003050
upper aerodigestive tract neoplasm	2	MONDO:0005398	EFO:0004284
lung adenocarcinoma	2	MONDO:0005061	EFO:0000571
rhabdomyosarcoma	2	MONDO:0005212	EFO:0002918
diffuse intrinsic pontine glioma	2	MONDO:0006033	EFO:1000026
fallopian tube neoplasm	2	MONDO:0021092	MONDO:0002158
ovarian cancer	2	MONDO:0008170	MONDO:0008170
lymphoma	2	MONDO:0005062	EFO:0000574
glioma	2	MONDO:0021042	MONDO:0021637
small cell lung carcinoma	1	MONDO:0008433	EFO:0000702
desmoplastic small round cell tumor	1	MONDO:0019373	EFO:1000895

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

Clinical trials

Total trials: 277.

Phase distribution

Phase	Trials
PHASE2	158
PHASE3	63
PHASE1	21
PHASE1/PHASE2	14
Not specified	11
PHASE4	5
PHASE2/PHASE3	3
EARLY_PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00372476	PHASE4	COMPLETED	Efficacy and Safety of Imatinib and Vinorelbine in Patients With Advanced Breast Cancer
NCT01196078	PHASE4	COMPLETED	A Study of Tarceva (Erlotinib) in Elderly Patients With Advanced Non-Small Cell Lung Cancer
NCT01848613	PHASE4	COMPLETED	Study of Patient Preference for Oral or Intravenous Vinorelbine in the Treatment of Advanced NSCLC
NCT02497118	PHASE4	COMPLETED	Recombinant Human Endostatin Combined With NP in Neoadjuvant Chemotherapy of Stage ⅢA NSCLC
NCT03270007	PHASE4	UNKNOWN	Research of Intensive Treatment in Hormone Receptor<10% and Human Epidermal Growth Factor Receptor-2 Negative Breast Cancer Patients With Positive Lymph Node Residual Disease After Neoadjuvant Chemotherapy
NCT02344472	PHASE3	ACTIVE_NOT_RECRUITING	Detect V / CHEVENDO (Chemo vs. Endo)
NCT02486718	PHASE3	ACTIVE_NOT_RECRUITING	Study to Assess Safety and Efficacy of Atezolizumab (MPDL3280A) Compared to Best Supportive Care Following Chemotherapy in Patients With Lung Cancer [IMpower010]
NCT02567435	PHASE3	ACTIVE_NOT_RECRUITING	Combination Chemotherapy With or Without Temsirolimus in Treating Patients With Intermediate Risk Rhabdomyosarcoma
NCT03456076	PHASE3	ACTIVE_NOT_RECRUITING	A Study Comparing Adjuvant Alectinib Versus Adjuvant Platinum-Based Chemotherapy in Patients With ALK Positive Non-Small Cell Lung Cancer
NCT04639986	PHASE3	ACTIVE_NOT_RECRUITING	Asian Study of Sacituzumab Govitecan (IMMU-132) in HR+/HER2- Metastatic Breast Cancer (MBC)
NCT05063786	PHASE3	ACTIVE_NOT_RECRUITING	Trastuzumab + Alpelisib +/- Fulvestrant vs Trastuzumab + CT in Patients With PIK3CA Mutated Previously Treated HER2+ Advanced BrEasT Cancer (ALPHABET)
NCT05104866	PHASE3	ACTIVE_NOT_RECRUITING	A Phase-3, Open-Label, Randomized Study of Dato-DXd Versus Investigator’s Choice of Chemotherapy (ICC) in Participants With Inoperable or Metastatic HR-Positive, HER2-Negative Breast Cancer Who Have Been Treated With One or Two Prior Lines of Systemic Chemotherapy (TROPION-Breast01)
NCT06081959	PHASE3	RECRUITING	Study of SKB264 for Locally Advanced, Recurrent or Metastatic HR+/HER2- Breast Cancer
NCT06268652	PHASE3	RECRUITING	Patient Derived Organoid-guided Personalized Treatment Versus Treatment of Physician’s Choice in Breast Cancer
NCT06343948	PHASE3	ACTIVE_NOT_RECRUITING	A Study Comparing BL-B01D1 With Chemotherapy of Physician’s Choice in Patients With Unresectable Locally Advanced, Recurrent, or Metastatic HR+HER2- Breast Cancer(PANKU-Breast01)
NCT06382142	PHASE3	ACTIVE_NOT_RECRUITING	A Study Comparing BL-B01D1 With Chemotherapy of Physician’s Choice in Patients With Unresectable Locally Advanced or Metastatic Triple-Negative Breast Cancer(PANKU-Breast02)
NCT06435429	PHASE3	RECRUITING	A Study Comparing the Efficacy and Safety of Zanidatamab to Trastuzumab, Each in Combination With Physician’s Choice Chemotherapy, for the Treatment of Participants With Metastatic HER2-positive Breast Cancer
NCT06459180	PHASE3	ACTIVE_NOT_RECRUITING	A Study to Compare Sacituzumab Tirumotecan (MK-2870) Monotherapy Versus Treatment of Physician’s Choice as Second-line Treatment for Participants With Recurrent or Metastatic Cervical Cancer (MK-2870-020/TroFuse-020/Gog-3101/ENGOT-cx20)
NCT06519370	PHASE3	ACTIVE_NOT_RECRUITING	FDA018-ADC vs Investigator’s Choice Chemotherapy to Treat Locally Advanced, Recurrent or Metastatic Triple-negative Breast Cancer
NCT06564844	PHASE3	ACTIVE_NOT_RECRUITING	A Phase III, Randomised Study of Adjuvant Dato-DXd in Combination With Rilvegostomig or Rilvegostomig Monotherapy Versus Standard of Care, Following Complete Tumour Resection, in Participants With Stage I Adenocarcinoma NSCLC Who Are ctDNA-positive or Have High-risk Pathological Features
NCT06632327	PHASE3	RECRUITING	Comparing Impact of Treatment Before or After Surgery in Patients With Stage II-IIIB Resectable Non-small Cell Lung Cancer
NCT06908304	PHASE3	RECRUITING	A Phase III Study With THIO + Cemiplimab vs Chemotherapy as 3rd Line Treatment in Advanced/Metastatic NSCLC
NCT06908993	PHASE3	RECRUITING	Tepotinib vs Standard Treatment in Patients With Advanced MET Exon 14 Mutated Non-Small Cell Lung Cancer Previously Treated
NCT07088263	PHASE3	RECRUITING	Adaptive Chemotherapy for the Treatment of Advanced Breast Cancer
NCT07461454	PHASE3	RECRUITING	YL202 Versus Treatment of Physician’s Choice in Patients With HR+/HER2- Breast Cancer
NCT00042315	PHASE3	TERMINATED	A Double-Blind, Randomized, Placebo-Controlled, Multicenter, Phase III Study of Tariquidar + Vinorelbine as First-Line Therapy in Non-Small Cell Lung Cancer (NSCLC)
NCT00088530	PHASE3	COMPLETED	BBR 2778 for Relapsed, Aggressive Non-Hodgkin’s Lymphoma (NHL)
NCT00128310	PHASE3	COMPLETED	Vinorelbine Versus Gemcitabine Plus Vinorelbine in Metastatic Breast Cancer Patients
NCT00146549	PHASE3	COMPLETED	Trastuzumab in Combination With Vinorelbine or Taxane-Based Chemotherapy in Patients With Metastatic Breast Cancer
NCT00148798	PHASE3	COMPLETED	Study of Cisplatin/Vinorelbine +/- Cetuximab as First-line Treatment of Advanced Non Small Cell Lung Cancer (FLEX)
NCT00169104	PHASE2/PHASE3	TERMINATED	Effects of Granulocyte Colony-stimulating Factor (G-CSF), Trastuzumab, and Vinorelbine on Immune Cell Function
NCT00193362	PHASE3	COMPLETED	Study of Paclitaxel, Carboplatin, and Gemcitabine Versus Gemcitabine and Vinorelbine for Non-Small Cell Lung Cancer
NCT00345059	PHASE3	TERMINATED	The DISTAL-2 Study: Docetaxel Alone or in Combination in Second-line Treatment of Advanced Non Small-Cell Lung Cancer
NCT00430001	PHASE3	UNKNOWN	Vinorelbine Plus (+) Trastuzumab vs Docetaxel Plus (+) Trastuzumab as 1 Line Treatment for HER2 Positive (+) Metastatic Breast Cancer
NCT00431106	PHASE3	COMPLETED	Vinorelbine and Gemcitabine Versus Capecitabine in Pretreated Metastatic Breast Cancer
NCT00441740	PHASE3	COMPLETED	Randomized Trial With Vinorelbine and Gemcitabine Versus Docetaxel and Gemcitabine in Patients With Non-Small Cell Lung Cancer
NCT00441922	PHASE3	COMPLETED	Trial of Docetaxel Versus Vinorelbine as 1st Line Treatment in Elderly Patients With Non-Small-Cell Lung Cancer (NSCLC)
NCT00499109	PHASE3	COMPLETED	Phase III of RRM1 & ERCC1 Directed Customized Chemotherapy for the Treatment of Patients With NSCLC
NCT00683514	PHASE3	COMPLETED	Oral Chemotherapy And Platinum With Radiotherapy Followed Or Not By Consolidation With The Same Chemotherapy In Locally Advanced Non Small Cell Lung Cancer
NCT00686959	PHASE3	COMPLETED	Chemotherapy and Radiation in Treating Participants With Stage 3 Non-Small Cell Lung Cancer

Clinical evidence (CIViC)

Variant × indication × effect (4 predictive associations from 4 curated evidence items):

Variant	Indication	Effect	Therapy	Level	CIViC
RRM1 Underexpression	Lung Non-small Cell Carcinoma	Sensitivity/Response	Paclitaxel + Vinorelbine + Gemcitabine	CIViC B	EID5599
SMARCA4 Underexpression	Lung Non-small Cell Carcinoma	Sensitivity/Response	Cisplatin + Vinorelbine	CIViC B	EID837
XRCC1 R194W	Lung Non-small Cell Carcinoma	Sensitivity/Response	Docetaxel + Gemcitabine + Vinorelbine	CIViC B	EID659
BRCA1 Expression	Malignant Mesothelioma	Sensitivity/Response	Vinorelbine	CIViC D	EID933

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).