VINORELBINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C45H54N4O8
Molecular Weight	778.9323
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C[C@@H]2CN(C1)CC3=C(NC4=C3C=CC=C4)[C@@](C2)(C(=O)OC)C5=CC6=C(C=C5OC)N(C)[C@@H]7[C@]68CCN9CC=C[C@](CC)([C@@H]89)[C@@H](OC(C)=O)[C@]7(O)C(=O)OC

InChI

InChIKey=GBABOYUKABKIAF-IELIFDKJSA-N

InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C45H54N4O8
Molecular Weight	778.9323
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10864196
Curator's Comment: Description was created based on several sources, including http://www.fda.gov/ohrms/dockets/ac/04/briefing/4021B1_10_Vinorelbine%20label.pdf | https://www.medicines.org.uk/emc/medicine/1604 | http://adisinsight.springer.com/drugs/800004195

Vinorelbine (trade name Navelbine) is a semi-synthetic vinca-alkaloid with a broad spectrum of anti-tumour activity. Vinorelbine is a mitotic spindle poison that impairs chromosomal segregation during mitosis. It blocks cells at G2/M. Microtubules (derived from polymers of tubulin) are the principal target of vinorelbine. Vinorelbine was developed by Pierre Fabre under licence from the CNRS in France. NAVELBINE (vinorelbine tartrate) as a single agent or in combination is indicated for the first line treatment of non small cell lung cancer and advanced breast cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10864196	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non-small cell lung cancer 211 Sources: http://www.fda.gov/ohrms/dockets/ac/04/briefing/4021B1_10_Vinorelbine%20label.pdf	Primary		Approved 8583	NAVELBINE Approved Use NAVELBINE (vinorelbine tartrate) is indicated as a single agent or in combination with cisplatin for the first-line treatment of ambulatory patients with unresectable, advanced nonsmall cell lung cancer (NSCLC). In patients with Stage IV NSCLC, NAVELBINE is indicated as a single agent or in combination with cisplatin. In Stage III NSCLC, NAVELBINE is indicated in combination with cisplatin. Launch Date 1994
Breast cancer 432 Sources: https://www.medicines.org.uk/emc/medicine/1604	Primary		Approved 8583	NAVELBINE Approved Use Oral NAVELBINE (vinorelbine tartrate) as a single agent or in combination for the first line treatment of stage 3 or 4 non small cell lung cancer, and treatment of advanced breast cancer stage 3 and 4 relapsing after or refractory to an anthracycline containing regimen. Launch Date 1994

C_max

Value	Dose	Co-administered	Analyte	Population
133.4 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11822766	80 mg/m² single, oral dose: 80 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
761.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11822766	25 mg/m² single, intravenous dose: 25 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1299 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11822766	80 mg/m² single, oral dose: 80 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1042 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11822766	25 mg/m² single, intravenous dose: 25 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
29.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11822766	80 mg/m² single, oral dose: 80 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
37.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11822766	25 mg/m² single, intravenous dose: 25 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
14.6% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/6a16e044-7d0e-44bd-8e7e-588a5063935f/spl-doc?hl=VINORELBINE			VINORELBINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 mg/m2 1 times / week multiple, intravenous Recommended Dose: 30 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 30 mg/m2, 1 times / week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf	unhealthy, 61 years (range: 32-79 years) Health Status: unhealthy Age Group: 61 years (range: 32-79 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf	DLT: Neutropenia, Neutropenia... Other AEs: Leukopenia, Leukopenia... Dose limiting toxicities: Neutropenia (grade 1, 80%) Neutropenia (grade 4, 29%) Other AEs: Leukopenia (grade 1, 81%) Leukopenia (grade 4, 12%) Thrombocytopenia (grade 1, 4%) Anemia (grade 1, 77%) Anemia (grade 3, 1%) AST increased (grade 3-4, 3%) Bilirubin increased (grade 3-4, 5%) Nausea (grade 3-4, 1%) Asthenia (grade 3-4, 5%) Constipation (grade 3-4, 2%) Injection site reaction (grade 3-4, 5%) Injection site pain (grade 3-4, 1%) Neuropathy peripheral (grade 3-4, 1%) Vomiting (grade 3-4, 1%) Diarrhea (grade 3-4, 1%) Alopecia (grade 3-4, 1%) Phlebitis (grade 3-4, 1%) Dyspnea (grade 3-4, 2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf
100 mg/m2 1 times / week multiple, oral MTD Dose: 100 mg/m2, 1 times / week Route: oral Route: multiple Dose: 100 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/11843245/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/11843245/	DLT: Neutropenia... Other AEs: Leukopenia, Vomiting... Dose limiting toxicities: Neutropenia (grade 3-4, 3 patients) Other AEs: Leukopenia (grade 3-4, 2 patients) Vomiting (grade 3-4, 2 patients) Diarrhoea (grade 1, 3 patients) Stomatitis (grade 3-4, 1 patient) Constipation (grade 3-4, 3 patients) Alopecia (grade 1-2, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11843245/
80 mg/m2 1 times / week multiple, oral RP2D Dose: 80 mg/m2, 1 times / week Route: oral Route: multiple Dose: 80 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/11843245/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/11843245/	DLT: Neutropenia, Neutropenia... Other AEs: Leukopenia, Vomiting... Dose limiting toxicities: Neutropenia (grade 3-4, 10 patients) Neutropenia (all grades, 11 patient) Other AEs: Leukopenia (grade 3-4, 7 patients) Vomiting (grade 3-4, 2 patients) Constipation (grade 3-4, 1 patient) Alopecia (grade 3-4, 1 patient) Anaemia (all grades, 9 patients) Leukopenia (all grades, 12 patients) Thrombocytopenia (all grades, 1 patient) Nausea (all grades, 13 patients) Vomiting (all grades, 11 patient) Diarrhoea (all grades, 9 patients) Stomatitis (all grades, 2 patients) Constipation (all grades, 8 patients) Alopecia (all grades, 9 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11843245/
25 mg/m2 1 times / week multiple, intravenous Recommended Dose: 25 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 25 mg/m2, 1 times / week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf	DLT: Neutropenia... Other AEs: Anemia, Leukopenia... Dose limiting toxicities: Neutropenia (grade 3-4, 82%) Other AEs: Anemia (grade 3-4, 24%) Leukopenia (grade 3-4, 58%) Thrombocytopenia (grade 3-4, 5%) Febrile neutropenia (grade 3-4, 11%) Blood creatinine increased (grade 3-4, 4%) Malaise and fatigue (grade 3-4, 12%) Vomiting (grade 3-4, 13%) Nausea (grade 3-4, 14%) Constipation (grade 3-4, 3%) Weight decreased (grade 3-4, 1%) Fever (grade 3-4, 2%) Hearing impaired (grade 3-4, 4%) Injection site reaction (grade 3-4, <1%) Diarrhea (grade 3-4, <3%) Paraesthesia (grade 3-4, <1%) Numbness (grade 3-4, 2%) Arthralgia (grade 3-4, <1%) Embolism and thrombosis (grade 3-4, 3%) Weakness (grade 3-4, <3%) Infection (grade 3-4, <6%) Respiratory tract infection (grade 3-4, <5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8/9 42 CYP2C19 2057 CYP1A2 2153 CYP2A6 879 CYP2E1 1060 CYP2B6 926 P-gp 1741 UGT 45	CYP3A 220 CYP3A5 446 CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729 CYP2J2 71 CYP3A7 109 CYP4A11 137 P-gp 2052 MRP2 252

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	likely
CYP2C19 2141	inhibitor 4027 Sources: https://mhraproducts4853.blob.core.windows.net/docs/97b9d8f32973422a554356404fb8d3d57f598315 Page: 8.0	likely
CYP2C8/9 42	inhibitor 4027 Sources: https://mhraproducts4853.blob.core.windows.net/docs/97b9d8f32973422a554356404fb8d3d57f598315, https://pubmed.ncbi.nlm.nih.gov/15601807/ Page: 8.0	likely
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no [IC50 >10 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11602674/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2005/P200500051/23012400_21100AMY00087_Q100_1.pdf#page=7 Page: (PMDA) 7	yes [IC50 10.6 uM]	unlikely (co-administration study) Comment: Coadministration of Vinorelbine significantly did not affect the exposure of Cyclophosphamide. Sources: https://www.pmda.go.jp/drugs/2005/P200500051/23012400_21100AMY00087_Q100_1.pdf#page=7 Page: (PMDA) 7
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8258200/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=071486221	yes [Ki 22 uM]
UGT 70	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12019202/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2J2 71	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP3A7 109	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP3A4 1946	substrate 4014 Sources: https://www.info.pmda.go.jp/go/interview/1/230124_4240407A1028_1_004_1F.pdf#page=23, https://pubmed.ncbi.nlm.nih.gov/23780963/ Page: (PMDA drug information) 23	yes [Km 2.63 uM]
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	yes [Km 3.64 uM]
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8258200/	yes
CYP3A 220	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf#page=14 Page: 14.0	yes
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22767610/	yes
P-gp 2052	substrate 4014 Sources: https://www.pdr.net/drug-summary/Navelbine-vinorelbine-tartrate-2360, https://pubmed.ncbi.nlm.nih.gov/11602674/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNTUzMDI1In19

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:480999	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:480999
eMolecules	36500497	https://www.emolecules.com/cgi-bin/more?vid=36500497
eMolecules	36754948	https://www.emolecules.com/cgi-bin/more?vid=36754948
MolPort	MolPort-006-823-869	https://www.molport.com/shop/molecule-link/MolPort-006-823-869
Selleck Chemicals	vinorelbine-navelbine	http://www.selleckchem.com/products/vinorelbine-navelbine.html
ZINC	ZINC000085536958	http://zinc15.docking.org/substances/ZINC000085536958

PubMed

Title	Date	PubMed
Vinorelbine, epirubicin, and methotrexate (VEM) as primary treatment in locally advanced breast cancer.	2001	11524553
Ongoing trials with trastuzumab in metastatic breast cancer.	2001	11521725
Spontaneous erections in a patient with erectile dysfunction after palliative chemotherapy for non-small cell lung cancer.	2001	11490213
Phase I-II vinorelbine (Navelbine) by continuous infusion in patients with metastatic breast cancer: cumulative toxicities limit dose escalation.	2001	11458813
A systematic overview of chemotherapy effects in non-small cell lung cancer.	2001	11441939
A systematic overview of chemotherapy effects in breast cancer.	2001	11441936
Activity and safety of vinorelbine combined with doxorubicin or fluorouracil as first-line therapy in advanced breast cancer: a stratified phase II study.	2001	11423674
Nonanthracycline containing docetaxel-based combinations in metastatic breast cancer.	2001	11346680
Vinorelbine-based regimens as salvage treatment in patients with advanced non-small cell lung cancer: two parallel multicenter phase II trials.	2001	11340375
[Subcutaneous inflammatory edema induced by MINE chemotherapy].	2001 Apr	11395653
Treatment of patients with metastatic germ cell tumors relapsing after high-dose chemotherapy.	2001 Apr	11374314
Phase III trial of cisplatin/gemcitabine with or without vinorelbine or paclitaxel in advanced non-small cell lung cancer.	2001 Apr	11372045
Acute respiratory failure caused by vinorelbine tartrate in a patient with non-small cell lung cancer.	2001 Aug	11518124
New cytotoxic agents and schedules for advanced breast cancer.	2001 Aug	11498829
Marked antitumor activity of a new potent acronycine derivative in orthotopic models of human solid tumors.	2001 Aug	11489841
Treatment of vinorelbine-associated tumor pain.	2001 Aug	11474276
The current status of docetaxel for advanced non-small cell lung cancer.	2001 Feb	11340898
Phase I dose-finding and pharmacokinetic study of docetaxel and vinorelbine as first-line chemotherapy for metastatic breast cancer.	2001 Jul	11521794
Recent advances in the chemotherapy of non-small cell lung cancer.	2001 Jul	11518741
Rationale for non-platinum chemotherapy in advanced NSCLC.	2001 Jul	11497229
Markedly diminished drug resistance-inducing properties of vinflunine (20',20'-difluoro-3',4'-dihydrovinorelbine) relative to vinorelbine, identified in murine and human tumour cells in vivo and in vitro.	2001 Jul	11488526
High-dose ifosfamide and vinorelbine as salvage therapy for relapsed or refractory Hodgkin's disease.	2001 Jul	11486403
A cost--utility analysis comparing second-line chemotherapy schemes in patients with metastatic breast cancer.	2001 Jul	11460000
Gemcitabine plus vinorelbine for the treatment of advanced non-small cell lung cancer.	2001 Jul	11435068
Mechanism of mitotic block and inhibition of cell proliferation by the semisynthetic Vinca alkaloids vinorelbine and its newer derivative vinflunine.	2001 Jul	11408618
Randomized phase III trial of paclitaxel plus carboplatin versus vinorelbine plus cisplatin in the treatment of patients with advanced non--small-cell lung cancer: a Southwest Oncology Group trial.	2001 Jul 1	11432888
Evaluating new treatments for advanced cancer.	2001 Jul 6	11437417
Linear immunoglobulin A bullous dermatosis induced by gemcitabine.	2001 Jul-Aug	11485141
Sequential docetaxel and vinorelbine for patients with advanced breast cancer previously treated with anthracyclines: a phase II study.	2001 Jul-Aug	11410787
Phase II study of vinorelbine in patients with androgen-independent prostate cancer.	2001 Jun	11484963
Cisplatin and vinorelbine in advanced and/or metastatic adenocarcinoma of the endometrium: a new highly active chemotherapeutic regimen.	2001 Jun	11484950
In vitro activity of vinorelbine on human leukemia cells.	2001 Jun	11450890
Review of two phase III randomized trials of single-agent docetaxel in previously treated advanced non--small cell lung cancer.	2001 Jun	11444253
Non-platinum based combination chemotherapy: phase I and II trials of docetaxel plus gemcitabine, vinorelbine, or irinotecan.	2001 Jun	11441410
Phase III randomized trial of docetaxel in combination with cisplatin or carboplatin or vinorelbine plus cisplatin in advanced non--small cell lung cancer: interim analysis.	2001 Jun	11441409
Paclitaxel and docetaxel enhance the metabolism of doxorubicin to toxic species in human myocardium.	2001 Jun	11410484
Results of a phase III prospective, randomised trial, comparing mitoxantrone and vinorelbine (MV) in combination with standard FAC/FEC in front-line therapy of metastatic breast cancer.	2001 Jun	11378344
Importance of surgery as salvage treatment after high dose chemotherapy failure in germ cell tumors.	2001 Jun	11371882
Oral fluoropyrimidines among the new drugs for patients with metastatic breast cancer.	2001 Jun 1	11384089
Heterogeneity of proteinkinase C activity and PKC-zeta expression in clinical breast carcinomas.	2001 Mar	11467396
[Cisplatin and vinorelbine therapy of previously treated advanced breast cancer (preliminary studies)].	2001 Mar	11398513
Correspondence re: Cicchetti S, Jemec B, Gault DT: two case reports of vinorelbine extravasation: management and review of the literature. Tumori, 86: 289-292, 2000.	2001 Mar-Apr	11401208
[Non-small cell lung cancer with liver metastasis responsive to gemcitabine--a case report].	2001 May	11383223
[Non-small-cell lung cancer (NSCLC) in an elderly patient--a case of squamous cell carcinoma successfully treated with chemotherapy using vinorelbine].	2001 May	11383221
Gemcitabine and vinorelbine as second-line therapy in non-small-cell lung cancer after prior treatment with taxane+platinum-based regimens.	2001 May	11334721
Clinical activity of trastuzumab and vinorelbine in women with HER2-overexpressing metastatic breast cancer.	2001 May 15	11352965
Multi-institutional phase I/II trial of oral bexarotene in combination with cisplatin and vinorelbine in previously untreated patients with advanced non-small-cell lung cancer.	2001 May 15	11352954
Advances in chemotherapy for small cell lung cancer: single-agent activity of newer agents.	2001 May-Jun	11419031
Vinflunine, a second generation novel Vinca Alkaloid with a distinctive pharmacological profile, now in clinical development and prospects for future mitotic blockers.	2001 Sep	11472262
Modifications in the "upper" velbenamine part of the Vinca alkaloids have major implications for tubulin interacting activities.	2001 Sep	11472261

Patents

Sample Use Guides

In Vivo Use Guide

NAVELBINE (vinorelbine tartrate) for intravenous injections is indicated for the treatment of non-small cell lung cancer. Single-Agent NAVELBINE (vinorelbine tartrate): The usual initial dose of single-agent NAVELBINE is 30 mg/m2 administered weekly. Oral NAVELBINE is indicated for the treatment of non-small cell lung cancer and advanced breast cancer. As a single agent, the recommended regimen is: First three administrations 60mg/m² of body surface area, administered once weekly. Subsequent administrations Beyond the third administration, it is recommended to increase the dose of Navelbine to 80mg/m² once weekly except in those patients for whom the neutrophil count dropped once below 500/mm3 or more than once between 500 and 1000/mm3 during the first three administrations at 60mg/m².

Route of Administration: Other

In Vitro Use Guide

IC(50) values for inhibition of HeLa cell proliferation for vinorelbine was 1.25 nM, similar to the concentrations that induced mitotic block at the metaphase/anaphase transition (3.8 nM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:25 GMT 2025`
Record UNII	Q6C979R91Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VINORELBINE

Official Name

English

VINORELBINE [HSDB]

Preferred Name

English

VINORELBINE TARTRATE IMPURITY J [EP IMPURITY]

Common Name

English

NAVELBIN

Common Name

English

Vinorelbine [WHO-DD]

Common Name

English

VINORELBINE [ORANGE BOOK]

Common Name

English

vinorelbine [INN]

Common Name

English

ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 4-(ACETYLOXY)-6,7-DIDEHYDRO-15-((2R,6R,8S)-4-ETHYL-1,3,6,7,8,9-HEXAHYDRO-8-(METHOXYCARBONYL)-2,6-METHANO-2H-AZECINO(4,3-B)INDOL-8-YL)-3-HYDROXY-16-METHOXY-1-METHYL-, METHYL ESTER, (2.BETA.,3.BETA.,4.BETA.,5.ALPHA.,12R,

Systematic Name

English

4-DEOXY-3,4-DIDEHYDROVINCALEUKOBLASTINE

Systematic Name

English

C'-NORVINCALEUKOBLASTINE, 3',4'-DIDEHYDRO-4'-DEOXY-

Systematic Name

English

NSC-760087

Code

English

VINORELBINE [MI]

Common Name

English

VINORELBINE [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007780