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

[H][C@@]12N3CC[C@@]14C5=CC(=C(OC)C=C5N(C)[C@@]4([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]6(C[C@H]7CN(CC(CC)=C7)CC8=C6NC9=C8C=CC=C9)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	7 / 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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non-small cell lung cancer 206 Sources: http://www.fda.gov/ohrms/dockets/ac/04/briefing/4021B1_10_Vinorelbine%20label.pdf	Primary		Approved 8429	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 434 Sources: https://www.medicines.org.uk/emc/medicine/1604	Primary		Approved 8429	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
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

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) n = 143 Health Status: unhealthy Condition: metastatic NSCLC Age Group: 61 years (range: 32-79 years) Sex: M+F Population Size: 143 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 n = 6 Health Status: unhealthy Condition: advanced breast cancer Age Group: adult Sex: F Population Size: 6 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 n = 13 Health Status: unhealthy Condition: advanced breast cancer Age Group: adult Sex: F Population Size: 13 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 Co-administed with:: cisplatin(100 mg/m^2; 1/month) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf	unhealthy n = 212 Health Status: unhealthy Condition: NSCLC Population Size: 212 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 1737 inhibitor 1587	substrate 1037	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8/9 44 CYP2C19 1478 CYP1A2 1524 CYP2A6 707 CYP2E1 882 CYP2B6 810 P-gp 1461 UGT 35	CYP3A 191 CYP3A5 395 CYP1A1 349 CYP1A2 1054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667 CYP2J2 56 CYP3A7 110 CYP4A11 119 P-gp 1537 MRP2 205

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	likely
CYP2C19 1553	inhibitor 3277 Sources: https://mhraproducts4853.blob.core.windows.net/docs/97b9d8f32973422a554356404fb8d3d57f598315 Page: 8.0	likely
CYP2C8/9 44	inhibitor 3277 Sources: https://mhraproducts4853.blob.core.windows.net/docs/97b9d8f32973422a554356404fb8d3d57f598315, https://pubmed.ncbi.nlm.nih.gov/15601807/ Page: 8.0	likely
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no [IC50 >10 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11602674/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1MzAyNSJ9fQ%3D%3D	no
CYP3A4 1925	inhibitor 3277 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 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/8258200/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=071486221	yes [Ki 22 uM]
UGT 59	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12019202/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP2J2 56	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP3A7 110	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	unlikely
CYP3A4 1737	substrate 3367 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 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23780963/	yes [Km 3.64 uM]
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8258200/	yes
CYP3A 191	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020388s037lbl.pdf#page=14 Page: 14.0	yes
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22767610/	yes
P-gp 1537	substrate 3367 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 1647	inhibitor 1626 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
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
eMolecules	36500497	https://www.emolecules.com/cgi-bin/more?vid=36500497
eMolecules	36754948	https://www.emolecules.com/cgi-bin/more?vid=36754948

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
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
Chemotherapy of metastatic breast cancer: what to expect in 2001 and beyond.	2001	11306725
[Subcutaneous inflammatory edema induced by MINE chemotherapy].	2001 Apr	11395653
Phase III trial of cisplatin/gemcitabine with or without vinorelbine or paclitaxel in advanced non-small cell lung cancer.	2001 Apr	11372045
Preoperative chemotherapy for lung cancer does not increase surgical morbidity.	2001 Apr	11308144
Phase II study of vinorelbine in the treatment of platinum-resistant ovarian carcinoma.	2001 Apr	11277650
Sensitive determination of vinorelbine and its metabolites in human serum using liquid chromatography-electrospray mass spectrometry.	2001 Apr 5	11334329
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
The current status of docetaxel for advanced non-small cell lung cancer.	2001 Feb	11340898
[Medical treatment of pulmonary neoplasms].	2001 Feb	11294106
Challenging the platinum combinations: docetaxel (Taxotere) combined with gemcitabine or vinorelbine in non-small cell lung cancer.	2001 Feb	11284620
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
High-dose ifosfamide and vinorelbine as salvage therapy for relapsed or refractory Hodgkin's disease.	2001 Jul	11486403
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
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
Review of two phase III randomized trials of single-agent docetaxel in previously treated advanced non--small cell lung cancer.	2001 Jun	11444253
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
Importance of surgery as salvage treatment after high dose chemotherapy failure in germ cell tumors.	2001 Jun	11371882
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
Typhlitis (neutropenic enterocolitis) after a single dose of vinorelbine.	2001 Mar	11320673
Prevention of vinorelbine phlebitis with cimetidine. A two-step design study.	2001 Mar	11305068
Treatment of elderly patients with non-small-cell lung cancer.	2001 Mar	11301849
Gemcitabine for the treatment of non-small-cell lung cancer.	2001 Mar	11301846
Triplet combination chemotherapy and targeted therapy regimens.	2001 Mar	11301845
Gemcitabine and nonplatinum combinations in non-small-cell lung cancer.	2001 Mar	11301844
Gemcitabine and vinorelbine as first-line chemotherapy for advanced non-small cell lung cancer: a phase II trial.	2001 Mar	11290433
Regional plus systemic chemotherapy: an effective treatment in recurrent non-small cell lung cancer.	2001 Mar	11289757
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
Gemcitabine and vinorelbine as second-line therapy in non-small-cell lung cancer after prior treatment with taxane+platinum-based regimens.	2001 May	11334721
Carboplatin and vinorelbine in untreated locally advanced and metastatic non-small cell lung cancer.	2001 May	11325488
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
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 `Fri Dec 15 15:57:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:57:17 GMT 2023`
Record UNII	Q6C979R91Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VINORELBINE

Official 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 [HSDB]

Common Name

English

VINORELBINE [MI]

Common Name

English

VINORELBINE [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007780