U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of VINORELBINE

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Vinorelbine, epirubicin, and methotrexate (VEM) as primary treatment in locally advanced breast cancer.
2001
Ongoing trials with trastuzumab in metastatic breast cancer.
2001
Spontaneous erections in a patient with erectile dysfunction after palliative chemotherapy for non-small cell lung cancer.
2001
Treatment of patients with metastatic germ cell tumors relapsing after high-dose chemotherapy.
2001 Apr
Acute respiratory failure caused by vinorelbine tartrate in a patient with non-small cell lung cancer.
2001 Aug
New cytotoxic agents and schedules for advanced breast cancer.
2001 Aug
Marked antitumor activity of a new potent acronycine derivative in orthotopic models of human solid tumors.
2001 Aug
Phase I dose-finding and pharmacokinetic study of docetaxel and vinorelbine as first-line chemotherapy for metastatic breast cancer.
2001 Jul
Recent advances in the chemotherapy of non-small cell lung cancer.
2001 Jul
Rationale for non-platinum chemotherapy in advanced NSCLC.
2001 Jul
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
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: intravenous, oral
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).
Name Type Language
VINORELBINE
HSDB   INN   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
VINORELBINE [ORANGE BOOK]
Common Name English
VINORELBINE [INN]
Common Name English
VINORELBINE [HSDB]
Common Name English
VINORELBINE [WHO-DD]
Common Name English
VINORELBINE [MI]
Common Name English
VINORELBINE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007780
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
NDF-RT N0000007780
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
NDF-RT N0000175612
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
WHO-ATC L01CA04
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
LIVERTOX 1031
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
WHO-VATC QL01CA04
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
Code System Code Type Description
CAS
71486-22-1
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
EPA CompTox
71486-22-1
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
MERCK INDEX
M11457
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL553025
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
RXCUI
39541
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY RxNorm
DRUG BANK
DB00361
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
EVMPD
SUB00069MIG
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
PUBCHEM
5311497
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY SWITZERF
LactMed
71486-22-1
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
IUPHAR
7105
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
INN
6054
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
NCI_THESAURUS
C1275
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
WIKIPEDIA
VINORELBINE
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
MESH
C030852
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY
HSDB
71486-22-1
Created by admin on Tue Mar 06 11:21:54 UTC 2018 , Edited by admin on Tue Mar 06 11:21:54 UTC 2018
PRIMARY