vinblastine   Click here for help

GtoPdb Ligand ID: 6851

Synonyms: 29060-LE | Velban® | Velbe® | vincaleucoblastin | vincaleukoblastine
Approved drug PDB Ligand
vinblastine is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: A pan tubulin inhibitor. A chemical analogue of vincristine (from Catharanthus roseus, also known as Vinca rosea). There is some ambiguity surrounding the exact stereochemistry of vinblastine. The chirality shown here corresponds to the PubChem entry linked to in the table above. However, bioactivity data for the compound is also listed against CID 241903, and some of the links in the table above refer to this chiral specification or others. Marketed formulations contain vinblastine sulfate (PubChem CID 5388983).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: vinblastine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 154.1
Molecular weight 810.42
XLogP 4.73
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES COc1cc2N(C)C3C4(c2cc1C1(CC2CN(CCc5c1[nH]c1c5cccc1)CC(C2)(O)CC)C(=O)OC)CCN1C4C(C(C3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
Isomeric SMILES COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
InChI InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1
InChI Key JXLYSJRDGCGARV-CFWMRBGOSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names Click here for help
INN number INN
1101 vinblastine
Synonyms Click here for help
29060-LE | Velban® | Velbe® | vincaleucoblastin | vincaleukoblastine
Database Links Click here for help
CAS Registry No. 865-21-4
ChEBI CHEBI:27375
ChEMBL Ligand CHEMBL159
DrugBank Ligand DB00570
DrugCentral Ligand 2823
GtoPdb PubChem SID 178103457
PubChem CID 13342
RCSB PDB Ligand VLB
Search Google for chemical match using the InChIKey JXLYSJRDGCGARV-CFWMRBGOSA-N
Search Google for chemicals with the same backbone JXLYSJRDGCGARV
Search PubMed clinical trials vinblastine
Search PubMed titles vinblastine
Search PubMed titles/abstracts vinblastine
Search UniChem for chemical match using the InChIKey JXLYSJRDGCGARV-CFWMRBGOSA-N
Search UniChem for chemicals with the same backbone JXLYSJRDGCGARV
Wikipedia Vinblastine