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 that is 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 CID provided on the Summary tab. However, bioactivity data for the compound is also listed against CID 241903, and some of the external resource links refer to this chiral specification or others. Marketed formulations contain vinblastine sulfate (PubChem CID 5388983).
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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
DrugBank Ligand DB00570
DrugCentral Ligand 2823
GtoPdb PubChem SID 178103457
PubChem CID 13342
Search Google for chemical match using the InChIKey JXLYSJRDGCGARV-CFWMRBGOSA-N
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UniChem Compound Search for chemical match using the InChIKey JXLYSJRDGCGARV-CFWMRBGOSA-N
UniChem Connectivity Search for chemical match using the InChIKey JXLYSJRDGCGARV-CFWMRBGOSA-N
Wikipedia Vinblastine