topotecan   Click here for help

GtoPdb Ligand ID: 7101

Synonyms: Hycamtin® | SK-S-104864-A
Approved drug PDB Ligand
topotecan is an approved drug (EMA and FDA (1996))
Compound class: Synthetic organic
Comment: Topotecan is a semisynthetic analogue of the natural plant alkaloid camptothecin (PubChem CID 24360). Camptothecin was first isolated from the bark and stem of Camptotheca acuminata, the Chinsese happy tree. Topotecan is an anticancer drug which causes DNA strand breaks and leads to cell-cycle arrest and cell death.
Marketed formulations may contain topotecan hydrochloride (PubChem CID 60699).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 104.89
Molecular weight 421.16
XLogP 2.25
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCC1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
InChI InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
InChI Key UCFGDBYHRUNTLO-QHCPKHFHSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA and FDA (1996))
International Nonproprietary Names Click here for help
INN number INN
6783 topotecan
Synonyms Click here for help
Hycamtin® | SK-S-104864-A
Database Links Click here for help
CAS Registry No. 123948-87-8
ChEBI CHEBI:63632
ChEMBL Ligand CHEMBL84
DrugBank Ligand DB01030
DrugCentral Ligand 2707
GtoPdb PubChem SID 178103679
PubChem CID 60700
RCSB PDB Ligand TTC
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Wikipedia topotecan