General
Preferred name
TOPOTECAN
Synonyms
TOPOTECAN HYDROCHLORIDE ()
SKF 104864A ()
NSC 609669 ()
Topotecan HCl ()
NSC609699 ()
Nogitecan HCl ()
SKFS 104864A ()
Hycamtin ()
Topotecan (HCl) ()
Topotecan HCl (Hycamtin) ()
Hycamptin ()
Hycamptamine ()
9-Dimethylaminomethyl-10-hydroxycamptothecin, HCl salt ()
SKF-S 104864-A ()
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline- 3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, monohydrochloride, (4S)- ()
Topetecan ()
Topotecan (Hydrochloride) ()
SKF 104864A (Hydrochloride) ()
NSC 609669 (Hydrochloride) ()
Topotecan (NSC609699) HCl ()
Nogitecan HCl, SKFS 104864A,Hycamtin, NSC 609699 ()
NSC609699,Nogitecan,SKFS 104864A ()
NSC-641007 ()
Potactasol ()
Nogitecan ()
NSC-609699 ()
Ff-10850 (liposomal topotecan) ()
SKF-104864 ()
Topotecan ()
Topotecan actavis ()
NSC-759263 ()
SK&F S-104864-A ()
Topotecan (as hydrochloride) ()
Evotopin ()
SK&F-S-104864A ()
SK-S-104864-A ()
Topotecan hospira ()
Topotecan teva ()
Nogitecan hydrochloride ()
Topotecan-d6 ()
P&D ID
PD003417
CAS
123948-87-8
119413-54-6
1044904-10-0
Tags
nuisance
natural product
probe
drug
available
Approved by
EMA
FDA
First approval
1996
Drug Status
investigational
approved
withdrawn
Drug indication
Ovarian cancer
Small-cell lung cancer
Antineoplastic (DNA topoisomerase I Inhibitor)
Solid tumour/cancer
Max Phase
Phase 4
Probe info
Probe type
calculated probe
Probe sources
Probe Miner (suitable probes)
Probe targets
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA Topotecan has the same mechanism of action as irinotecan and is believed to exert its cytotoxic effects during the S-phase of DNA synthesis. Topoisomerase I relieves torsional strain in DNA by inducing reversible single strand breaks. Topotecan binds to the topoisomerase I-DNA complex and prevents religation of these single strand breaks. This ternary complex interferes with the moving replication fork, which leads to the induction of replication arrest and lethal double-stranded breaks in DNA. As mammalian cells cannot efficiently repair these double strand breaks, the formation of this ternary complex eventually leads to apoptosis (programmed cell death).; ; Topotecan mimics a DNA base pair and binds at the site of DNA cleavage by intercalating between the upstream (−1) and downstream (+1) base pairs. Intercalation displaces the downstream DNA, thus preventing religation of the cleaved strand. By specifically binding to the enzyme–substrate complex, Topotecan acts as an uncompetitive inhibitor.
DESCRIPTION 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). (GtoPdb)
DESCRIPTION inhibitor of topoisomerase I (Informer Set)
DESCRIPTION Inhibitor of UCHL5 and USP14 (Tocris Bioactive Compound Library)
Cell lines
78
Organisms
1
Compound Sets
35
AdooQ Bioactive Compound Library
A10939
Cayman Chemical Bioactives
14129
29082
ChEMBL Approved Drugs
CHEMBL84
CHEMBL1607
ChEMBL Drugs
CHEMBL84
CHEMBL1607
Drug Repurposing Hub
DrugBank
DB01030
DrugBank Approved Drugs
DB01030
DrugCentral
2707
DrugCentral Approved Drugs
2707
DrugMAP
DMP6G8T
DMAE6LK
DrugMAP Approved Drugs
DMP6G8T
DMAE6LK
Enamine BioReference Compounds
Guide to Pharmacology
7101
Informer Set
44580
LINCS compound set
10278-999
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL84
CHEMBL1607
Mcule NIBR MoA Box Subset
MCULE-8592965711
MedChem Express Bioactive Compound Library
HY-13768A
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
7M7YKX2N15
NIH Approved Oncology Drugs
580652
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
Pandemic Response Box
Prestwick Chemical Library
Probe Miner (suitable probes)
Q99814/321984
ReFrame library
Selleckchem Bioactive Compound Library
topotecan
Topotecan-Hydrochloride
TargetMol Bioactive Compound Library
T1174
The Spectrum Collection
Tocris Bioactive Compound Library
4562
Withdrawn 2.0
EMA46
ZINC Tool Compounds
ZINC000001611274
External IDs
82
Properties
(calculated by RDKit )
Molecular Weight
421.16
Hydrogen Bond Acceptors
8
Hydrogen Bond Donors
2
Rotatable Bonds
3
Ring Count
5
Aromatic Ring Count
3
cLogP
1.85
TPSA
104.89
Fraction CSP3
0.35
Chiral centers
1.0
Largest ring
6.0
QED
0.49
Structural alerts
1
Intercalation
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
Target
TOP1
Autophagy
Topo I (DU-145 Luc cells)
Topo I (MCF-7 Luc cells)
TOP1, TOP1MT
Topoisomerase
Apoptosis related,Autophagy,Topoisomerase
Compound status
FDA
Pathway
Cell Cycle/DNA Damage
DNA Damage/DNA Repair
Apoptosis
Primary Target
DNA Topoisomerases
MOA
Inhibitor
DNA Topoisomerase I Inhibitors
Topoisomerase inhibitor
Member status
member
Indication
small cell lung cancer, cervical cancer
ATC
L01XX17
Biosynthetic Origin
Alkaloid
Therapeutic Indication
Anticancer
Therapeutic Class
Anticancer Agents
Source data