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)- ()
SKF 104864A (Hydrochloride) ()
NSC 609669 (Hydrochloride) ()
Topetecan ()
Topotecan (Hydrochloride) ()
Topotecan (NSC609699) HCl ()
Nogitecan HCl, SKFS 104864A,Hycamtin, NSC 609699 ()
NSC609699,Nogitecan,SKFS 104864A ()
NSC-609699 ()
Topotecane ()
NSC-641007 ()
SKF-104864 ()
Ff-10850 (liposomal topotecan) ()
Topotecan ()
SK-S-104864-A ()
Evotopin ()
Topotecan teva ()
SK&F S-104864-A ()
SK&F-S-104864A ()
Topotecan hospira ()
Topotecan actavis ()
NSC-759263 ()
Nogitecan hydrochloride ()
Potactasol ()
Topotecan (as hydrochloride) ()
Topotecan-d6 ()
P&D ID
PD003417
CAS
123948-87-8
119413-54-6
1044904-10-0
Tags
available
nuisance
drug
probe
Approved by
FDA
EMA
First approval
1996
Drug indication
Small-cell lung cancer
Ovarian cancer
Solid tumour/cancer
Antineoplastic (DNA topoisomerase I Inhibitor)
Drug Status
withdrawn
approved
investigational
Max Phase
4.0
Probe info
Probe type
calculated probe
Probe sources
Probe Miner (suitable probes)
Probe targets
EPAS1
Probe control
Probe control not defined
Orthogonal probes
3
Similar probes
0
No structurally similar probes found
Structure
PD003417
TOPOTECAN
EPAS1
nuisance approved
RO5
MW
421.16
HBA
8
HBD
2
RB
3
LOGP
1.85
42
37
1
26
10
Probe scores
P&D probe-likeness score
0%
0%
0%
0%
0%
10%
0%
10%
P&D probe-likeness EPAS1
53%
Probe Miner Score EPAS1
Structure formats
SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1
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
InChIkey
UCFGDBYHRUNTLO-QHCPKHFHSA-N
MOL
TOPOTECAN RDKit 2D 31 35 0 0 0 0 0 0 0 0999 V2000 4.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2135 5.3237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.2054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1568 7.6972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5271 8.3073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 9.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4704 10.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6272 12.1725 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5864 13.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 12.7826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0542 10.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2110 11.9009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2677 9.5275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1110 8.0357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7406 7.4256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5838 5.9338 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2135 5.3237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 6 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 13 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 20 25 1 0 25 26 1 0 25 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 10 3 1 0 31 12 1 0 14 9 1 0 31 17 1 0 29 19 1 0 M END > <ID> PD003417 > <Name> TOPOTECAN
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)
Protein targets
26
7.15
EPAS1,HIF1A Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha
0
1
6.6
7.57
HIF1A Hypoxia-inducible factor 1-alpha CELL-BASED 2.6x
11
3
6.6
LMNA Prelamin-A/C BIOCHEM 1x
8
1
6.23
TOP2A,TOP2B DNA topoisomerase II
0
1
5.97
5.88
TOP1 DNA topoisomerase 1 inhibitor
1
13
5.89
SLC47A1 Multidrug and toxin extrusion protein 1
1
1
5.82
CYP3A4 Cytochrome P450 3A4
7
1
5.67
ORF 73
0
1
5.55
RMLC dTDP-4-dehydrorhamnose 3,5-epimerase
0
1
5.5
LEF Lethal factor
1
1
5.44
LANA1 Protein LANA1
0
1
5.43
KEAP1,NFE2L2 Keap1/Nrf2
0
1
5.32
RORC Nuclear receptor ROR-gamma
3
1
5.25
CASP1 Caspase-1
10
1
5.25
CASP7 Caspase-7
6
1
5.2
BRCA1 Breast cancer type 1 susceptibility protein
27
1
5.16
GLF UDP-galactopyranose mutase
0
1
5.07
SLC47A2 Multidrug and toxin extrusion protein 2
1
1
4.9
HBB Hemoglobin subunit beta
9
1
4.9
KMT2A,MEN1 Menin/Histone-lysine N-methyltransferase MLL
0
1
4.55
MAPT Microtubule-associated protein tau
3
1
4.55
IMPA1 Inositol monophosphatase 1
1
1
4.35
KMT2A Histone-lysine N-methyltransferase 2A
5
1
4.21
SLC22A2 Solute carrier family 22 member 2
5
1
TOP1MT DNA topoisomerase I, mitochondrial inhibitor
0
0
EPAS1 Endothelial PAS domain-containing protein 1
0
Target pathways
94
Abacavir transmembrane transport
R-HSA-2161517
SLC22A2
Activation of AMPK downstream of NMDARs
R-HSA-9619483
MAPT
Activation of caspases through apoptosome-mediated cleavage
R-HSA-111459
CASP7
Aflatoxin activation and detoxification
R-HSA-5423646
CYP3A4
Apoptotic cleavage of cellular proteins
R-HSA-111465
CASP7
Aspirin ADME
R-HSA-9749641
CYP3A4
Atorvastatin ADME
R-HSA-9754706
CYP3A4
Biosynthesis of maresin-like SPMs
R-HSA-9027307
CYP3A4
Breakdown of the nuclear lamina
R-HSA-352238
LMNA
Caspase-mediated cleavage of cytoskeletal proteins
R-HSA-264870
MAPT
CASP7
Cellular response to hypoxia
R-HSA-1234174
HIF1A
Chaperone Mediated Autophagy
R-HSA-9613829
HBB
Circadian Clock
R-HSA-400253
HIF1A
Cytoprotection by HMOX1
R-HSA-9707564
HBB
Defective DNA double strand break response due to BARD1 loss of function
R-HSA-9699150
BRCA1
Defective DNA double strand break response due to BRCA1 loss of function
R-HSA-9663199
BRCA1
Defective HDR through Homologous Recombination Repair (HRR) due to PALB2 loss of BRCA1 binding function
R-HSA-9704331
BRCA1
Defective HDR through Homologous Recombination Repair (HRR) due to PALB2 loss of BRCA2/RAD51/RAD51C binding function
R-HSA-9704646
BRCA1
Defective homologous recombination repair (HRR) due to BRCA1 loss of function
R-HSA-9701192
BRCA1
Depolymerization of the Nuclear Lamina
R-HSA-4419969
LMNA
Deregulated CDK5 triggers multiple neurodegenerative pathways in Alzheimer's disease models
R-HSA-8862803
LMNA
Erythrocytes take up carbon dioxide and release oxygen
R-HSA-1237044
HBB
Erythrocytes take up oxygen and release carbon dioxide
R-HSA-1247673
HBB
Factors involved in megakaryocyte development and platelet production
R-HSA-983231
HBB
Formation of WDR5-containing histone-modifying complexes
R-HSA-9772755
KMT2A
G2/M DNA damage checkpoint
R-HSA-69473
BRCA1
HDR through Homologous Recombination (HRR)
R-HSA-5685942
BRCA1
HDR through Single Strand Annealing (SSA)
R-HSA-5685938
BRCA1
Heme signaling
R-HSA-9707616
HBB
Homologous DNA Pairing and Strand Exchange
R-HSA-5693579
BRCA1
Impaired BRCA2 binding to PALB2
R-HSA-9709603
BRCA1
Impaired BRCA2 binding to RAD51
R-HSA-9709570
BRCA1
Initiation of Nuclear Envelope (NE) Reformation
R-HSA-2995383
LMNA
Interleukin-1 processing
R-HSA-448706
CASP1
Interleukin-37 signaling
R-HSA-9008059
CASP1
Interleukin-4 and Interleukin-13 signaling
R-HSA-6785807
RORC
HIF1A
KEAP1-NFE2L2 pathway
R-HSA-9755511
BRCA1
Late endosomal microautophagy
R-HSA-9615710
HBB
Meiotic recombination
R-HSA-912446
BRCA1
Meiotic synapsis
R-HSA-1221632
BRCA1
LMNA
Metalloprotease DUBs
R-HSA-5689901
BRCA1
Na+/Cl- dependent neurotransmitter transporters
R-HSA-442660
SLC22A2
Neddylation
R-HSA-8951664
BRCA1
HIF1A
Neurotransmitter clearance
R-HSA-112311
SLC22A2
Neutrophil degranulation
R-HSA-6798695
HBB
NOD1/2 Signaling Pathway
R-HSA-168638
CASP1
Nonhomologous End-Joining (NHEJ)
R-HSA-5693571
BRCA1
Norepinephrine Neurotransmitter Release Cycle
R-HSA-181430
SLC22A2
NOTCH1 Intracellular Domain Regulates Transcription
R-HSA-2122947
HIF1A
Nuclear Envelope Breakdown
R-HSA-2980766
LMNA
Nuclear Receptor transcription pathway
R-HSA-383280
RORC
Organic cation transport
R-HSA-549127
SLC22A2
Oxygen-dependent proline hydroxylation of Hypoxia-inducible Factor Alpha
R-HSA-1234176
HIF1A
Phase I - Functionalization of compounds
R-HSA-211945
CYP3A4
PKMTs methylate histone lysines
R-HSA-3214841
KMT2A
PKR-mediated signaling
R-HSA-9833482
MAPT
Prednisone ADME
R-HSA-9757110
CYP3A4
Presynaptic phase of homologous DNA pairing and strand exchange
R-HSA-5693616
BRCA1
Processing of DNA double-strand break ends
R-HSA-5693607
BRCA1
PTK6 Expression
R-HSA-8849473
HIF1A
PTK6 promotes HIF1A stabilization
R-HSA-8857538
HIF1A
Purinergic signaling in leishmaniasis infection
R-HSA-9660826
CASP1
Pyroptosis
R-HSA-5620971
CASP1
Recruitment and ATM-mediated phosphorylation of repair and signaling proteins at DNA double strand breaks
R-HSA-5693565
BRCA1
Regulation of gene expression by Hypoxia-inducible Factor
R-HSA-1234158
HIF1A
Regulation of MITF-M-dependent genes involved in DNA replication, damage repair and senescence
R-HSA-9825895
BRCA1
Regulation of TP53 Activity through Phosphorylation
R-HSA-6804756
BRCA1
Resolution of D-loop Structures through Holliday Junction Intermediates
R-HSA-5693568
BRCA1
Resolution of D-loop Structures through Synthesis-Dependent Strand Annealing (SDSA)
R-HSA-5693554
BRCA1
RUNX1 regulates genes involved in megakaryocyte differentiation and platelet function
R-HSA-8936459
KMT2A
RUNX1 regulates transcription of genes involved in differentiation of HSCs
R-HSA-8939236
KMT2A
RUNX3 Regulates Immune Response and Cell Migration
R-HSA-8949275
RORC
SARS-CoV-1 activates/modulates innate immune responses
R-HSA-9692916
CASP1
Scavenging of heme from plasma
R-HSA-2168880
HBB
Signaling by BRAF and RAF1 fusions
R-HSA-6802952
LMNA
SMAC (DIABLO) binds to IAPs
R-HSA-111463
CASP7
SMAC(DIABLO)-mediated dissociation of IAP:caspase complexes
R-HSA-111464
CASP7
SMAC, XIAP-regulated apoptotic response
R-HSA-111469
CASP7
STAT3 nuclear events downstream of ALK signaling
R-HSA-9701898
HIF1A
SUMOylation of DNA damage response and repair proteins
R-HSA-3108214
BRCA1
SUMOylation of DNA replication proteins
R-HSA-4615885
TOP1
Synthesis of IP2, IP, and Ins in the cytosol
R-HSA-1855183
IMPA1
The AIM2 inflammasome
R-HSA-844615
CASP1
The IPAF inflammasome
R-HSA-844623
CASP1
The NLRP3 inflammasome
R-HSA-844456
CASP1
TP53 Regulates Transcription of Caspase Activators and Caspases
R-HSA-6803207
CASP1
TP53 Regulates Transcription of DNA Repair Genes
R-HSA-6796648
BRCA1
Transcriptional Regulation by E2F6
R-HSA-8953750
BRCA1
Transcriptional regulation of granulopoiesis
R-HSA-9616222
KMT2A
Transport of bile salts and organic acids, metal ions and amine compounds
R-HSA-425366
SLC47A1
SLC47A2
Ub-specific processing proteases
R-HSA-5689880
HIF1A
Uptake and function of anthrax toxins
R-HSA-5210891
LEF
XBP1(S) activates chaperone genes
R-HSA-381038
LMNA
Xenobiotics
R-HSA-211981
CYP3A4
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2009 7-Cycloalkylcamptothecin derivatives: Preparation and biological evaluation.
Li M, Jin W et al. Bioorg. Med. Chem. Lett.
2009 Synthesis and antiproliferative evaluation of 6-arylindeno[1,2-c]quinoline derivatives.
Tseng CH, Chen YL et al. Bioorg. Med. Chem.
2009 Cytotoxicity and TOP1-targeting activity of 8- and 9-amino derivatives of 5-butyl- and 5-(2-N,N-dimethylamino)ethyl-5H-dibenzo[c,h][1,6]naphthyridin-6-ones.
Sharma L, Tsai YC et al. Eur. J. Med. Chem.
2009 Semisynthesis, biological activity, and molecular modeling studies of C-ring-modified camptothecins.
Samori C, Guerrini A et al. J. Med. Chem.
2008 New homocamptothecins: synthesis, antitumor activity, and molecular modeling.
Miao Z, Sheng C et al. Bioorg. Med. Chem.
2008 Novel hexacyclic camptothecin derivatives. Part 1: synthesis and cytotoxicity of camptothecins with an A-ring fused 1,3-oxazine ring.
Wang S, Li Y et al. Bioorg. Med. Chem. Lett.
2008 E-ring-modified 7-oxyiminomethyl camptothecins: Synthesis and preliminary in vitro and in vivo biological evaluation.
Giannini G, Marzi M et al. Bioorg. Med. Chem. Lett.
2008 Semi-synthesis and biological activity of gamma-lactones analogs of camptothecin.
Li M, Tang W et al. Bioorg. Med. Chem. Lett.
2008 Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors.
Dallavalle S, Gattinoni S et al. Bioorg. Med. Chem. Lett.
2008 Synthesis and cytotoxic activity of new 9-substituted camptothecins.
Dallavalle S, Rocchetta DG et al. Bioorg. Med. Chem. Lett.
2008 Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents.
Feng W, Satyanarayana M et al. Bioorg. Med. Chem.
2008 11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents.
Feng W, Satyanarayana M et al. Bioorg. Med. Chem.
2007 Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives.
Nacro K, Zha CC et al. Bioorg. Med. Chem.
2007 Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the Fungus Phellinus igniarius.
Wang Y, Shang XY et al. J. Nat. Prod.
2006 Mono-, Bi-, and triphenanthrenes from the tubers of Cremastra appendiculata.
Xue Z, Li S et al. J. Nat. Prod.
2006 A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes.
Lin P, Li S et al. J. Nat. Prod.
2006 Synthesis and cytotoxic activity of polyamine analogues of camptothecin.
Dallavalle S, Giannini G et al. J. Med. Chem.
2005 Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex.
Staker BL; Feese MD et al.
2005 Synthesis and antitumor activity of 7-ethyl-9-alkyl derivatives of camptothecin.
Gao H, Zhang X et al. Bioorg. Med. Chem. Lett.
2005 5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.
Ruchelman AL, Houghton PJ et al. J. Med. Chem.
2004 Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius.
Mo S, Wang S et al. J. Nat. Prod.
2004 Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity.
Ruchelman AL, Zhu S et al. Bioorg. Med. Chem. Lett.
2004 Design, synthesis, and evaluation of 3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-ones as inhibitors of poly(ADP-ribose) polymerase.
Tikhe JG, Webber SE et al. J. Med. Chem.
2004 Laurenditerpenol, a new diterpene from the tropical marine alga Laurenciaintricata that potently inhibits HIF-1 mediated hypoxic signaling in breast tumor cells.
Mohammed KA, Hossain CF et al. J. Nat. Prod.
2004 Imatinib mesylate is a potent inhibitor of the ABCG2 (BCRP) transporter and reverses resistance to topotecan and SN-38 in vitro.
Houghton PJ, Germain GS et al. Cancer Res.
2003 Synthesis and pharmacological evaluation of novel non-lactone analogues of camptothecin.
Hautefaye P, Cimetiere B et al. Bioorg. Med. Chem. Lett.
2003 Regioselective synthesis and cytotoxicities of camptothecin derivatives modified at the 7-, 10- and 20-positions.
Pan XD, Han R et al. Bioorg. Med. Chem. Lett.
2003 Nitro and amino substitution in the D-ring of 5-(2-dimethylaminoethyl)- 2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-ones: effect on topoisomerase-I targeting activity and cytotoxicity.
Singh SK, Ruchelman AL et al. J. Med. Chem.
2002 Novel angular benzophenazines: dual topoisomerase I and topoisomerase II inhibitors as potential anticancer agents.
Vicker N, Burgess L et al. J. Med. Chem.
2002 Novel tricyclic poly(ADP-ribose) polymerase-1 inhibitors with potent anticancer chemopotentiating activity: design, synthesis, and X-ray cocrystal structure.
Canan Koch SS, Thoresen LH et al. J. Med. Chem.
2002 Diaza- and triazachrysenes: potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435.
Ruchelman AL, Singh SK et al. Bioorg. Med. Chem. Lett.
2001 Synthesis and biological evaluation of novel A-ring modified hexacyclic camptothecin analogues.
Kim DK; Ryu DH et al.
2001 Novel cytotoxic 7-iminomethyl and 7-aminomethyl derivatives of camptothecin.
Dallavalle S, Ferrari A et al. Bioorg. Med. Chem. Lett.
2000 Novel C-ring analogues of 20(S)-camptothecin. Part 3: synthesis and their in vitro cytotoxicity of A-, B- and C-ring analogues.
Subrahmanyam D, Sarma VM et al. Bioorg. Med. Chem. Lett.
2000 Resistance-modifying agents. 9. Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase.
White AW, Almassy R et al. J. Med. Chem.
2000 Novel 7-substituted camptothecins with potent antitumor activity.
Dallavalle S, Delsoldato T et al. J. Med. Chem.
1999 Novel C-ring analogues of 20(S)-camptothecin-part-2: synthesis and in vitro cytotoxicity of 5-C-substituted 20(S)-camptothecin analogues.
Subrahmanyam D, Venkateswarlu A et al. Bioorg. Med. Chem. Lett.
1998 Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogues.
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1997 BN 80245: An E-ring modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities
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1996 Water soluble inhibitors of topoisomerase I: quaternary salt derivatives of camptothecin.
Lackey K; Sternbach DD et al.
1995 Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topoisomerase I.
Luzzio MJ; Besterman JM et al.
1995 Synthesis, topoisomerase I inhibitory activity, and in vivo evaluation of 11-azacamptothecin analogs.
Uehling DE; Nanthakumar SS et al.
1993 Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
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1991 Synthesis of water-soluble (aminoalkyl)camptothecin analogues: inhibition of topoisomerase I and antitumor activity.
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DrugMatrix in vitro pharmacology data (dataset)
AID 1695
AID 435023
AID 1224863
PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease: Purified N370S Glucocerebrosidase. (Class of assay: confirmatory) [Related pubchem assays: 2101 ] AID 2597
Cell lines
80
8.49
SW-620
8.31
KETR3
8.3
LOX IMVI
8.22
NCI-H69
8.1
Hep 3B2
8.05
LNCaP
8
DU-145
8
HOP-62
8
UACC-62
7.72
MOLT-4
7.7
COR-L23
7.7
RPMI 8402
7.7
SN12C
7.7
BJ
7.68
RPMI-8226
7.66
HCT-8
7.51
NCI-H128
7.42
MKN-45
7.4
ACHN
7.4
Tumor cell line
7.36
SK-OV-3
7.35
P388
7.31
A-427
7.28
HL-60
7.25
WiDr
7.22
U-87 MG
7.21
PC-3
7.15
NCI/ADR-RES
7.11
A2780
7.11
BGC-823
7.1
SF-268
7.05
SW480
7.03
SK-N-SH
7
L1210
6.98
T47D
6.92
LoVo
6.9
Jurkat
6.85
SK-MEL-2
6.82
SK-VLB
6.8
Panel (56 tumour cell lines)
6.8
IGROV-1
6.79
A-375
6.7
OVCAR-8
6.66
OVCAR-3
6.58
MCF7
6.52
AGS
6.47
KB VCR R
6.43
U-251
6.42
HeLa
6.4
MDA-MB-435
6.38
RKO
6.36
KB 3-1
6.33
MDA-MB-231
6.3
HT-1080
6.21
NCI-H460
6.21
BXPC-3
6.13
MGC-803
6.04
K562
6.01
HCT-116
6
Malme-3M
5.97
GES1
5.96
A549
5.96
U-937
5.89
WISH
5.85
M21
5.82
THP-1
5.7
A498
5.64
KB
5.48
HT-29
5.38
HepG2
5.38
SGC-7901
5.37
MRC5
5.24
C6
5.15
Bel-7402
5.05
SK-BR-3
4.97
HGC-27
4.96
NCI-H1299
4.93
SMMC-7721
4.93
QGY-7703
4.58
HEL
Organisms
1
5.42
Oncorhynchus gorbuscha
Compound Sets
37
A Collection of Useful Nuisance Compounds (CONS) for Interrogation of Bioassay Integrity
AdooQ Bioactive Compound Library
A10939
Cayman Chemical Bioactives
14129
29082
ChEMBL Approved Drugs
CHEMBL84
CHEMBL1607
ChEMBL Drugs
CHEMBL84
CHEMBL1607
CZ-OPENSCREEN Bioactive Library
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
Available from
12
AdooQ Bioactive Compound Library
A10939
Cayman Chemical Bioactives
14129
29082
Enamine BioReference Compounds
Mcule
MCULE-8930146194
MCULE-8592965711
MCULE-3610169892
MCULE-7254920975
Mcule NIBR MoA Box Subset
MCULE-8592965711
MedChem Express Bioactive Compound Library
HY-13768A
MolPort
MolPort-003-850-580
Molport-003-850-580
MolPort-003-666-754
Molport-003-666-754
MolPort-003-850-581
Molport-003-850-581
Prestwick Chemical Library
Selleckchem Bioactive Compound Library
topotecan
Topotecan-Hydrochloride
TargetMol Bioactive Compound Library
T1174
The Spectrum Collection
Tocris Bioactive Compound Library
4562
External IDs
87
ChEMBL CHEMBL84 CHEMBL1607
GtoPdb 7101
PubChem 60700 11972519 60699 57525346 25241339 168319588
ZINC ZINC000001611274
ACToR 123948-87-8 119413-54-6
BindingDB 50034026 50008935
Brenda 154401 4873 153416 230151 230152 139356
ChEBI 63632
ChemicalBook CB1339804 CB3361775
ChemSpider 54705 54704
ClinicalTrials.gov TOPOTECAN HYDRO... HYCAMPTIN SKF-104864 HYCAMTIN NOGITECAN HYDRO... NSC-609699 TOPOTECAN TOPOTECAN HOSPIRA POTACTASOL
COCONUT CNP0074922.1
CompTox DTXSID3042685 DTXSID1045952 DTXSID20649450
DailyMed TOPOTECAN TOPOTECAN HYDRO...
DrugBank DB01030
DrugCentral 2707
eMolecules 29542583 31590322 36366781 2724680 27524294
FDA SRS 7M7YKX2N15 956S425ZCY
GSRS b9e2e3a6-357a-4... f0d39c4b-548e-4...
HMDB HMDB15164 HMDB0015164 HMDB0301823
IBM NIH C491BF277F0255B...
KEGG C11158
LINCS LSM-5662
Mcule MCULE-8930146194 MCULE-8592965711 MCULE-3610169892 MCULE-7254920975
MolPort MolPort-003-850-580 Molport-003-850-580 MolPort-003-666-754 Molport-003-666-754 MolPort-003-850-581 Molport-003-850-581
NIH NCC SAM001246651
Nikkaji J2.256.757H J2.256.755A J362.027A
PDB TTC
PharmGKB PA451729
PubChem DOTF 12014351
PubChem TPS 14904851 14807035 14858018 14808962 57587883
Reactome 54705 54704
RxNorm HYCAMTIN TOPOTECAN HYDRO... TOPOTECAN
Selleck Topotecan-Hydro...
SureChEMBL SCHEMBL3836 SCHEMBL7247
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
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
Nuisance MOA
Intercalation
Targets
Hypoxia-inducible factor 1 alpha DNA topoisomerase I
Source data