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Compound Detail

CHEMBL1607

TOPOTECAN HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1.Cl

Basic Information

ChEMBL ID CHEMBL1607
Name TOPOTECAN HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key DGHHQBMTXTWTJV-BQAIUKQQSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL84
Active Moiety CHEMBL84

Known Names

Evotopin Hycamtin Nogitecan hydrochloride NSC-759263 Potactasol SK&F S-104864-A SK&F-S-104864-A SK&F-S-104864A SK-S-104864-A Topotecan (as hydrochloride) Topotecan actavis Topotecan eagle +4 more
11
Targets
35
Activities
2
Assay Types
1
PK Parameters
20
Publications
16
Known Names
20
Indications
1
Mechanisms

Molecular Properties

421.4
MW (Da)
1.85
ALogP
8
HBA
2
HBD
104.9
PSA (Ų)
0.49
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning First in Class
USAN Stem -tecan
USAN Year 1990

Extended Properties

Molecular Formula C23H24ClN3O5
MW 457.91
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness 0.90

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA topoisomerase I inhibitor INHIBITOR DNA topoisomerase 1

Indications

Carcinoma Carcinoma, Ovarian Epithelial Carcinoma, Small Cell Ovarian Neoplasms Ovarian Neoplasms Small Cell Lung Carcinoma Uterine Cervical Neoplasms Uterine Cervical Neoplasms Uterine Cervical Neoplasms Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Fallopian Tube Neoplasms Ganglioneuroblastoma Lung Neoplasms Neuroblastoma Peritoneal Neoplasms Rhabdomyosarcoma Sarcoma Sarcoma Breast Neoplasms

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States

Activity Summary

IC50 30 meas. best 8.84
EC50 5 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 8.84 7.0037 1.4 19
BJ
CHEMBL614358
EC50 7.7 6.515 19.8 4
NON-PROTEIN TARGET
CHEMBL3879801
IC50 6.92 6.0967 119.0 3
Jurkat
CHEMBL397
IC50 6.9 6.9 127.0 1
A-375
CHEMBL613859
IC50 6.79 6.79 162.0 1
HeLa
CHEMBL399
IC50 6.42 6.42 380.0 1
MDA-MB-231
CHEMBL400
IC50 6.33 6.33 473.0 1
Unchecked
CHEMBL612545
EC50 6.26 6.26 549.0 1
NCI-H460
CHEMBL396
IC50 6.21 6.21 610.0 1
DNA topoisomerase 1
CHEMBL1781
IC50 5.97 5.97 1080.0 1
KB
CHEMBL398
IC50 5.64 5.64 2282.0 1
HepG2
CHEMBL395
IC50 5.38 5.38 4208.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 2.25 /hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.44 nM 8.84 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 9.0 nM 8.05 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
Unchecked IC50 = 10.5 nM 7.98 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 13.6 nM 7.87 PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of ass... -
Unchecked IC50 = 17.9 nM 7.75 PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce... -
BJ EC50 = 19.8 nM 7.7 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Dose Response to Characterize Compound... -
Unchecked IC50 = 24.64 nM 7.61 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 25.03 nM 7.6 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (vi... -
Unchecked IC50 = 34.08 nM 7.47 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 34.16 nM 7.47 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 82.01 nM 7.09 PubChem BioAssay. Increased HeLa cells in S-phase-IC50. (Class of assay: confi... -
NON-PROTEIN TARGET IC50 = 119.0 nM 6.92 Cytotoxicity against human Caco2 cells after 24 hrs by MTT assay 24980118
Jurkat IC50 = 127.0 nM 6.9 Cytotoxicity against human Jurkat cells after 24 hrs by MTT assay 24980118
Unchecked IC50 = 133.7 nM 6.87 PubChem BioAssay. nuclear beta catenin stimulation in WNT3A conditioned C2C12 ce... -
BJ EC50 = 159.0 nM 6.8 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response HTS to Identify Compound... -
A-375 IC50 = 162.0 nM 6.79 Cytotoxicity against human A375 cells after 24 hrs by MTT assay 24980118
Unchecked IC50 = 176.8 nM 6.75 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 200.0 nM 6.7 PUBCHEM_BIOASSAY: Dose response confirmation of uHTS chemical inhibitors of T-ce... -
Unchecked IC50 = 232.6 nM 6.63 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
BJ EC50 = 246.0 nM 6.61 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Confirmation HTS to Identify Comp... -

Literature References

Data from ChEMBL 36 via Core Engine