Compound Detail

CHEMBL84

TOPOTECAN

💊 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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL84
Name	TOPOTECAN
Phase	Approved
Structure Type	MOL
InChI Key	UCFGDBYHRUNTLO-QHCPKHFHSA-N
Therapeutic	✓ Yes

Known Names

Ff-10850 (liposomal topotecan) Hycamptamine Hycamptin Nogitecan NSC-609699 NSC-641007 SK&F-104864 SKF-104864 Topotecan Topotecane

Targets

338

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

421.4

MW (Da)

1.85

ALogP

HBA

HBD

104.9

PSA (Å²)

0.49

QED

Ro5 Violations

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 Natural Product First in Class

USAN Stem	-tecan
USAN Year	1990

Extended Properties

Molecular Formula	C23H23N3O5
MW	421.45
Aromatic Rings	3
Heavy Atoms	31
NP-Likeness	0.90

Indications

Carcinoma, Non-Small-Cell Lung Ganglioneuroblastoma Lung Neoplasms Neoplasms Neoplasms Neuroblastoma Ovarian Neoplasms Ovarian Neoplasms Ovarian Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Retinoblastoma Small Cell Lung Carcinoma Uterine Cervical Neoplasms Uterine Cervical Neoplasms Uterine Cervical Neoplasms Brain Neoplasms Breast Neoplasms Carcinoma, Ovarian Epithelial Central Nervous System Neoplasms Colonic Neoplasms

ATC Classification

L01CE01

topotecan

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 332 meas. best 8.92

EC50 5 meas. best 7.92

Kd 1 meas. best 7.58

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Bel-7402 CHEMBL614279	IC50	8.92	6.3533	1.2	9
HCT-8 CHEMBL613510	IC50	8.82	6.7188	1.5	8
MCF7 CHEMBL387	IC50	8.74	6.3026	1.8	23
SW-620 CHEMBL612262	IC50	8.49	8.49	3.2	1
A549 CHEMBL392	IC50	8.49	6.61	3.2	34
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.4	6.2378	4.0	40
BGC-823 CHEMBL614526	IC50	8.37	6.565	4.3	4
KETR3 CHEMBL614637	IC50	8.31	8.31	4.9	1
LOX IMVI CHEMBL614096	IC50	8.3	8.3	5.0	1
A2780 CHEMBL614004	IC50	8.22	6.08	6.0	11
NCI-H69 CHEMBL614805	IC50	8.22	7.74	6.0	3
ADMET CHEMBL612558	IC50	8.1	6.712	8.0	5
Hep 3B2 CHEMBL4296437	IC50	8.1	8.1	7.9	1
LNCaP CHEMBL612518	IC50	8.05	8.05	9.0	1
LoVo CHEMBL614721	IC50	7.94	7.184	11.6	5
HL-60 CHEMBL383	IC50	7.92	7.6	12.0	2
RPMI 8402 CHEMBL612517	IC50	7.92	7.805	12.0	4
Hypoxia-inducible factor 1-alpha CHEMBL4261	EC50	7.92	7.92	12.0	1
A-375 CHEMBL613859	IC50	7.89	7.89	13.0	1
COR-L23 CHEMBL613854	IC50	7.88	7.79	13.2	2
NCI-H460 CHEMBL396	IC50	7.8	6.2838	16.0	13
MOLT-4 CHEMBL614177	IC50	7.72	7.72	19.0	1
RPMI-8226 CHEMBL614882	IC50	7.68	7.68	21.0	1
DNA topoisomerase 1 CHEMBL1781	IC50	7.68	5.9846	21.0	13
HT-29 CHEMBL384	IC50	7.6	6.3825	25.0	12
SK-BR-3 CHEMBL613834	IC50	7.58	6.315	26.0	2
DNA topoisomerase 1 CHEMBL1781	Kd	7.58	7.58	26.5	1
NCI-H128 CHEMBL614771	IC50	7.51	7.51	31.0	1
MKN-45 CHEMBL614354	IC50	7.42	7.42	38.0	1
P388 CHEMBL389	IC50	7.4	7.36	40.0	5
DU-145 CHEMBL613508	IC50	7.4	6.44	40.0	3
KB 3-1 CHEMBL614590	IC50	7.4	6.776	40.0	5
Tumor cell line CHEMBL614310	IC50	7.4	7.4	40.0	1
SK-OV-3 CHEMBL614925	IC50	7.36	7.3467	44.0	3
PC-3 CHEMBL390	IC50	7.35	6.4557	45.0	7
A-427 CHEMBL614515	IC50	7.31	7.31	49.0	1
DNA topoisomerase 1 CHEMBL1781	EC50	7.27	7.21	54.0	2
WiDr CHEMBL614647	IC50	7.25	7.25	56.0	1
L1210 CHEMBL386	IC50	7.25	6.944	56.0	5
U-87 MG CHEMBL614247	IC50	7.22	7.22	60.0	1
Hypoxia-inducible factor 1-alpha CHEMBL4261	IC50	7.22	7.22	60.0	1
HepG2 CHEMBL395	IC50	7.22	6.1488	60.0	8
KB CHEMBL398	IC50	7.21	6.8627	62.0	11
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	EC50	7.15	7.15	71.3	1
MDA-MB-435 CHEMBL614697	IC50	7.1	6.4725	79.0	4
SW480 CHEMBL612544	IC50	7.05	7.05	90.0	1
HCT-116 CHEMBL394	IC50	7.05	6.2388	88.9	8
SK-N-SH CHEMBL614924	IC50	7.03	7.03	93.0	1
MDA-MB-231 CHEMBL400	IC50	7.0	6.4329	100.0	7
T47D CHEMBL614361	IC50	6.98	6.98	104.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	3.24	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	0.625	mL.min-1.kg-1	Rattus norvegicus
CL	5.3	mL.min-1.kg-1	Rattus norvegicus
CL	0.4867	mL.min-1.kg-1	Rattus norvegicus
CL	0.4583	mL.min-1.kg-1	Rattus norvegicus
CL	40.15	mL.min-1.kg-1	Rattus norvegicus
F	32.0	%	Homo sapiens
Fu	0.65	-	Homo sapiens
Fu	0.747	-	Rattus norvegicus
MRT	2.3	hr	Homo sapiens
T1/2	0.38	hr	-
T1/2	0.4817	hr	-
t1/2	-	-	-
T1/2	2.3	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Bel-7402	IC50	=	1.2	nM	8.92	Cytotoxicity against human Bel7402 cells after 96 hrs by MTT assay	15165144
HCT-8	IC50	=	1.5	nM	8.82	Cytotoxicity against human HCT8 cells after 96 hrs by MTT assay	15165144
MCF7	IC50	=	1.8	nM	8.74	Cytotoxicity against human MCF7 cells after 96 hrs by MTT assay	15165144
SW-620	IC50	=	3.2	nM	8.49	Cytotoxic potentiation of Topotecan (TP) by the compound in human colon carcinom...	12408707
A549	IC50	=	3.2	nM	8.49	Cytotoxicity against human A549 cells after 96 hrs by MTT assay	15165144
A549	IC50	=	3.2	nM	8.49	Antiproliferative activity against human A549 cells assessed as reduction in cel...	38421819
NON-PROTEIN TARGET	IC50	=	4.0	nM	8.4	Cytotoxicity against human MESSA cells after 72 hrs by alamar blue assay	21341674
BGC-823	IC50	=	4.3	nM	8.37	Cytotoxicity against human BGC823 cells after 96 hrs by MTT assay	15165144
KETR3	IC50	=	4.9	nM	8.31	Cytotoxicity against human Ketr3 cells after 96 hrs by MTT assay	15165144
LOX IMVI	IC50	=	5.0	nM	8.3	Cytotoxicity was determined in vitro in LOX cells (melanoma) of human tumor cell...	7853331
A549	IC50	=	5.0	nM	8.3	Antitumor activity against human A549 cells after 4 hrs by MTT assay	18207748
A2780	IC50	=	6.0	nM	8.22	Cytotoxicity against human A2780 cells overexpressing alpha5beta3 integrin asses...	22959246
NCI-H69	IC50	=	6.0	nM	8.22	Cytotoxicity against human H69 cells after 72 hrs by alamar blue assay	21341674
A549	IC50	=	7.0	nM	8.15	Antiproliferative activity against human A549 cells after 96 hrs by MTT assay	27871039
Hep 3B2	IC50	=	7.9	nM	8.1	Cytotoxicity against human Hep3B cells assessed as growth inhibition measured af...	31881457
ADMET	IC50	=	8.0	nM	8.1	Cytotoxicity against mouse bone marrow cell by CFU-GM assay	21341674
LNCaP	IC50	=	9.0	nM	8.05	Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay	21341674
LoVo	IC50	=	11.6	nM	7.94	Cytotoxic potentiation of Topotecan (TP) by the compound in (human colorectal ca...	12408707
RPMI 8402	IC50	=	12.0	nM	7.92	Cytotoxic activity against human lymphoblast tumor cell line RPMI8402 after 4 da...	12747798
Hypoxia-inducible factor 1-alpha	EC50	=	12.0	nM	7.92	Inhibition of human HIF1alpha-mediated transcription expressed in human U251 cel...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	89
21051535	10.1124/dmd.110.034629	ADMET	21
16472241	10.2174/1570163043334794	Hepatotoxicity	18
8576914	10.1021/jm950507y	Mus musculus	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
11052801	10.1021/jm000944z	NON-PROTEIN TARGET	14
21440338	10.1016/j.ejmech.2011.03.001	PC-3	13
11563925	10.1021/jm0108092	NCI-H460	12
7853331	10.1021/jm00003a001	Mus musculus	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
27871039	10.1016/j.ejmech.2016.11.013	A549	10
34008967	10.1021/acs.jmedchem.1c00318	MCF7	9
16913706	10.1021/jm060285b	MKN-28	9
19715319	10.1021/jm900469e	HT-29	9
35728506	10.1016/j.ejmech.2022.114530	MGC-803	9
11052801	10.1021/jm000944z	NCI-H460	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
35728506	10.1016/j.ejmech.2022.114530	SGC-7901	8
37099835	10.1016/j.ejmech.2023.115366	RKO	7
11563925	10.1021/jm0108092	ADMET	7

Data from ChEMBL 36 via Core Engine