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Compound Detail

CHEMBL481

IRINOTECAN
💊 Approved Drug
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💊 Approved Drug
CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL481
Name IRINOTECAN
Phase Approved
Structure Type MOL
InChI Key UWKQSNNFCGGAFS-XIFFEERXSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL837

Known Names

Biotecan Irinophore c Irinotecan NSC-728073
78
Targets
231
Activities
2
Assay Types
15
PK Parameters
20
Publications
4
Known Names
20
Indications

Molecular Properties

586.7
MW (Da)
4.09
ALogP
9
HBA
1
HBD
114.2
PSA (Ų)
0.36
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

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

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -tecan
USAN Year 1995

Extended Properties

Molecular Formula C33H38N4O6
MW 586.69
Aromatic Rings 3
Heavy Atoms 43
NP-Likeness 0.26

Indications

Neoplasms Neoplasms Brain Neoplasms Brain Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Hepatocellular Carcinoma, Neuroendocrine Carcinoma, Pancreatic Ductal Cholangiocarcinoma Cholangiocarcinoma Choroid Plexus Neoplasms Colonic Neoplasms Colonic Neoplasms Colonic Neoplasms Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Esophageal Neoplasms

ATC Classification

L01CE02
irinotecan
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 226 meas. best 11.0
Ki 5 meas. best 7.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI-H446
CHEMBL612440
 IC50 11.0 9.205 0.0 4
ADMET
CHEMBL612558
 IC50 9.0 7.98 1.0 2
A-375
CHEMBL613859
 IC50 8.4 8.4 4.0 1
PC-3
CHEMBL390
 IC50 8.4 6.915 4.0 2
HCT-116
CHEMBL394
 IC50 8.36 5.7423 4.4 13
SW-620
CHEMBL612262
 IC50 8.29 6.9475 5.1 4
T84
CHEMBL613531
 IC50 8.16 7.04 6.9 2
LNCaP
CHEMBL612518
 IC50 8.05 8.05 9.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 5.795 10.0 10
NCI-H460
CHEMBL396
 IC50 7.82 6.575 15.0 4
NCI-H69
CHEMBL614805
 IC50 7.66 7.66 22.0 1
Acetylcholinesterase
CHEMBL4780
 Ki 7.58 7.58 26.4 1
IGROV-1
CHEMBL613984
 IC50 7.52 7.52 30.0 1
A549
CHEMBL392
 IC50 7.5 5.3626 32.0 23
HL-60
CHEMBL383
 IC50 7.5 6.435 32.0 2
HeLa
CHEMBL399
 IC50 7.5 6.1325 32.0 4
Acetylcholinesterase
CHEMBL220
 Ki 7.3 7.3 50.5 1
SW480
CHEMBL612544
 IC50 7.16 5.4983 70.0 12
SK-MEL-2
CHEMBL614917
 IC50 7.0 7.0 100.0 1
MCF7
CHEMBL387
 IC50 6.8 5.4213 160.0 24
DU-145
CHEMBL613508
 IC50 6.7 5.666 200.0 5
Malme-3M
CHEMBL614021
 IC50 6.7 6.7 200.0 1
NCI-H1299
CHEMBL612255
 IC50 6.66 5.5513 220.0 8
HT-29
CHEMBL384
 IC50 6.66 5.32 220.0 9
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 6.66 6.66 217.0 1
H69AR
CHEMBL5209893
 IC50 6.6 6.6 250.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 6.34 6.34 461.0 1
NCI-H526
CHEMBL2366102
 IC50 6.31 6.31 490.0 1
RPMI 8402
CHEMBL612517
 IC50 6.24 6.24 570.0 1
RKO
CHEMBL614879
 IC50 6.16 5.685 700.0 2
LS174T
CHEMBL614097
 IC50 6.16 6.05 700.0 2
Unchecked
CHEMBL612545
 IC50 6.13 4.9173 740.0 11
HepG2
CHEMBL395
 IC50 6.05 5.388 900.0 5
NB-4
CHEMBL614188
 IC50 6.0 6.0 1000.0 1
CAPAN-1
CHEMBL614536
 IC50 5.95 5.885 1121.0 2
MDA-MB-435
CHEMBL614697
 IC50 5.94 5.3033 1140.0 3
L1210
CHEMBL386
 IC50 5.92 5.92 1200.0 2
MIA PaCa-2
CHEMBL614725
 IC50 5.88 5.88 1329.0 1
L02
CHEMBL4296457
 IC50 5.88 5.265 1305.0 2
Muscarinic acetylcholine receptor M4
CHEMBL1821
 IC50 5.81 5.81 1556.0 1
Acetylcholinesterase
CHEMBL220
 IC50 5.74 5.74 1827.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
 IC50 5.68 5.3833 2100.0 3
786-0
CHEMBL613102
 IC50 5.65 5.65 2250.0 1
NCI-H82
CHEMBL2366077
 IC50 5.65 5.65 2260.0 1
Solute carrier family 22 member 2
CHEMBL1743122
 IC50 5.57 5.57 2700.0 1
HCT-15
CHEMBL612263
 IC50 5.57 5.57 2700.0 1
NCI-H211
CHEMBL4523578
 IC50 5.55 5.55 2810.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 IC50 5.5 5.5 3171.0 1
NCI-H1975
CHEMBL614348
 IC50 5.47 5.07 3410.0 2
NCI-H2228
CHEMBL1075536
 IC50 5.46 5.46 3430.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.0 mL.min-1.kg-1 Homo sapiens
CL 3.9 mL.min-1.kg-1 Canis lupus familiaris
CL 7.0 mL.min-1.kg-1 Homo sapiens
CL 7.4 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Macaca
CL 37.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.49 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Fu 0.51 - Homo sapiens
MRT 8.3 hr Homo sapiens
MRT 9.1 hr Homo sapiens
T1/2 9.0 hr Homo sapiens
T1/2 0.75 hr Rattus norvegicus
T1/2 5.2 hr Homo sapiens
T1/2 56.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI-H446 IC50 = 0.01 nM 11.0 Antiproliferative activity against human NCI-H446 cells assessed as inhibition o... 35932565
NCI-H446 IC50 = 0.13 nM 9.89 Antiproliferative activity against etoposide/cisplatin combination-resistant hum... 35932565
NCI-H446 IC50 = 0.15 nM 9.82 Antiproliferative activity against Irinotecan-resistant human NCI-H446 cells ass... 35932565
ADMET IC50 = 1.0 nM 9.0 Cytotoxicity against mouse bone marrow cell by CFU-GM assay 21341674
A-375 IC50 = 4.0 nM 8.4 Cytotoxicity against human A375 cells after 72 hrs by alamar blue assay 21341674
PC-3 IC50 = 4.0 nM 8.4 Cytotoxicity against human PC3 cells after 72 hrs by alamar blue assay 21341674
HCT-116 IC50 = 4.4 nM 8.36 Anticancer activity against human HCT-116 cells assessed as inhibition of cell p... 33221063
SW-620 IC50 = 5.1 nM 8.29 Anticancer activity against human SW-620 cells assessed as inhibition of cell pr... 33221063
T84 IC50 = 6.9 nM 8.16 Anticancer activity against human T84 cells assessed as inhibition of cell proli... 33221063
LNCaP IC50 = 9.0 nM 8.05 Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay 21341674
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Cytotoxicity against human MESSA cells after 72 hrs by alamar blue assay 21341674
NCI-H460 IC50 = 15.0 nM 7.82 Cytotoxicity against human H460 cells after 72 hrs by alamar blue assay 21341674
NCI-H69 IC50 = 22.0 nM 7.66 Cytotoxicity against human H69 cells after 72 hrs by alamar blue assay 21341674
NON-PROTEIN TARGET IC50 = 22.0 nM 7.66 Cytotoxicity against human MES-SA/Dx5 cells overexpressing MDR1 after 72 hrs by ... 21341674
Acetylcholinesterase Ki = 26.4 nM 7.58 Inhibition of Torpedo californica AChE 18479118
NCI-H460 IC50 = 27.0 nM 7.57 Cytotoxicity against human H460 cells after 72 hrs by alamar blue assay in prese... 21341674
IGROV-1 IC50 = 30.0 nM 7.52 Cytotoxicity against human IGROV1 cells after 72 hrs by alamar blue assay 21341674
A549 IC50 = 32.0 nM 7.5 Antiproliferative activity against human A549 cells after 72 hrs by MTT assay 30660827
A549 IC50 = 32.0 nM 7.5 Cytotoxicity against human A549 cells assessed as reduction in cell viability me... 38421819
HL-60 IC50 = 32.0 nM 7.5 Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay 30660827

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
32352777 10.1021/acs.jmedchem.0c00305 ADMET 33
37413981 10.1021/acs.jmedchem.3c00476 ADMET 28
35231830 10.1016/j.ejmech.2022.114196 MCF7 22
35231830 10.1016/j.ejmech.2022.114196 SW480 21
31972391 10.1016/j.ejmech.2020.112067 SK-OV-3 19
14971908 10.1021/jm031072e Mus musculus 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
35231830 10.1016/j.ejmech.2022.114196 NCI-H1299 16
21051535 10.1124/dmd.110.034629 ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
33221063 10.1016/j.bmc.2020.115849 SW-620 13
24583355 10.1016/j.ejmech.2014.02.018 NON-PROTEIN TARGET 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
39106476 10.1021/acs.jmedchem.4c00982 NCI-H446 10
25835359 10.1016/j.bmc.2015.03.031 Mus musculus 8
15920768 10.1002/jps.20373 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18790776 10.1158/1535-7163.mct-08-0492 SW-620 8
37438997 10.1021/acs.jmedchem.3c00082 HCT-116 7

Data from ChEMBL 36 via Core Engine