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Compound Detail

CHEMBL3218576

COPANLISIB
💊 Approved Drug
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💊 Approved Drug
COc1c(OCCCN2CCOCC2)ccc2c1N=C(NC(=O)c1cnc(N)nc1)N1CCN=C21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3218576
Name COPANLISIB
Phase Approved
Structure Type MOL
InChI Key PZBCKZWLPGJMAO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BAY 80-6946 Bay-80-6946 BAY80-6946 Copanlisib
14
Targets
41
Activities
2
Assay Types
0
PK Parameters
20
Publications
4
Known Names
20
Indications
2
Mechanisms

Molecular Properties

480.5
MW (Da)
0.66
ALogP
11
HBA
2
HBD
139.8
PSA (Ų)
0.55
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Discontinued
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product First in Class
USAN Stem -lisib
USAN Year 2015

Extended Properties

Molecular Formula C23H28N8O4
MW 480.53
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness -1.06

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
PI3-kinase p110-alpha subunit inhibitor INHIBITOR Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform ✓ ✓
PI3-kinase p110-delta subunit inhibitor INHIBITOR Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform ✓ ✓

Indications

Neoplasms Lymphoma, Non-Hodgkin Breast Neoplasms Breast Neoplasms Cholangiocarcinoma Endometrial Neoplasms Gallbladder Neoplasms Leukemia, Lymphocytic, Chronic, B-Cell Lymphoma, B-Cell, Marginal Zone Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Lymphoma, Mantle-Cell Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Colonic Neoplasms Lymphoma Prostatic Neoplasms, Castration-Resistant Renal Insufficiency Urinary Bladder Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma

ATC Classification

L01EM02
copanlisib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 40 meas. best 9.96
Kd 1 meas. best 5.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PI3-kinase p110-alpha/p85-alpha
CHEMBL2111367
 IC50 9.96 9.96 0.1 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 9.96 9.335 0.1 6
PI3-kinase p110-delta/p85-alpha
CHEMBL2111432
 IC50 9.74 9.74 0.2 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 IC50 9.74 8.5633 0.2 6
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 IC50 9.15 8.5757 0.7 7
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
CHEMBL3145
 IC50 8.43 8.35 3.7 6
PI3K p110 beta/p85 alpha
CHEMBL3038510
 IC50 8.34 8.34 4.6 1
MCF7
CHEMBL387
 IC50 8.0 8.0 10.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 7.35 7.35 45.0 3
LoVo
CHEMBL614721
 IC50 7.28 7.25 53.0 2
HCT-116
CHEMBL394
 IC50 6.92 6.905 120.0 2
HT-29
CHEMBL384
 IC50 6.03 6.025 930.0 2
Ras-related protein Rab-27A
CHEMBL4105702
 Kd 5.35 5.35 4493.0 1
HUVEC
CHEMBL613979
 IC50 4.46 4.455 34750.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 0.11 nM 9.96 Inhibition of PI3Kalpha (unknown origin) using PIP2 as substrate incubated for 1... 36586298
PI3-kinase p110-alpha/p85-alpha IC50 = 0.11 nM 9.96 Inhibition of recombinant human full-length N-terminal His-tagged p110alpha/p85a... 32069401
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 0.18 nM 9.74 Inhibition of PI3Kdelta (unknown origin) using PIP2 as substrate incubated for 1... 36586298
PI3-kinase p110-delta/p85-alpha IC50 = 0.18 nM 9.74 Inhibition of human full-length His-tagged p110delta/p85alpha expressed in bacul... 32069401
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 0.5 nM 9.3 Inhibition of PI3Kalpha (unknown origin) using PI:PS as substrate after 2 hrs in... 27479483
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 0.5 nM 9.3 Inhibition of PI3Kalpha (unknown origin) 31581005
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 0.5 nM 9.3 Inhibition of PI3Kalpha (unknown origin) 30582807
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 0.5 nM 9.3 Inhibition of P13Kalpha (unknown origin) 36462440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 0.7 nM 9.15 Inhibition of PI3Kdelta (unknown origin) using PI:PS as substrate after 2 hrs in... 27479483
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 0.7 nM 9.15 Inhibition of PI3Kgamma (unknown origin) 31581005
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 0.7 nM 9.15 Inhibition of P13Kgamma (unknown origin) 36462440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 1.42 nM 8.85 Inhibition of PI3Kalpha (unknown origin) using PIP2 as substrate preincubated fo... 38183777
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 1.68 nM 8.78 Inhibition of recombinant human full-length His-tagged p110gamma expressed in ba... 32069401
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 1.68 nM 8.78 Inhibition of PI3Kgamma (unknown origin) using PIP2 as substrate incubated for 1... 36586298
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 1.72 nM 8.76 Inhibition of PI3Kdelta (unknown origin) using PIP2 as substrate preincubated fo... 38183777
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 3.7 nM 8.43 Inhibition of PI3Kbeta (unknown origin) using PI:PS as substrate after 2 hrs in ... 27479483
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 3.7 nM 8.43 Inhibition of PI3Kbeta (unknown origin) 31581005
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 3.7 nM 8.43 Inhibition of PI3Kbeta (unknown origin) 30582807
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 3.7 nM 8.43 Inhibition of P13Kbeta (unknown origin) 36462440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 4.57 nM 8.34 Inhibition of PI3Kbeta (unknown origin) using PIP2 as substrate incubated for 1 ... 36586298

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5303300 U2OS 304
- 10.6019/CHEMBL5303300 HEK-293T 304
- 10.6019/CHEMBL5303300 Fibroblast 304
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5303304 HEK-293T 9
- 10.6019/CHEMBL5303304 Fibroblast 8
36586298 10.1016/j.ejmech.2022.115030 ADMET 7
- 10.6019/CHEMBL5303304 U2OS 6
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
29191878 10.1126/science.aan4368 Unchecked 5
32069401 10.1021/acs.jmedchem.9b01736 HCT-116 4
36586298 10.1016/j.ejmech.2022.115030 HT-29 2
32069401 10.1021/acs.jmedchem.9b01736 HT-29 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine