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Compound Detail

CHEMBL3948730

UMBRALISIB
💊 Approved Drug
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💊 Approved Drug
CC(C)Oc1ccc(-c2nn([C@@H](C)c3oc4ccc(F)cc4c(=O)c3-c3cccc(F)c3)c3ncnc(N)c23)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3948730
Name UMBRALISIB
Phase Approved
Structure Type MOL
InChI Key IUVCFHHAEHNCFT-INIZCTEOSA-N
Therapeutic ✓ Yes

Known Names

RP-5264 RP5264 Tgr 1202 TGR-1202 base TGR-1202 FREE BASE Umbralisib
5
Targets
11
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names
9
Indications

Molecular Properties

571.6
MW (Da)
6.66
ALogP
8
HBA
1
HBD
109.1
PSA (Ų)
0.24
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2021
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn
USAN Stem -lisib
USAN Year 2017

Extended Properties

Molecular Formula C31H24F3N5O3
MW 571.56
Aromatic Rings 6
Heavy Atoms 42
NP-Likeness -0.88

Indications

Neoplasms Hodgkin Disease Leukemia, Lymphocytic, Chronic, B-Cell Lymphoma, Follicular Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Lymphoma, Mantle-Cell Lymphoma, Non-Hodgkin Waldenstrom Macroglobulinemia

ATC Classification

L01EX25
umbralisib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Withdrawn
General Warning
possible increased risk of death
Country: United States   Year: 2022

Activity Summary

IC50 8 meas. best 8.21
EC50 2 meas. best 7.65
Kd 1 meas. best 8.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 IC50 8.21 7.5771 6.2 7
Unchecked
CHEMBL612545
 Kd 8.21 8.21 6.2 1
PI3-kinase p110-delta/p85-alpha
CHEMBL2111432
 EC50 7.65 7.65 22.2 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 IC50 5.85 5.85 1400.0 1
Casein kinase I isoform epsilon
CHEMBL4937
 EC50 5.22 5.22 6000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 6.2 nM 8.21 Inhibition of PI3Kdelta (unknown origin) 30530193
Unchecked Kd = 6.2 nM 8.21 Inhibition of PI3K (unknown origin) 34042449
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 14.0 nM 7.85 Inhibition of PI3Kdelta (unknown origin) using PIP2 as substrate preincubated fo... 30582813
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 14.0 nM 7.85 Affinity Biochemical interaction (Enzymatic inhibition assay) EUB0000696a PIK3CD -
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 22.0 nM 7.66 Inhibition of P13Kdelta (unknown origin) 36462440
PI3-kinase p110-delta/p85-alpha EC50 = 22.2 nM 7.65 Inhibition of recombinant human full-length N-terminal His6-tagged p110delta/rec... 27784673
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 22.33 nM 7.65 Homogenous Time Resolved Fluorescence (HTRF) Assay: The homogenous time resolved... -
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 48.4 nM 7.32 Inhibition of human PI3Kdelta using substrate PIP2:PS and ATP incubated for 1 hr... 33180507
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 316.0 nM 6.5 Inhibition of PI3Kdelta (unknown origin) using PIP2:PS as substrate in presence ... 37606563
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 1400.0 nM 5.85 Inhibition of PI3Kgamma (unknown origin) 30530193
Casein kinase I isoform epsilon EC50 = 6000.0 nM 5.22 Inhibition of recombinant human full-length N-terminal GST-tagged CK1epsilon exp... 27784673

Literature References

PubMed DOI Target Context # Activities
27784673 10.1182/blood-2016-08-731240 mTORC1 33
27784673 10.1182/blood-2016-08-731240 Unchecked 27
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
27784673 10.1182/blood-2016-08-731240 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform 10
- 10.6019/CHEMBL4689842 U2OS 10
- 10.6019/CHEMBL4689842 HEK-293T 10
27784673 10.1182/blood-2016-08-731240 Myc proto-oncogene protein 8
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
27784673 10.1182/blood-2016-08-731240 OCI-Ly10 5
27784673 10.1182/blood-2016-08-731240 OCI-Ly7 4
37606563 10.1021/acs.jmedchem.3c00508 Unchecked 3
27784673 10.1182/blood-2016-08-731240 H9 3
33180507 10.1021/acs.jmedchem.0c01544 Unchecked 3
27784673 10.1182/blood-2016-08-731240 Casein kinase I isoform epsilon 3
27784673 10.1182/blood-2016-08-731240 Z-138 3
27784673 10.1182/blood-2016-08-731240 PF-382 3
27784673 10.1182/blood-2016-08-731240 JeKo-1 3
27784673 10.1182/blood-2016-08-731240 HH 2

Data from ChEMBL 36 via Core Engine