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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H24F3N5O3
Molecular Weight 571.5503
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UMBRALISIB

SMILES

CC(C)Oc1ccc(cc1F)-c2c3c(N)ncnc3n([C@@]([H])(C)c4c(-c5cccc(c5)F)c(=O)c6cc(ccc6o4)F)n2

InChI

InChIKey=IUVCFHHAEHNCFT-INIZCTEOSA-N
InChI=1S/C31H24F3N5O3/c1-15(2)41-24-9-7-18(12-22(24)34)27-26-30(35)36-14-37-31(26)39(38-27)16(3)29-25(17-5-4-6-19(32)11-17)28(40)21-13-20(33)8-10-23(21)42-29/h4-16H,1-3H3,(H2,35,36,37)/t16-/m0/s1

HIDE SMILES / InChI
Umbralisib (TGR-1202) is an orally available PI3K delta inhibitor, targeting the delta isoform with nanomolar potency and several fold selectivity over the alpha, beta, and gamma isoforms of PI3K. The delta isoform of PI3K is strongly expressed in cells of hematopoietic origin and is believed to be important in the proliferation and survival of B-cell lymphocytes. Inhibition of PI3K delta signaling with umbralisib has demonstrated robust activity in numerous pre-clinical models and primary cells from patients with hematologic malignancies. Umbralisib is currently in Phase 3 clinical development in combination with Ublituximab for patients with hematologic malignancies.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
22.1999999999999993 nM [EC50]
Target ID: P49674
Gene ID: 102800317|||1454
Gene Symbol: CSNK1E
Target Organism: Homo sapiens (Human)
Target ID: O00329
Gene ID: 5293
Gene Symbol: PIK3CD
Target Organism: Homo sapiens (Human)
6.20000000000000018 nM [Kd]
Target ID: P49674
Gene ID: 102800317|||1454
Gene Symbol: CSNK1E
Target Organism: Homo sapiens (Human)
180 nM [Kd]
PubMed

PubMed

TitleDatePubMed
Can umbralisib bring PI3Kδ out of the shadows?
2018 Apr
Umbralisib: Treatment for a Rare Lymphoma?
2019 Jun
Patents

Patents

Sample Use Guides

relapsed or refractory chronic lymphocytic leukaemia or mantle cell lymphoma: umbralisib orally once daily (400 mg, 600 mg, or 800 mg) and ibrutinib orally once daily (420 mg for chronic lymphocytic leukaemia or 560 mg for mantle cell lymphoma) until disease progression or unacceptable toxicity. Umbralisib plus ibrutinib is well tolerated and active in relapsed or refractory chronic lymphocytic leukaemia and mantle cell lymphoma, with a recommended phase 2 dose of umbralisib 800 mg once daily.
Route of Administration: Oral
Umbralisib (TGR-1202), a novel, next generation PI3Kδ inhibitor, inhibits PI3Kδ activity in enzyme and cell based assays with IC50 and EC50 values of 22.2 & 24.3 nM, respectively.
Name Type Language
UMBRALISIB
USAN   INN  
Official Name English
RP-5264
Code English
4H-1-BENZOPYRAN-4-ONE, 2-((1S)-1-(4-AMINO-3-(3-FLUORO-4-(1-METHYLETHOXY)PHENYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-1-YL)ETHYL)-6-FLUORO-3-(3-FLUOROPHENYL)-
Systematic Name English
UMBRALISIB [WHO-DD]
Common Name English
2-((1S)-1-(4-AMINO-3-(3-FLUORO-4-(1-METHYLETHOXY)PHENYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-1-YL)ETHYL)-6-FLUORO-3-(3-FLUOROPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
TGR-1202
Code English
UMBRALISIB [USAN]
Common Name English
UMBRALISIB [INN]
Common Name English
RP5264
Code English
TGR-1202 FREE BASE
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 533016
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
NCI_THESAURUS C129825
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
FDA ORPHAN DRUG 687419
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
FDA ORPHAN DRUG 680019
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
FDA ORPHAN DRUG 687519
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
FDA ORPHAN DRUG 554216
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
NCI_THESAURUS C2152
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
FDA ORPHAN DRUG 726819
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
FDA ORPHAN DRUG 552216
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
Code System Code Type Description
DRUG BANK
DB14989
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY
NCI_THESAURUS
C104413
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY
CAS
1532533-67-7
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY
PUBCHEM
72950888
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY
MANUFACTURER PRODUCT INFORMATION
TGR-1202 FREE BASE
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY MedKoo CAT NO: 205938, CAS NO.: 1532533-67-7(free base), 1532533-75-7(sulfate)Description: TGR-1202, also known as RP5264 , is a highly specific, orally available, PI3K delta inhibitor, targeting the delta isoform with nanomolar potency and several fold selectivity over the alpha, beta, and gamma isoforms of PI3K. Inhibition of PI3K delta signaling with TGR-1202 has demonstrated robust activity in numerous pre-clinical models and primary cells from patients with hematologic malignancies.(Last Updated: 9/24/2015)
FDA UNII
38073MQB2A
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY
INN
10350
Created by admin on Sat Jun 26 10:50:06 UTC 2021 , Edited by admin on Sat Jun 26 10:50:06 UTC 2021
PRIMARY