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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H24F3N5O3.C7H8O3S
Molecular Weight 743.7533
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UMBRALISIB TOSYLATE

SMILES

CC(C)Oc1ccc(cc1F)-c2c3c(N)ncnc3n([C@@]([H])(C)c4c(-c5cccc(c5)F)c(=O)c6cc(ccc6o4)F)n2.Cc1ccc(cc1)S(=O)(=O)O

InChI

InChIKey=KYJWUPZPSXZEPG-NTISSMGPSA-N
InChI=1S/C31H24F3N5O3.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h4-16H,1-3H3,(H2,35,36,37);2-5H,1H3,(H,8,9,10)/t16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C7H8O3S
Molecular Weight 172.203
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C31H24F3N5O3
Molecular Weight 571.5503
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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 Inhibits PI3Kδ with Less Toxicity Than Previous Inhibitors.
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:13:18 UTC 2021
Edited
by admin
on Sat Jun 26 09:13:18 UTC 2021
Record UNII
FU8XW5V3FS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UMBRALISIB TOSYLATE
Common Name English
UKONIQ
Brand Name English
UMBRALISIB TOSYLATE [USAN]
Common Name English
TGR-1202 (4-METHYLBENZENESULFONATE)
Code English
RP-5307
Code English
2-((1S)-1-(4-AMINO-3-(3-FLUORO-4-(PROPAN-2-YLOXY)PHENYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-1-YL)ETHYL)-6-FLUORO-3-(3-FLUOROPHENYL)-4H-1-BENZOPYRAN-4-ONE MONO(4-METHYLBENZENESULFONATE)
Systematic Name 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)-,4-METHYLBENZENESULFONATE
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
NCI_THESAURUS C2152
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
Code System Code Type Description
CAS
1532533-72-4
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
PRIMARY
ChEMBL
CHEMBL3545267
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
PRIMARY
PUBCHEM
86707828
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
PRIMARY
FDA UNII
FU8XW5V3FS
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
PRIMARY
NCI_THESAURUS
C152795
Created by admin on Sat Jun 26 09:13:18 UTC 2021 , Edited by admin on Sat Jun 26 09:13:18 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY