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Umbralisib (tosylate)

CAT: 0804-HY-12279ASize: 1 EachDry Ice: NoHazardous: No
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Description
Umbralisib (TGR-1202) tosylate is an orally active, potent and selective dual PI3Kδ and casein kinase-1-ε (CK1ε) inhibitor, with EC50 of 22.2 nM and 6.0 μM, respectively. Umbralisib tosylate exhibits unique immunomodulatory effects on chronic lymphocytic leukemia (CLL) T cells. Umbralisib tosylate can be used for haematological malignancies reseach[1][2][3][4].
CAS Number
1532533-72-4
Product Name Alternative
TGR-1202 (tosylate) ; RP5264 (tosylate)
UNSPSC
12352005
Target
Casein Kinase; PI3K
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage; PI3K/Akt/mTOR; Stem Cell/Wnt
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/umbralisib-tosylate.html
Solubility
10 mM in DMSO
Smiles
O=C1C(C2=CC=CC(F)=C2)=C([C@@H](N3N=C(C4=CC=C(OC(C)C)C(F)=C4)C5=C(N)N=CN=C53)C)OC6=CC=C(F)C=C16.O=S(C7=CC=C(C)C=C7)(O)=O
Molecular Formula
C38H32F3N5O6S
Molecular Weight
743.75
References & Citations
[1]Maharaj K, et al. The dual PI3Kδ/CK1ε inhibitor umbralisib exhibits unique immunomodulatory effects on CLL T cells. Blood Adv. 2020 Jul 14;4 (13) :3072-3084.|[2]Burris HA 3rd, et al. Umbralisib, a novel PI3Kδ and casein kinase-1ε inhibitor, in relapsed or refractory chronic lymphocytic leukaemia and lymphoma: an open-label, phase 1, dose-escalation, first-in-human study. Lancet Oncol. 2018 Apr;19 (4) :486-496.|[3]Swaroop Vakkalankaa, et al. Inhibition of PI3Kδ kinase by a selective, small molecule inhibitor suppresses B-cell proliferation and leukemic cell growth.|[4]Deng C, et al. Silencing c-Myc translation as a therapeutic strategy through targeting PI3Kδ and CK1ε in hematological malignancies. Blood. 2017 Jan 5;129 (1) :88-99.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
CK1; PI3Kα; PI3Kβ; PI3Kγ; PI3Kδ

Chemical Information

Umbralisib Tosylate

Umbralisib Tosylate is the tosylate form of umbralisib, an orally bioavailable, selective inhibitor of the delta isoform of the 110 kDa catalytic subunit of class I phosphoinositide-3 kinases (PI3K) with potential antineoplastic activity. umbralisib inhibits PI3K and prevents the activation of the PI3K/AKT kinase signaling pathway. This decreases proliferation and induces cell death in susceptible tumor cells. Unlike other isoforms of PI3K, PI3K-delta is expressed primarily in tumor cells and cells of the hematopoietic lineage. The targeted inhibition of PI3K-delta allows for PI3K signaling in normal, non-neoplastic cells. PI3K, an enzyme often overexpressed in cancer cells, plays a crucial role in tumor cell regulation and survival.

CAS Number1532533-72-4
PubChem CID86707828
IUPAC Name2-[(1S)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one;4-methylbenzenesulfonic acid
Molecular FormulaC38H32F3N5O6S
Molecular Weight743.8
Topological Polar Surface Area168
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Heavy Atom Count53
Formal Charge0
Complexity1220
SMILES
CC1=CC=C(C=C1)S(=O)(=O)O.C[C@@H](C1=C(C(=O)C2=C(O1)C=CC(=C2)F)C3=CC(=CC=C3)F)N4C5=NC=NC(=C5C(=N4)C6=CC(=C(C=C6)OC(C)C)F)N
InChI
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
InChIKey
KYJWUPZPSXZEPG-NTISSMGPSA-N
Chemical Structure
2D Structure
2D structure of Umbralisib Tosylate
CAS: 1532533-72-4
CID: 86707828
Formula: C38H32F3N5O6S
MW: 743.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight743.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Exact Mass743.20253942
Monoisotopic Mass743.20253942
Topological Polar Surface Area168 Ų
Heavy Atom Count53
Formal Charge0
Complexity1220
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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