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Details

Stereochemistry RACEMIC
Molecular Formula C19H23F2N5O2
Molecular Weight 391.415
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-[(3,5-Difluoro-4-hydroxyphenyl)amino]-7,8-dihydro-5,7-dimethyl-8-(3-methylbutyl)-6(5H)-pteridinone

SMILES

CC(C)CCN1C(C)C(=O)N(C)C2=C1N=C(NC3=CC(F)=C(O)C(F)=C3)N=C2

InChI

InChIKey=DTEKTGDVSARYDS-UHFFFAOYSA-N
InChI=1S/C19H23F2N5O2/c1-10(2)5-6-26-11(3)18(28)25(4)15-9-22-19(24-17(15)26)23-12-7-13(20)16(27)14(21)8-12/h7-11,27H,5-6H2,1-4H3,(H,22,23,24)

HIDE SMILES / InChI

Molecular Formula C19H23F2N5O2
Molecular Weight 391.415
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24241211 | https://www.ncbi.nlm.nih.gov/pubmed/26386981

BI-D1870 is a small molecule, which inhibits RSK1, RSK2, RSK3 and RSK4 in vitro with an IC(50) of 10-30 nM, but does not significantly inhibit ten other AGC kinase members and over 40 other protein kinases tested at 100-fold higher concentrations. BI-D1870 is cell permeant and prevents the RSK-mediated phorbol ester- and EGF (epidermal growth factor)-induced phosphorylation of glycogen synthase kinase-3beta and LKB1 in human embryonic kidney 293 cells and Rat-2 cells. BI-D1870 exhibited a dose-responsive antiproliferative effect on OSCC cells with relative sparing of normal human oral keratinocytes. The compound inhibited the downstream RSK target YB-1 and caused apoptosis. In addition, BI-D1870 also induced G2/M arrest by modulating the expression of p21 and other cell cycle regulators. BI-D1870 may be of useful in oral squamous cell carcinoma therapy. BI-D1870 has being shown to ameliorate experimental autoimmune encephalomyelitis in mice. BI-D1870 administration protected mice from EAE by reducing the infiltration of TH1 and TH17 cells into the CNS and decreasing mRNA levels of Ccr6 in TH17 cells. These results suggest that RSK inhibition is a promising strategy for the treatment of MS.

CNS Activity

Curator's Comment: BI-D1870 administration protected mice from EAE by reducing the infiltration of TH1 and TH17 cells into the CNS and decreasing mRNA levels of Ccr6 in TH17 cells. These results suggest that RSK inhibition is a promising strategy for the treatment of MS. n mice, BI-D1870 was well-tolerated and crossed the blood-brain barrier (BBB) https://www.ncbi.nlm.nih.gov/pubmed/23940083

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
BI-D1870 is a specific inhibitor of the p90 RSK (ribosomal S6 kinase) isoforms in vitro and in vivo.
2007 Jan 1
Antitumor effects of BI-D1870 on human oral squamous cell carcinoma.
2014 Feb
Overcoming resistance to Sonic Hedgehog inhibition by targeting p90 ribosomal S6 kinase in pediatric medulloblastoma.
2014 Jan
Patents

Sample Use Guides

Mice: BI-D1870 (0.5 mg/kg) was injected i.p. into mice two days after immunization with MOG peptide, and injection was repeated every other day for 11 days
Route of Administration: Intraperitoneal
At 0.1 uM BI-D1870 inhibited the four RSK isoforms by over 98%
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:09:28 GMT 2023
Edited
by admin
on Sat Dec 16 09:09:28 GMT 2023
Record UNII
WLN44M8WHJ
Record Status Validated (UNII)
Record Version
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Name Type Language
2-[(3,5-Difluoro-4-hydroxyphenyl)amino]-7,8-dihydro-5,7-dimethyl-8-(3-methylbutyl)-6(5H)-pteridinone
Systematic Name English
6(5H)-Pteridinone, 2-[(3,5-difluoro-4-hydroxyphenyl)amino]-7,8-dihydro-5,7-dimethyl-8-(3-methylbutyl)-
Systematic Name English
BI-D1870
Code English
BI-D 1870
Code English
Code System Code Type Description
PUBCHEM
25023738
Created by admin on Sat Dec 16 09:09:28 GMT 2023 , Edited by admin on Sat Dec 16 09:09:28 GMT 2023
PRIMARY
FDA UNII
WLN44M8WHJ
Created by admin on Sat Dec 16 09:09:28 GMT 2023 , Edited by admin on Sat Dec 16 09:09:28 GMT 2023
PRIMARY
CAS
501437-28-1
Created by admin on Sat Dec 16 09:09:28 GMT 2023 , Edited by admin on Sat Dec 16 09:09:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID40648506
Created by admin on Sat Dec 16 09:09:28 GMT 2023 , Edited by admin on Sat Dec 16 09:09:28 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR