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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H27FN10
Molecular Weight 498.558
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AVAPRITINIB

SMILES

CN1C=C(C=N1)C2=CN3N=CN=C(N4CCN(CC4)C5=NC=C(C=N5)[C@@](C)(N)C6=CC=C(F)C=C6)C3=C2

InChI

InChIKey=DWYRIWUZIJHQKQ-SANMLTNESA-N
InChI=1S/C26H27FN10/c1-26(28,20-3-5-22(27)6-4-20)21-13-29-25(30-14-21)36-9-7-35(8-10-36)24-23-11-18(16-37(23)33-17-31-24)19-12-32-34(2)15-19/h3-6,11-17H,7-10,28H2,1-2H3/t26-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H27FN10
Molecular Weight 498.558
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Blu-285 is a potent and selective inhibitor for hematologic malignancies with KIT Exon 17 Mutations. BLU-285 has demonstrated biochemical in vitro activity on the KIT exon-17 mutant enzyme, KIT D816V. Cellular activity of BLU-285 on KIT D816 mutants was measured by autophosphorylation in the human mast cell leukemia cell line HMC1.2, and the P815 mouse mastocytoma cell line with IC50= 4 and 22 nM, respectively. In vivo BLU-285 was well tolerated and has demonstrated dose-dependent antitumor efficacy. Complete tumor growth inhibition and ≥ 75% KIT kinase inhibition was observed with 10 mg/kg once daily, oral dosing of BLU-285 in the aggressive KIT exon 17 mutant driven P815 mastocytoma model grown as a solid tumor allograft as well as in a disseminated model of the disease. BLU-285 was also well tolerated in this in vivo model and had no adverse effects on body weight at either dose.

Approval Year

PubMed

PubMed

TitleDatePubMed
BLU-285, DCC-2618 Show Activity against GIST.
2017 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
BLU-285 capsules or tablets for oral administration. BLU-285 will be dosed daily for 28 day cycles.
Route of Administration: Oral
In Vitro Use Guide
Cellular activity of BLU-285 on KIT D816 mutants was measured by autophosphorylation in the human mast cell leukemia cell line HMC1.2, and the P815 mouse mastocytoma cell line with IC50= 4 and 22 nM, respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:48:23 UTC 2019
Edited
by admin
on Mon Oct 21 20:48:23 UTC 2019
Record UNII
513P80B4YJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AVAPRITINIB
USAN   INN  
Official Name English
X-720776
Code English
70C366
Code English
C-366
Code English
(S)-1-(4-FLUOROPHENYL)-1-(2-(4-(6-(1-METHYL-1H-PYRAZOL-4-YL)PYRROLO(2,1-F)(1,2,4)TRIAZIN-4-YL)PIPERAZIN-YL)PYRIMIDIN-5-YL)ETHAN-1-AMINE
Systematic Name English
5-PYRIMIDINEMETHANAMINE, .ALPHA.-(4-FLUOROPHENYL)-.ALPHA.-METHYL-2-(4-(6-(1-METHYL-1H-PYRAZOL-4-YL)PYRROLO(2,1-F)(1,2,4)TRIAZIN-4-YL)-1-PIPERAZINYL)-, (.ALPHA.S)-
Systematic Name English
BLU-285
Code English
X720776
Code English
AVAPRITINIB [INN]
Common Name English
AVAPRITINIB [USAN]
Common Name English
AVAPRITINIB [WHO-DD]
Common Name English
(1S)-1-(4-FLUOROPHENYL)-1-(2-(4-(6-(1-METHYL-1H-PYRAZOL-4-YL)PYRROLO(2,1- F)(1,2,4)TRIAZIN-4-YL)PIPERAZIN-1-YL)PYRIMIDIN-5-YL)ETHAN-1-AMINE
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/18/2074
Created by admin on Mon Oct 21 20:48:23 UTC 2019 , Edited by admin on Mon Oct 21 20:48:23 UTC 2019
FDA ORPHAN DRUG 506515
Created by admin on Mon Oct 21 20:48:23 UTC 2019 , Edited by admin on Mon Oct 21 20:48:23 UTC 2019
FDA ORPHAN DRUG 500415
Created by admin on Mon Oct 21 20:48:23 UTC 2019 , Edited by admin on Mon Oct 21 20:48:23 UTC 2019
Code System Code Type Description
CAS
1703793-34-3
Created by admin on Mon Oct 21 20:48:23 UTC 2019 , Edited by admin on Mon Oct 21 20:48:23 UTC 2019
PRIMARY
PUBCHEM
118023034
Created by admin on Mon Oct 21 20:48:23 UTC 2019 , Edited by admin on Mon Oct 21 20:48:23 UTC 2019
PRIMARY
INN
10613
Created by admin on Mon Oct 21 20:48:23 UTC 2019 , Edited by admin on Mon Oct 21 20:48:23 UTC 2019
PRIMARY
Related Record Type Details
OFF-TARGET->INHIBITOR
>100— the free mean maximum plasma concentration at steady state [Cmax,ss] of 0.022 µM at the MTD in humans of 400 mg QD
IC50
METABOLIC ENZYME -> SUBSTRATE
MINOR
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
ACTIVE MOIETY