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Details

Stereochemistry ACHIRAL
Molecular Formula C21H18FN5O5S
Molecular Weight 471.462
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Avutometinib

SMILES

CNS(=O)(=O)NC1=NC=CC(CC2=C(C)C3=CC=C(OC4=NC=CC=N4)C=C3OC2=O)=C1F

InChI

InChIKey=LMMJFBMMJUMSJS-UHFFFAOYSA-N
InChI=1S/C21H18FN5O5S/c1-12-15-5-4-14(31-21-25-7-3-8-26-21)11-17(15)32-20(28)16(12)10-13-6-9-24-19(18(13)22)27-33(29,30)23-2/h3-9,11,23H,10H2,1-2H3,(H,24,27)

HIDE SMILES / InChI

Molecular Formula C21H18FN5O5S
Molecular Weight 471.462
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Targets
PubMed

PubMed

TitleDatePubMed
MEK and the inhibitors: from bench to bedside.
2013 Apr 12
Patents
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:55:54 UTC 2023
Edited
by admin
on Wed Jul 05 23:55:54 UTC 2023
Record UNII
D0D4252V97
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Avutometinib
USAN   INN  
Official Name English
R-7304
Code English
N-[3-fluoro-4-({4-methyl-2-oxo-7-[(pyrimidin-2-yl)oxy]-2H-1-benzopyran-3-yl}methyl)pyridin-2-yl]-N′-methylsulfuric diamide
Systematic Name English
CKI-27
Code English
Avutometinib [WHO-DD]
Common Name English
avutometinib [INN]
Common Name English
VS-6766
Code English
Sulfamide, N-[3-fluoro-4-[[4-methyl-2-oxo-7-(2-pyrimidinyloxy)-2H-1-benzopyran-3-yl]methyl]-2-pyridinyl]-N′-methyl-
Systematic Name English
RO-5126766
Code English
RG-7304
Code English
CH-5126766
Code English
CH5126766
Code English
AVUTOMETINIB [USAN]
Common Name English
RO-5126766 FREE BASE
Code English
Code System Code Type Description
DRUG BANK
DB15254
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
USAN
LM-17
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
PUBCHEM
16719221
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL3545081
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
FDA UNII
D0D4252V97
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
CAS
946128-88-7
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
NCI_THESAURUS
C80060
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
RO-5126766 FREE BASE
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY In vitro: In HCT116 KRAS-mutant colorectal cancer cells, CH5126766 significantly reduces the levels of phospho-MEK and phospho-ERK. CH5126766 inhibits RAF kinase by binding to MEK1, and causes MEK to become a dominant negative inhibitor of RAF. In Raf or RAS-mutant cell lines SK-MEL-28, SK-MEL-2, MIAPaCa-2, SW480, HCT116, and PC3 cells, CH5126766 inhibits cell growth with IC50 of 65, 28, 40, 46, and 277 nM, respectively. In two melanoma cell lines with the BRAF V600E or NRAS mutation, RO5126766 induces G1 cell cycle arrest accompanied by up-regulation of the CDK inhibitor p27 and down-regulation of cyclinD1. In vivo: In an HCT116 (G13D KRAS) mouse xenograft model, CH5126766 (25 mg/kg, p.o.) inhibits ERK signaling output more effectively than a standard MEK inhibitor that induces MEK phosphorylation and has potent antitumor activity. In the HCT116 (K-ras) and COLO205 (B-raf) mutant xenografts, CH5126766 (0.3 mg/kg) causes significant decreases in (18F)FDG uptake. In the SK-MEL-2 xenograft model, RO5126766 also suppresses the tumor growth.
SMS_ID
300000027351
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
INN
11815
Created by admin on Wed Jul 05 23:55:54 UTC 2023 , Edited by admin on Wed Jul 05 23:55:54 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
Causes MEK to adopt a conformation in which it cannot be phosphorylated by and released from RAF.
IC50
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY
RO-5126766 RG-7304 CH-5126766 CKI-27 R-7304 CAS No. 946128-88-7