Olmutinib

CovInDB Drug

DB13164

Name

Olmutinib

Molecular Formula

C₂₆H₂₆N₆O₂S

Molecular Weight

486.18 g/mol

Description

Olmutinib is an orally active epidermal growth factor receptor inhibitor used in the treatment of T790M mutation positive non-small cell lung cancer. It is available under the brand name Olita made by Hanmi Pharmaceuticals . Olmutinib was developed by Hanmi Pharmaceuticals and Boehringer Ingelheim. Olmutinib recieved breakthrough therapy designation in the United States in December 2015 and was approved for use in Korea in May 2016.

Status

investigational

Structure

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SDF 2D SDF 3D

Indication

For use in treatment of metastatic T790M mutation positive non-small cell lung cancer .

Mechanism of action

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Olmutinib covalently binds a cysteine residue near the kinase domain of mutant EGFRs to prevent phosphorylation of the receptor . This inhibits receptor signalling as phosphorylation is necessary for recruitment of signalling cascade proteins.

IUPAC Name

N-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide

InChI

InChI=1S/C26H26N6O2S/c1-3-23(33)27-19-5-4-6-21(17-19)34-25-24-22(11-16-35-24)29-26(30-25)28-18-7-9-20(10-8-18)32-14-12-31(2)13-15-32/h3-11,16-17H,1,12-15H2,2H3,(H,27,33)(H,28,29,30)

InChI Key

FDMQDKQUTRLUBU-UHFFFAOYSA-N

Canonical SMILES

CN1CCN(CC1)C1=CC=C(NC2=NC(OC3=CC=CC(NC(=O)C=C)=C3)=C3SC=CC3=N2)C=C1

Reference

DrugBank

Warhead

Micheal Acceptor

Target

Epidermal growth factor receptor   [ UniProt: P00533 ]

Site

CYS-797

Inhibition Mechanism

logP

5.22

Computed by ALOGPS

logS

-4.79

Computed by ALOGPS

Heavy Atom Count

35

Computed by RDKit

Ring Count

5

Computed by RDKit

Hydrogen Bond Acceptor Count

8

Computed by RDKit

Hydrogen Bond Donor Count

2

Computed by RDKit

Rotatable Bond Count

7

Computed by RDKit

Topological Polar Surface Area

82.62 Ų

Computed by RDKit

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No similar natural compounds found for this drug.