U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C27H28F3N7O3
Molecular Weight 555.5515
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROCILETINIB

SMILES

COC1=CC(=CC=C1NC2=NC=C(C(NC3=CC(NC(=O)C=C)=CC=C3)=N2)C(F)(F)F)N4CCN(CC4)C(C)=O

InChI

InChIKey=HUFOZJXAKZVRNJ-UHFFFAOYSA-N
InChI=1S/C27H28F3N7O3/c1-4-24(39)32-18-6-5-7-19(14-18)33-25-21(27(28,29)30)16-31-26(35-25)34-22-9-8-20(15-23(22)40-3)37-12-10-36(11-13-37)17(2)38/h4-9,14-16H,1,10-13H2,2-3H3,(H,32,39)(H2,31,33,34,35)

HIDE SMILES / InChI

Molecular Formula C27H28F3N7O3
Molecular Weight 555.5515
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/history/rociletinib.html http://www.ema.europa.eu/docs/en_GB/document_library/Medicine_QA/2016/05/WC500207169.pdf

Rociletinib is a novel, potent, small molecule, third generation TKI that irreversibly binds and inhibits EGFR with the common activating (L858R, Del19) and T790M resistance mutations. The proposed indication of rociletinib is for the treatment of patients with mutant EGFR NSCLC who have been previously treated with an EGFR-targeted therapy and have the T790M mutation as detected by an FDA approved test. The results from two Phase 2 studies show that rociletinib 625 mg BID treatment has a favorable benefit:risk profile in patients with recurrent T790M-positive mutant EGFR NSCLC based on clinically meaningful and durable responses and a well-established and acceptable safety profile in this patient population with terminal lung cancer. In May 2016, Clovis Oncology, Inc. announced it has terminated enrollment in all ongoing sponsored studies of rociletinib, including TIGER-3, after the company was notified at meeting with the FDA that it could anticipate receiving a Complete Response Letter (CRL) for the rociletinib NDA on or before the PDUFA date of June 28, 2016. Clovis has also withdrawn its Marketing Authorization Application of rociletinib with European regulatory authorities.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
21.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Discovery of a mutant-selective covalent inhibitor of EGFR that overcomes T790M-mediated resistance in NSCLC.
2013 Dec
Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in lung cancers.
2013 Feb 1
Patents

Sample Use Guides

Clovis’ proposed recommended dose was 500 mg BID.
Route of Administration: Oral
Rociletinib inhibits p-EGFR with IC50 ranging from 62 to 187 nM in the mutant NSCLC EGFR–expressing cells
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:35:50 GMT 2023
Edited
by admin
on Sat Dec 16 01:35:50 GMT 2023
Record UNII
72AH61702G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROCILETINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
2-PROPENAMIDE, N-(3-((2-((4-(4-ACETYL-1-PIPERAZINYL)-2-METHOXYPHENYL)AMINO)-5-(TRIFLUOROMETHYL)-4-PYRIMIDINYL)AMINO)PHENYL)-
Systematic Name English
CNX-419
Code English
rociletinib [INN]
Common Name English
CO-1686
Code English
N-(3-{[2-{[4-(4-Acetylpiperazin-1-yl)-2-methoxyphenyl]amino}-5-(trifluoromethyl)pyrimidin-4-yl]amino}phenyl)prop-2-enamide
Systematic Name English
ROCILETINIB [USAN]
Common Name English
Rociletinib [WHO-DD]
Common Name English
CS-1631
Code English
AVL-301
Code English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
FDA ORPHAN DRUG 380212
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
NCI_THESAURUS C2167
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
WHO-ATC L01XE37
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
Code System Code Type Description
FDA UNII
72AH61702G
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
SMS_ID
100000162726
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
CAS
1374640-70-6
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
PUBCHEM
57335384
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
USAN
BC-151
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
NCI_THESAURUS
C99905
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
WIKIPEDIA
Rociletinib
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID801025958
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
EVMPD
SUB176681
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
INN
9986
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL3545308
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
DRUG BANK
DB11907
Created by admin on Sat Dec 16 01:35:50 GMT 2023 , Edited by admin on Sat Dec 16 01:35:50 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY