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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H22N6O3
Molecular Weight 454.4806
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Tirabrutinib

SMILES

CC#CC(=O)N1CC[C@H](C1)N2C(=O)N(C3=C(N)N=CN=C23)C4=CC=C(OC5=CC=CC=C5)C=C4

InChI

InChIKey=SEJLPXCPMNSRAM-GOSISDBHSA-N
InChI=1S/C25H22N6O3/c1-2-6-21(32)29-14-13-18(15-29)31-24-22(23(26)27-16-28-24)30(25(31)33)17-9-11-20(12-10-17)34-19-7-4-3-5-8-19/h3-5,7-12,16,18H,13-15H2,1H3,(H2,26,27,28)/t18-/m1/s1

HIDE SMILES / InChI
Molecular Formula C25H22N6O3
Molecular Weight 454.4806
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Tirabrutinib (also known as ONO-4059 or GS-4059), a second-generation, enhanced-selectivity Bruton's tyrosine kinase inhibitor that demonstrated antitumor activity in preclinical models. Tirabrutinib participated in phase I clinical trial in patients with relapsed or refractory B-cell malignancies, where it was well tolerated and showed promising efficacy. In addition, tirabrutinib is involved in phase II clinical trials to study safety and efficacy in adults with Active Sjogren's syndrome and in adults with chronic lymphocytic leukemia. Besides the drug was studied for the treatment of Waldenstrom's macroglobulinemia and patients with refractory pemphigus.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 11.0 nM [IC50]
Inhibitor
8297
 2.2 nM [IC50]
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

In Vivo Use Guide
40 mg tablet administered orally once daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:41:23 UTC 2023
Edited
by admin
on Sat Dec 16 09:41:23 UTC 2023
Record UNII
LXG44NDL2T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Tirabrutinib
INN   WHO-DD  
USAN   INN  
Official Name English
6-amino-9-[(3R)-1-(but-2-ynoyl)pyrrolidin-3-yl]-7-(4-phenoxyphenyl)-7,9-dihydro-8H-purin-8-one
Systematic Name English
GS-4059
Code English
TIRABRUTINIB [USAN]
Common Name English
8H-Purin-8-one, 6-amino-7,9-dihydro-9-[(3R)-1-(1-oxo-2-butyn-1-yl)-3-pyrrolidinyl]-7-(4-phenoxyphenyl)-
Systematic Name English
tirabrutinib [INN]
Common Name English
ONO-4059(FREE BASE)
Code English
Tirabrutinib [WHO-DD]
Common Name English
ONO-4059
Code English
Classification Tree Code System Code
NCI_THESAURUS C124801
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
FDA ORPHAN DRUG 930322
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
Code System Code Type Description
FDA UNII
LXG44NDL2T
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
SMS_ID
100000172855
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
NCI_THESAURUS
C102876
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
WIKIPEDIA
Tirabrutinib
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
INN
10320
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
TIRABRUTINIB
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY MedKoo CAT NO.: 205914, CAS NO.: 1351635-67-0Description: ONO4059-Analog, CAS#1351635-67-0, is a potent and selective BTK inhibitor, and is a structural analogue of ONO-4059. ONO4059 is currently under clinical trials. Note: ONO4059 HCl has CAS#1439901-97-9, ONO4059 free base has CAS#1351636-18-4. (Last updated: 5/19/2016).Synonym: ONO4059-Analog, ONO 4059-Analog, ONO-4059-Analog, GS 4059-Analog, GS-4059-Analog, GS4059-Analog.IUPAC/Chemical Name: (S)-9-(1-acryloylpiperidin-3-yl)-6-amino-7-(4-phenoxyphenyl)-7,9-dihydro-8H-purin-8-one
CAS
1351636-18-4
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
PUBCHEM
54755438
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
USAN
LM-62
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
DRUG BANK
DB15227
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL3544928
Created by admin on Sat Dec 16 09:41:24 UTC 2023 , Edited by admin on Sat Dec 16 09:41:24 UTC 2023
PRIMARY
Related Record Type Details
Structure of Tirabrutinib Hydrochloride
SALT/SOLVATE -> PARENT
TYROSINE-PROTEIN KINASE BTK
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
IC50
Related Record Type Details
Structure of Tirabrutinib
ACTIVE MOIETY
Drugs: GS 4059(Primary), Entospletinib, Idelalisib; Indication: B cell lymphoma; Focus: Adverse reactions, Therapeutic Use; Sponsor: Gilead Sciences; Most Recent Events: 26 Jun 2016 Planned number of patients changed from 320 to 338., 10 May 2016 Planned End Date changed from 1 Jun 2018 to 1 Jan 2019., 10 May 2016 Planned primary completion date changed from 1 Jun 2017 to 1 Dec 2018.
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