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Details

Stereochemistry ACHIRAL
Molecular Formula C22H22FN5O3
Molecular Weight 423.4402
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPEBRUTINIB

SMILES

COCCOC1=CC=C(NC2=NC=C(F)C(NC3=CC(NC(=O)C=C)=CC=C3)=N2)C=C1

InChI

InChIKey=KXBDTLQSDKGAEB-UHFFFAOYSA-N
InChI=1S/C22H22FN5O3/c1-3-20(29)25-16-5-4-6-17(13-16)26-21-19(23)14-24-22(28-21)27-15-7-9-18(10-8-15)31-12-11-30-2/h3-10,13-14H,1,11-12H2,2H3,(H,25,29)(H2,24,26,27,28)

HIDE SMILES / InChI

Molecular Formula C22H22FN5O3
Molecular Weight 423.4402
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Spebrutinib (CC-292, AVL-292) is a selective inhibitor of BTK that was under clinical development for the treatment of rheumatoid arthritis (phase II) and B-cell Lymphoma (phase I). The drug was discovered by Avila Therapeutics, but then acquired by Celgene. Spebrutinib covalently binds to Cys 481 in BTK, blocking the ATP-binding pocket of the enzyme. The drug is no longer in Celgene's pipeline and its development is supposed to be terminated.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Tyrosine kinase inhibitors as potential drugs for B-cell lymphoid malignancies and autoimmune disorders.
2012 Jul
Inhibition of Btk with CC-292 provides early pharmacodynamic assessment of activity in mice and humans.
2013 Aug
Bruton's tyrosine kinase (BTK) inhibitors in clinical trials.
2014 Mar
Patents

Sample Use Guides

Patients should take oral spebrutinib in a dose of 375 mg daily (250 mg in the AM and 125 mg in the PM for 28 days).
Route of Administration: Oral
Cells from the Ramos lymphoma cell line, which expresses an intact BCR signaling pathway, were treated with increasing concentrations of spebrutinib for 1 hour and lysed, and the percent occupancy of BTK was determined with ELISA. The concentration of spebrutinib required for 50% occupancy was 5.9 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:23:16 GMT 2023
Edited
by admin
on Fri Dec 15 18:23:16 GMT 2023
Record UNII
DRU6NG543J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SPEBRUTINIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
3-(5-FLUORO-2-(4-(2-METHOXYETHOXY)PHENYLAMINO)PYRIMIDIN-4-YLAMINO)PHENYL)ACRYLAMIDE
Systematic Name English
CC-292
Code English
AVL-292
Code English
SPEBRUTINIB [USAN]
Common Name English
Spebrutinib [WHO-DD]
Common Name English
N-(3-((5-FLUORO-2-((4-(2-METHOXYETHOXY)PHENYL)AMINO)PYRIMIDIN-4-YL)AMINO)PHENYL)ACRYLAMIDE
Systematic Name English
spebrutinib [INN]
Common Name English
BTK INHIBITOR CC-292
Common Name English
2-PROPENAMIDE, N-(3-((5-FLUORO-2-((4-(2-METHOXYETHOXY)PHENYL)AMINO)-4-PYRIMIDINYL)AMINO)PHENYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C124801
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
NCI_THESAURUS C129825
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
FDA ORPHAN DRUG 408313
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
Code System Code Type Description
DRUG BANK
DB11764
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
SMS_ID
100000169951
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
NCI_THESAURUS
C97037
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
EVMPD
SUB183689
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL3301625
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID101026012
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
INN
10004
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
CAS
1202757-89-8
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
USAN
AB-94
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
FDA UNII
DRU6NG543J
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
PUBCHEM
59174488
Created by admin on Fri Dec 15 18:23:16 GMT 2023 , Edited by admin on Fri Dec 15 18:23:16 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY