SPEBRUTINIB

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27471698 | https://clinicaltrials.gov/ct2/show/NCT01975610 | http://ir.celgene.com/releasedetail.cfm?releaseid=795895

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein kinase BTK 24 Target ID: CHEMBL5251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23709115	Inhibitor 8297		5.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://clinicaltrials.gov/ct2/show/NCT01975610	Palliative		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003AN8	https://www.1pchem.com/search?query=1P003AN8
AA Blocks	AA003A3S	http://aablocks.com/goods/Goods/detail?id=AA003A3S
AChemBlock	H-8741	http://www.achemblock.com/catalogsearch/result/?q=H-8741
AK Scientific	2235AH	https://aksci.com/item_detail.php?cat=2235AH
AK Scientific	SYN5695	https://aksci.com/item_detail.php?cat=SYN5695
AOBIOUS INC	AOB87153	http://aobious.com/aobious/search?search_query=AOB87153
AbovChem LLC	HY-18012A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-18012A
Ambeed	A537377	http://www.ambeed.com/search/Search.html?keyword=A537377
Angene	AGN-PC-0WAKN6	http://www.angenechemical.com/productshow/AGN-PC-0WAKN6.html
ApexBio Technology	A3206	https://www.apexbt.com/catalogsearch/result/?q=A3206
AstaTech	42169	http://astatechinc.com/CPSResult.php?CRNO=42169
Axon MedChem	2226	https://www.axonmedchem.com/product/2226
BLD Pharm	BD328411	http://www.bldpharm.com/search/Search.html?keyword=BD328411
BLD Pharm	BD630181	http://www.bldpharm.com/search/Search.html?keyword=BD630181
Capot Chemical	2692	https://www.capotchem.com/search.do?q=2692
Cayman Chemical	17993	http://www.caymanchem.com/app/template/Product.vm/catalog/17993
Chem Scene	CS-1482	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1482
ChemShuttle	125000	https://www.chemshuttle.com/catalogsearch/result/?q=125000
Combi-Blocks	QJ-1395	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-1395
Debye Scientific	DA-35316	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-35316
Excenen	EX-A255	http://www.excenen.com/searchresultlist.php?id=EX-A255
KeyOrganics	AS-16998	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16998
Lab Seeker	SC-94180	http://www.labseeker.com/search.php?keywords=SC-94180&category=0
LabSeeker	SC-94180	http://www.labseeker.com/search.php?keywords=SC-94180&category=0
Matrix Scientific	148415	http://www.matrixscientific.com/148415.html
MedChem Express	HY-18012	https://www.medchemexpress.com/search.html?q=HY-18012&ft=&fa=&fp=
MolPort	MolPort-028-720-820	https://www.molport.com/shop/molecule-link/MolPort-028-720-820
Molnova	M10735	https://www.molnova.com/en/serch-list.html?keywords=M10735
Molnova	M11478	https://www.molnova.com/en/serch-list.html?keywords=M11478
MuseChem	441	https://www.musechem.com/product/441.html
MuseChem	I000746	https://www.musechem.com/product/I000746.html
Ryan Scientific	101-94185	https://ryansci.com/products?q=101-94185&list_q=&search_type=exact
Ryan Scientific	RN486	https://ryansci.com/products?q=RN486&list_q=&search_type=exact
Selleck Chemicals	S7173	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7173
ShangHai Biochempartner	BCP000890	http://www.biochempartner.com/search_BCP000890
ShangHai Biochempartner	BCP07702	http://www.biochempartner.com/search_BCP07702
ShangHai Biochempartner	BCP16838	http://www.biochempartner.com/search_BCP16838
Synovel	SN-0090	http://www.synovellab.com/?s=SN-0090&submit=Search
TargetMol	T2603	https://www.targetmol.com/search?keyword=T2603
Toronto Research Chemicals	A794715	https://www.trc-canada.com/product-detail/?CatNum=A794715
Toronto Research Chemicals	T795133	https://www.trc-canada.com/product-detail/?CatNum=T795133
eMolecules	252348624	https://orderbb.emolecules.com/search/#?query=252348624
eMolecules	46339059	https://orderbb.emolecules.com/search/#?query=46339059
eMolecules	50284139	https://orderbb.emolecules.com/search/#?query=50284139
eNovation Chemicals	D572704	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D572704&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4788692981	https://mcule.com/MCULE-4788692981/
mcule	MCULE-5639095348	https://mcule.com/MCULE-5639095348/

PubMed

Title	Date	PubMed
Phase I study of single-agent CC-292, a highly selective Bruton's tyrosine kinase inhibitor, in relapsed/refractory chronic lymphocytic leukemia.	2016 Jul	27151992

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 UTC 2023` Edited by `admin` on `Fri Dec 15 18:23:16 UTC 2023`
Record UNII	DRU6NG543J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPEBRUTINIB

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