CHEBI:167707 - acalabrutinib

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ChEBI Name acalabrutinib
ChEBI ID CHEBI:167707
Definition A member of the class of imidazopyrazines that is imidazo[1,5-a]pyrazine substituted by 4-(pyridin-2-ylcarbamoyl)phenyl, (2S)-1-(but-2-ynoyl)pyrrolidin-2-yl, and amino groups at positions 1, 3 and 8, respectively. It is an irreversible second-generation Bruton's tyrosine kinase (BTK) inhibitor that is approved by the FDA for the treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
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Formula C26H23N7O2
Net Charge 0
Average Mass 465.517
Monoisotopic Mass 465.19132
InChI InChI=1S/C26H23N7O2/c1-2-6-21(34)32-15-5-7-19(32)25-31-22(23-24(27)29-14-16-33(23)25)17-9-11-18(12-10-17)26(35)30-20-8-3-4-13-28-20/h3-4,8-14,16,19H,5,7,15H2,1H3,(H2,27,29)(H,28,30,35)/t19-/m0/s1
InChIKey WDENQIQQYWYTPO-IBGZPJMESA-N
SMILES [H][C@]1(CCCN1C(=O)C#CC)C1=NC(=C2N1C=CN=C2N)C1=CC=C(C=C1)C(=O)NC1=CC=CC=N1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acalabrutinib (CHEBI:167707) has role antineoplastic agent (CHEBI:35610)
acalabrutinib (CHEBI:167707) has role apoptosis inducer (CHEBI:68495)
acalabrutinib (CHEBI:167707) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
acalabrutinib (CHEBI:167707) is a aromatic amine (CHEBI:33860)
acalabrutinib (CHEBI:167707) is a benzamides (CHEBI:22702)
acalabrutinib (CHEBI:167707) is a imidazopyrazine (CHEBI:37847)
acalabrutinib (CHEBI:167707) is a pyridines (CHEBI:26421)
acalabrutinib (CHEBI:167707) is a pyrrolidinecarboxamide (CHEBI:46770)
acalabrutinib (CHEBI:167707) is a secondary carboxamide (CHEBI:140325)
acalabrutinib (CHEBI:167707) is a tertiary carboxamide (CHEBI:140326)
acalabrutinib (CHEBI:167707) is a ynone (CHEBI:51723)
IUPAC Name
4-{8-amino-3-[(2S)-1-(but-2-ynoyl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide
INNs Sources
acalabrutinib WHO MedNet
acalabrutinib WHO MedNet
acalabrutinib WHO MedNet
acalabrutinibum WHO MedNet
Synonyms Sources
(S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide ChEBI
4-[8-amino-3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-(2-pyridyl)benzamide ChEBI
ACP-196 ChemIDplus
Brand Name Source
Calquence ChemIDplus
Manual Xrefs Databases
36764951 ChemSpider
5260 DrugCentral
Acalabrutinib Wikipedia
D10893 KEGG DRUG
DB11703 DrugBank
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Registry Number Type Source
1420477-60-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 March 2021