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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H23N7O2
Molecular Weight 465.5065
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACALABRUTINIB

SMILES

CC#CC(=O)N1CCC[C@H]1C2=NC(=C3N2C=CN=C3N)C4=CC=C(C=C4)C(=O)NC5=CC=CC=N5

InChI

InChIKey=WDENQIQQYWYTPO-IBGZPJMESA-N
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

HIDE SMILES / InChI
Molecular Formula C26H23N7O2
Molecular Weight 465.5065
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:01:59 UTC 2023
Edited
by admin
on Sat Dec 16 10:01:59 UTC 2023
Record UNII
I42748ELQW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACALABRUTINIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
ACALABRUTINIB [JAN]
Common Name English
ACP-196
Code English
ACALABRUTINIB [ORANGE BOOK]
Common Name English
BENZAMIDE, 4-(8-AMINO-3-((2S)-1-(1-OXO-2-BUTYN-1-YL)-2-PYRROLIDINYL)IMIDAZO(1,5-A)PYRAZIN-1-YL)-N-2-PYRIDINYL-
Systematic Name English
Acalabrutinib [WHO-DD]
Common Name English
acalabrutinib [INN]
Common Name English
ACALABRUTINIB [USAN]
Common Name English
ACALABRUTINIB [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 477415
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
NCI_THESAURUS C124801
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
NDF-RT N0000175605
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
EU-Orphan Drug EU/3/16/1625
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
FDA ORPHAN DRUG 489015
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
FDA ORPHAN DRUG 488915
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
Code System Code Type Description
DAILYMED
I42748ELQW
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
DRUG BANK
DB11703
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
NCI_THESAURUS
C113442
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
CAS
1639823-20-3
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
SUPERSEDED
CAS
1420477-60-6
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
EVMPD
SUB182073
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
SMS_ID
100000168547
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
FDA UNII
I42748ELQW
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
MERCK INDEX
m12069
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
LACTMED
Acalabrutinib
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID401026209
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
WIKIPEDIA
Acalabrutinib
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
RXCUI
1986808
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
PUBCHEM
71226662
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
ChEMBL
CHEMBL3707348
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
INN
10150
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
USAN
DE-48
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
DRUG CENTRAL
5260
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
CHEBI
167707
Created by admin on Sat Dec 16 10:02:00 UTC 2023 , Edited by admin on Sat Dec 16 10:02:00 UTC 2023
PRIMARY
Related Record Type Details
Structure of Acalabrutinib, (R)-
ENANTIOMER -> ENANTIOMER
Structure of ACALABRUTINIB DIHYDRATE
SOLVATE->ANHYDROUS
Structure of ACALABRUTINIB
EXCRETED UNCHANGED
In the mass balance study, 84% of the dose was received in the feces and 12% of the dose was recovered in the urine, with less than 1% of the dose excreted as unchanged acalabrutinib in urine.
AMOUNT EXCRETED
URINE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
TYROSINE-PROTEIN KINASE BTK
TARGET -> INHIBITOR
Acalabrutinib forms a covalent bond with Cys481 in the BTK adenosine triphosphate (ATP).
IRREVERSIBLE INHIBITOR
IC50
Structure of ACALABRUTINIB DIHYDRATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
POTASSIUM VOLTAGE-GATED CHANNEL SUBFAMILY H MEMBER 2
OFF TARGET->NON-INHIBITOR
IC50
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
Structure of ACALABRUTINIB MALEATE MONOHYDRATE
SALT/SOLVATE -> PARENT
Structure of ACALABRUTINIB MALEATE ANHYDROUS
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of (2R)-2-AMINO-3-((E)-3-((2S)-2-(8-AMINO-1-(4-(2-PYRIDYLCARBAMOYL)PHENYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)PYRROLIDIN-1-YL)-1-METHYL-3-OXO-PROP-1-ENYL)SULFANYL-PROPANOIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of 4-(2-((2S)-1-BUT-2-YNOYLPYRROLIDIN-2-YL)-5-CARBAMIMIDOYL-1H-IMIDAZOL-4-YL)-N-(2-PYRIDYL)BENZAMIDE
METABOLITE -> PARENT
Structure of 4-(8-AMINO-3-(1-BUT-2-YNOYL-2,3-DIHYDROPYRROL-5-YL)IMIDAZO(1,5-A)PYRAZIN-1-YL)-N-(2-PYRIDYL)BENZAMIDE
METABOLITE -> PARENT
PLASMA
Structure of (2S)-2-AMINO-5-(((1R)-1-(((E)-3-((2S)-2-(8-AMINO-1-(4-(2-PYRIDYLCARBAMOYL)PHENYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)PYRROLIDIN-1-YL)-1-METHYL-3-OXO-PROP-1-ENYL)SULFANYLMETHYL)-2-(CARBOXYMETHYLAMINO)-2-OXO-ETHYL)AMINO)-5-OXO-PENTANOIC ACID
METABOLITE -> PARENT
Structure of 2-(((2R)-2-AMINO-3-((E)-3-((2S)-2-(8-AMINO-1-(4-(2-PYRIDYLCARBAMOYL)PHENYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)PYRROLIDIN-1-YL)-1-METHYL-3-OXO-PROP-1-ENYL)SULFANYL-PROPANOYL)AMINO)ACETIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of 4-(8-AMINO-3-((2S)-1-BUT-2-YNOYLPYRROLIDIN-2-YL)IMIDAZO(1,5-A)PYRAZIN-1-YL)BENZOIC ACID
METABOLITE -> PARENT
Structure of 4-(8-AMINO-3-((2S)-1-(3-HYDROXYBUTANOYL)PYRROLIDIN-2-YL)IMIDAZO(1,5-A)PYRAZIN-1-YL)-N-(2-PYRIDYL)BENZAMIDE
METABOLITE -> PARENT
FECAL
Structure of 4-[8-amino-3-[(2S)-1-(3-oxobutanoyl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide
METABOLITE -> PARENT
FECAL
Structure of ACP-5825
METABOLITE -> PARENT
Structure of 4-(8-AMINO-1-(4-(2-PYRIDYLCARBAMOYL)PHENYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)-4-OXO-BUTANOIC ACID
METABOLITE -> PARENT
PLASMA
Structure of 4-(8-AMINO-3-(4-(BUT-2-YNOYLAMINO)BUTANOYL)IMIDAZO(1,5-A)PYRAZIN-1-YL)BENZOIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of Acalabrutinib, (R)-
IMPURITY -> PARENT
Related Record Type Details
Structure of ACALABRUTINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
SOLUBILITY CHEMICAL
Structure of WATER
pH
CHEMICAL
Volume of Distribution PHARMACOKINETIC
SOLUBILITY CHEMICAL
Structure of WATER
pH
CHEMICAL
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966