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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H24N6O2
Molecular Weight 440.4971
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBRUTINIB

SMILES

NC1=C2C(=NC=N1)N(N=C2C3=CC=C(OC4=CC=CC=C4)C=C3)[C@@H]5CCCN(C5)C(=O)C=C

InChI

InChIKey=XYFPWWZEPKGCCK-GOSISDBHSA-N
InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1

HIDE SMILES / InChI
Molecular Formula C25H24N6O2
Molecular Weight 440.4971
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 Fri Dec 15 20:18:17 UTC 2023
Edited
by admin
on Fri Dec 15 20:18:17 UTC 2023
Record UNII
1X70OSD4VX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IBRUTINIB
DASH   INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
Ibrutinib [WHO-DD]
Common Name English
PCI-32765
Code English
PCI-32765-00
Code English
IBRUTINIB [VANDF]
Common Name English
IMBRUVICA
Brand Name English
IBRUTINIB [ORANGE BOOK]
Common Name English
2-PROPEN-1-ONE, 1-((3R)-3-(4-AMINO-3-(4-PHENOXYPHENYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-1-YL)-1-PIPERIDINYL)-
Systematic Name English
IBRUTINIB [JAN]
Common Name English
IBRUTINIB [USAN]
Common Name English
IBRUTINIB [MI]
Common Name English
PC-32765
Code English
PCI 32765
Code English
1-{(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1- yl}prop-2-en-1-one
Systematic Name English
CRA-032765
Code English
ibrutinib [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 462314
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 574317
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
EMA ASSESSMENT REPORTS IMBRUVIA (AUTHORIZED: LYMPHOMA, MANTLE-CELL)
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 622317
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 409713
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 462214
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 444414
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
EMA ASSESSMENT REPORTS IMBRUVICA (AUTHORIZED: LEUKEMIA, LYMPHOCYTIC, CHRONIC, B-CELL)
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 407413
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
NCI_THESAURUS C124801
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
EU-Orphan Drug EU/3/13/1203
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
WHO-ATC L01XE27
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 395513
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 525616
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 383112
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
NDF-RT N0000175605
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 462114
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 366212
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 368012
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
FDA ORPHAN DRUG 397313
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
NCI_THESAURUS C129825
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
Code System Code Type Description
WIKIPEDIA
Ibrutinib
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID60893450
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
INN
9566
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
SMS_ID
100000144394
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
EU-Orphan Drug
EU/3/12/984(POSITIVE)
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY On 26 April 2012, orphan designation (EU/3/12/984) was granted by the European Commission to Nexus Oncology Ltd, United Kingdom, for 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4 d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one for the treatment of chronic lymphocytic leukaemia. The sponsorship was transferred to Janssen-Cilag International N.V, Belgium, in January 2013.
CHEBI
76612
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
USAN
YY-102
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
DRUG BANK
DB09053
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
DAILYMED
1X70OSD4VX
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
FDA UNII
1X70OSD4VX
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
MERCK INDEX
m11677
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
LACTMED
Ibrutinib
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
IUPHAR
6912
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL1873475
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
NCI_THESAURUS
C81934
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
DRUG CENTRAL
4810
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
RXCUI
1442981
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY RxNorm
PUBCHEM
24821094
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
EVMPD
SUB120863
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
CAS
936563-96-1
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
HSDB
8260
Created by admin on Fri Dec 15 20:18:17 UTC 2023 , Edited by admin on Fri Dec 15 20:18:17 UTC 2023
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
TYROSINE-PROTEIN KINASE BTK C481S (IBRUTINIB RESISTANT MUTANT)
TARGET -> INHIBITOR RESISTANT
Structure of IBRUTINIB
PROTEIN ADDUCT FORMATION
TYROSINE-PROTEIN KINASE BTK
TARGET -> INHIBITOR
Binds to a cysteine residue (Cys-481) in the BTK active site
IRREVERSIBLE INHIBITOR
IC50
TYROSINE-PROTEIN KINASE ITK/TSK
OFF-TARGET->INHIBITOR
Structure of IBRUTINIB
EXCRETED UNCHANGED
FECAL
EPIDERMAL GROWTH FACTOR RECEPTOR
OFF-TARGET->INHIBITOR
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2
OFF-TARGET->INHIBITOR
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-4
OFF-TARGET->INHIBITOR
Structure of IBRUTINIB, (S)-
ENANTIOMER -> ENANTIOMER
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of PCI-45752
METABOLITE -> PARENT
Structure of PCI-45227
METABOLITE ACTIVE -> PARENT
Concentration higher than IBRUTINIB
MAJOR
PLASMA
Structure of N-(2-(4-AMINO-3-(4-PHENOXYPHENYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-1-YL)-5-HYDROXYPENTYL)-2,3-DIHYDROXYPROPANAMIDE, (R)-
METABOLITE -> PARENT
Structure of PCI-45741
METABOLITE -> PARENT
Structure of PCI-45227
METABOLITE ACTIVE -> PARENT
FECAL
Related Record Type Details
Structure of IBRUTINIB N-DESACRYLOYL IMPURITY
IMPURITY -> PARENT
Structure of 1-PROPANONE, 1,3-BIS((3R)-3-(4-AMINO-3-(4-PHENOXYPHENYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-1-YL)-1-PIPERIDINYL)-
IMPURITY -> PARENT
Structure of IBRUTINIB CHLORO IMPURITY
IMPURITY -> PARENT
Related Record Type Details
Structure of IBRUTINIB
ACTIVE MOIETY
FECAL
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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