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Details

Stereochemistry ACHIRAL
Molecular Formula C30H29ClN6O3
Molecular Weight 557.043
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NERATINIB

SMILES

CCOC1=C(NC(=O)\C=C\CN(C)C)C=C2C(=C1)N=CC(C#N)=C2NC3=CC=C(OCC4=NC=CC=C4)C(Cl)=C3

InChI

InChIKey=JWNPDZNEKVCWMY-VQHVLOKHSA-N
InChI=1S/C30H29ClN6O3/c1-4-39-28-16-25-23(15-26(28)36-29(38)9-7-13-37(2)3)30(20(17-32)18-34-25)35-21-10-11-27(24(31)14-21)40-19-22-8-5-6-12-33-22/h5-12,14-16,18H,4,13,19H2,1-3H3,(H,34,35)(H,36,38)/b9-7+

HIDE SMILES / InChI
Molecular Formula C30H29ClN6O3
Molecular Weight 557.043
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:25:26 UTC 2023
Edited
by admin
on Fri Dec 15 16:25:26 UTC 2023
Record UNII
JJH94R3PWB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NERATINIB
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
2-BUTENAMIDE, N-(4-((3-CHLORO-4-(2-PYRIDINYLMETHOXY)PHENYL)AMINO)-3-CYANO-7-ETHOXY-6-QUINOLINYL)-4-(DIMETHYLAMINO)-, (2E)-
Systematic Name English
HKI-272
Code English
CDP-820
Code English
NERATINIB [MART.]
Common Name English
NERATINIB [MI]
Common Name English
NERATINIB [USAN]
Common Name English
neratinib [INN]
Common Name English
Neratinib [WHO-DD]
Common Name English
(2E)-N-[4-[[3-Chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
FDA ORPHAN DRUG 699119
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
NCI_THESAURUS C129825
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
WHO-ATC L01XE45
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
NDF-RT N0000175605
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
Code System Code Type Description
WIKIPEDIA
NERATINIB
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL180022
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
PUBCHEM
9915743
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
DRUG CENTRAL
5252
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
CHEBI
61397
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
EVMPD
SUB32232
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID70220132
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
DRUG BANK
DB11828
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
INN
8878
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
FDA UNII
JJH94R3PWB
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
RXCUI
1940643
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
CAS
698387-09-6
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
NCI_THESAURUS
C49094
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
MERCK INDEX
m7827
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY Merck Index
DAILYMED
JJH94R3PWB
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
USAN
SS-120
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
CAS
876310-02-0
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
SMS_ID
100000124443
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
LACTMED
Neratanib
Created by admin on Fri Dec 15 16:25:26 UTC 2023 , Edited by admin on Fri Dec 15 16:25:26 UTC 2023
PRIMARY
Related Record Type Details
SUBSTANCE-P RECEPTOR
OFF-TARGET->INHIBITOR
INHIBITOR
Percent inhibition of specific binding
Structure of NERATINIB MALEATE ANHYDROUS
SALT/SOLVATE -> PARENT
BT-474
CELL->INHIBITOR
CELL PROLIFERATION
IC50
Structure of NERATINIB MALEATE MONOHYDRATE
SALT/SOLVATE -> PARENT
PLATELET-ACTIVATING FACTOR RECEPTOR
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2
TARGET -> INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
NEUROMEDIN-K RECEPTOR
TARGET -> INHIBITOR
Radioligand binding assay
BINDING
IC50
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
ex vivo protein binding of neratinib in human plasma samples from clinical study in healthy subjects as determined using ult racentrifugation was 88%
BINDING
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
OFF-TARGET->INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2 D769Y MUTANT
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
IC50
HISTAMINE H3 RECEPTOR
OFF-TARGET->INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
Structure of NERATINIB
CUMULATIVE EXCRETION
URINE
OXYTOCIN RECEPTOR
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
OXYTOCIN RECEPTOR
TARGET -> INHIBITOR
Neratinib concentration at 10 microM
Percent inhibition of specific binding
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2 V777L MUTANT
TARGET -> INHIBITOR
± 4.37
IRREVERSIBLE INHIBITOR
IC50
HISTAMINE H2 RECEPTOR
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
G1/S-SPECIFIC CYCLIN-D1
TARGET -> INHIBITOR
Cyclin D1 expression in BT474 cells
INHIBITOR
IC50
SK-BR-3
CELL->INHIBITOR
CELL PROLIFERATION
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-4
TARGET -> INHIBITOR
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2
TARGET -> INHIBITOR
HER2 ligand-independent receptor phosphorylation in BT474
IRREVERSIBLE INHIBITOR
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2 R896C MUTANT
TARGET -> INHIBITOR
IRREVERSIBLE INHIBITOR
IC50
EPIDERMAL GROWTH FACTOR RECEPTOR
TARGET -> INHIBITOR
IC50
MUSCARINIC ACETYLCHOLINE RECEPTOR M2
OFF-TARGET->INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
VASOPRESSIN V1A RECEPTOR
TARGET -> INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
MUSCARINIC ACETYLCHOLINE RECEPTOR M3
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2 D769H MUTANT
TARGET -> INHIBITOR
IC50
EPIDERMAL GROWTH FACTOR RECEPTOR
TARGET -> INHIBITOR
EGFR-dependent receptor phosphorylation in A431 cells
IC50
HISTAMINE H3 RECEPTOR
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> NON-INDUCER
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
SUBSTANCE-P RECEPTOR
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
VASOPRESSIN V1A RECEPTOR
OFF-TARGET->INHIBITOR
Radioligand binding assay
BINDING
IC50
MUSCARINIC ACETYLCHOLINE RECEPTOR M2
TARGET -> INHIBITOR
SUBSTANCE-K RECEPTOR
OFF-TARGET->INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
NEUROMEDIN-K RECEPTOR
TARGET -> INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
CYTOCHROME P450 3A4
METABOLIC ENZYME -> NON-INHIBITOR
IC50
EPIDERMAL GROWTH FACTOR RECEPTOR
TARGET -> INHIBITOR
IC50
RECEPTOR TYROSINE-PROTEIN KINASE ERBB-2
TARGET -> INHIBITOR
IC50
Structure of NERATINIB
CUMULATIVE EXCRETION
FECAL
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
In vitro, neratinib was highly bound (N 99 %) to human plasma proteins at clinical exposures. click to edit
BINDING
PLATELET-ACTIVATING FACTOR RECEPTOR
TARGET -> INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
HISTAMINE H2 RECEPTOR
TRANSPORTER -> INHIBITOR
Neratinib concentration at 10 microM
INHIBITOR
Percent inhibition of specific binding
SUBSTANCE-K RECEPTOR
TARGET -> INHIBITOR
Radioligand binding assay
BINDING
IC50
Related Record Type Details
Structure of NERATINIB PYRIDINE N-OXIDE
METABOLITE LESS ACTIVE -> PARENT
Structure of NERATINIB PYRIDINE N-OXIDE
METABOLITE ACTIVE -> PARENT
Structure of N-DESMETHYL NERATINIB
METABOLITE ACTIVE -> PARENT
Inhibition of HER2 kinase activity (in autophosphorylation assay; Neratinib IC50 = 39 nM)
INHIBITOR
IC50
Structure of NERATINIB DIMETHYLAMINE N-OXIDE
METABOLITE LESS ACTIVE -> PARENT
IC50 for HER2 kinase activity was up to 19 fold higher when compared to neratinib.
INHIBITOR
IC50
Related Record Type Details
Structure of NERATINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC Dose
PHARMACOKINETIC
Route of Administration
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC Route of Administration
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Dose
PHARMACOKINETIC
Route of Administration
PHARMACOKINETIC
Cmax PHARMACOKINETIC Dose
PHARMACOKINETIC
Route of Administration
PHARMACOKINETIC
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