Neratinib

Name: Neratinib
Brand: SIGMA

≥98% (HPLC), powder, pan-HER inhibitor

Synonym(e):

(2E)-N-[4-[[3-Chloro-4-(2-pyridinylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide, 4-Dimethylamino-but-2-enoic acid {4-[3-chloro-4-(pyridin-2-ylmethoxy)phenylamino]-3-cyano-7-ethoxy-quinolin-6-yl}-amide, (E)-N-[4-[3-Chloro-4-[(2-pyridinyl)methoxy]anilino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide, (E)-N-[4-[[3-Chloro-4-((pyridin-2-yl)methoxy)phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)-2-butenamide, HKI-272, HKI 272

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Über diesen Artikel

Empirische Formel (Hill-System):

C₃₀H₂₉ClN₆O₃

CAS-Nummer:

698387-09-6

Molekulargewicht:

557.04

MDL number:

MFCD09752958

NACRES:

NA.21

Assay:

≥98% (HPLC)

Form:

powder

Preise und Verfügbarkeit sind derzeit nicht verfügbar.

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Eigenschaften

Quality Segment

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CN(C)C/C=C/C(NC(C=C1C(NC2=CC(Cl)=C(C=C2)OCC3=NC=CC=C3)=C4C#N)=C(C=C1N=C4)OCC)=O

Beschreibung

General description

Neratinib is a compound featuring a quinolone core, with a lipophilic 2-pyridinylmethyl moiety at the para-position of the aniline and a lipophilic chlorine atom at the meta-position. These structural elements enhance its activity against human epidermal growth factor receptor 2 (HER2).

Application

Neratinib may be used to study its anti-proliferative effects in gastric adenocarcinoma cells.

Biochem/physiol Actions

Irreversible pan-HER inhibitor, covalently targets EGFR/HER2/HER4, providing sustained signaling blockade and clinical benefit in HER2-positive breast cancer.

Neratinib (HKI-272), an oral, potent, irreversible pan-HER tyrosine kinase inhibitor, targets EGFR, HER2, and HER4 by covalently binding specific cysteine residues (Cys773/EGFR, Cys805/HER2) within the ATP-binding pocket. This mechanism provides prolonged target inhibition, effectively blocking HER phosphorylation (IC50 ~3-5 nM) and downstream MAPK/Akt signaling (IC50 ~2 nM). Consequently, it reduces cyclin D1/Rb phosphorylation (IC50 ~9 nM) and induces G1-S arrest and apoptosis in sensitive cell lines (e.g., BT474, SKBr3, A431) at low nM concentrations, underpinning its use against HER2-driven cancers.

Neratinib (HKI-272), an oral, potent, irreversible pan-HER tyrosine kinase inhibitor, targets EGFR, HER2, and HER4 by covalently binding specific cysteine residues (Cys773/EGFR, Cys805/HER2) within the ATP-binding pocket. This mechanism provides prolonged target inhibition, effectively blocking HER phosphorylation (IC50 ~3-5 nM) and downstream MAPK/Akt signaling (IC50 ~2 nM). Consequently, it reduces cyclin D1/Rb phosphorylation (IC50 ~9 nM) and induces G1-S arrest and apoptosis in sensitive cell lines (e.g., BT474, SKBr3, A431) at low nM concentrations, underpinning its use against HER2-driven cancers.