New anticancer drug Genotoxicity Clinical trial Synthesis pathways Side Effects
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Neratinib

New anticancer drug Genotoxicity Clinical trial Synthesis pathways Side Effects
Neratinib Structure
Neratinib
  • CAS No.698387-09-6
  • Chemical Name:Neratinib
  • CBNumber:CB2855051
  • Molecular Formula:C30H29ClN6O3
  • Formula Weight:557.04
  • MOL File:698387-09-6.mol
Neratinib Property
  • Boiling point: :757.0±60.0 °C(Predicted)
  • Density  :1.33
  • form  :Off-white solid.
  • pka :12.37±0.43(Predicted)
  • FDA UNII :JJH94R3PWB
  • ATC code :L01EH02
Safety
  • HS Code  :29334900
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements
Neratinib Price More Price(4)
  • Brand: Cayman Chemical
  • Product number: 18404
  • Product name : Neratinib
  • Purity: ≥98%
  • Packaging: 1mg
  • Price: $35
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 18404
  • Product name : Neratinib
  • Purity: ≥98%
  • Packaging: 5mg
  • Price: $114
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 18404
  • Product name : Neratinib
  • Purity: ≥98%
  • Packaging: 10mg
  • Price: $193
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 18404
  • Product name : Neratinib
  • Purity: ≥98%
  • Packaging: 25mg
  • Price: $263
  • Updated: 2021/03/22
  • Buy: Buy

Neratinib Chemical Properties,Usage,Production

  • New anticancer drug Neratinib developed by US Wyeth company is an irreversible epidermal growth factor receptor(EGFR) inhibitor. It is a multiple target point of small molecule tyrosine kinase inhibitors to HER 2 and HER1 after Lapatinib, and is an irreversible ErbB receptor tyrosine kinase inhibitor. Neratinib could selectively inhibit HER-1 and HER-2 of EGFR family(IC50 was 92 nmol/L and 59 nmol/L, respectively). Clinical research showed that Neratinib exerted significant therapeutic effect on non-small cell lung cancer, colon cancer, and breast cancer.
    The phaseⅡclinical trial indicated that Neratinib showed good efficacy and tolerance to HER-2 positive patients with advanced breast cancer who had been received or not Trastuzumab treatment.
    The phase Ⅲ breast cancer clinical trial was complete in September 2014. The data indicated that the efficacy of Neratinib was better than Roche's Herceptin in treatment of HER-2 positive early breast cancer.
    The above information is edited by the Chemicalbook of Liu Yujie.
  • Genotoxicity

    Neratinib and its metabolites were not genotoxic. Administration of neratinib to pregnant rabbits during organogenesis resulted in abortions, embryo-fetal death, and fetal abnormalities at maternal exposures (AUC) approximately 0.2 times exposures in patients at the recommended dose. Oral administration of neratinib to pregnant rats from gestation day 7 until lactation day 20 resulted in effects on long-term memory in male offspring at maternal doses less than the maximum recommended clinical dose on a mg/m2 basis. Neratinib was not carcinogenic in a 26-week carcinogenicity study in rasH2 transgenic mice.

  • Clinical trial

    Neratinib was tested in a phase II trial as monotherapy in 2 cohorts of patients with advanced HER2-positive breast cancer those with and those without previous trastuzumab treatment. Sixteen-week progression-free survival (PFS) rates were 59% for patients with previous trastuzumab treatment and 78% for patients with no previous trastuzumab treatment with a median PFS of 22.3 and 39.6 weeks, respectively. Objective response rates were 24% among patients with previous trastuzumab treatment and 56% in the trastuzumab-naive cohort.[4]

  • Synthesis pathways 3-chloro-4-(pyridin-2-yl-methoxy)-aniline (2) and N-(4-chloro-3-cyano-7-ethoxy-quinolin-6-yl)-acetamide (3) are used as raw material to prepare N-[4-[3-chloro-4-(pyridin-2-yl-methoxy) anilino]-3-cyano-7-ethoxy-quinolin-6-yl] acetamide (4) by nucleophilic substitution. Deprotection of 4 was under the effect of hydrochloric acid, then was precipitated the free base in methanol solution of potassium carbonate to prepare 6-amino-3-cyano-4-[3-chloro-4-(pyridin-2-yl-methoxy) anilino]-7-ethoxy-quinoline (5). Neratinib(1) was obtained by condensation of 5 and acyl chloride which was prepared by trans-4-dimethylamino-crotonic acid hydrochloride (6).
    Synthesis pathways of Neratinib
    Figure 1 Synthesis pathways of Neratinib
  • Side Effects Diarrhea, nausea, vomiting, and fatigue.
  • Uses Neratinib (HKI-272) is a highly selective HER2 and EGFR inhibitor with IC50 of 59 nM and 92 nM, respectively.
  • Uses An oral, irreversible dual EGFR/HER2 inhibitor for breast and non-small cell lung cancer. Antitumor agent
  • Definition ChEBI: A quinoline compound having a cyano group at the 3-position, a 3-chloro-4-(2-pyridylmethoxy)anilino group at the 4-position, a 4-dimethylamino-trans-but-2-enamido group at the 6-position, and an ethoxy group at the 7-position.
Neratinib Preparation Products And Raw materials
Raw materials
Preparation Products
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Related articles
698387-09-6, NeratinibRelated Search:
  • (2e)-n-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide
  • Neratinib(HKI-272)
  • (2E)-N-[4-[[3-chloro-4-(2-pyridinylMethoxy)phenyl]aMino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(diMethylaMino)-2-butenaMide
  • neratinib
  • (E)-N-[4-[3-Chloro-4-[(2-pyridinyl)methoxy]anilino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide
  • N-(4-(3-Chloro-4-(2-pyridinylmethoxy)anilino)-3-cyano-7-ethoxy-6-quinolyl)-4-(dimethylamino)-2-butenamide
  • Unii-jjh94R3pwb
  • HKI-272; HKI272; HKI 272
  • CS-26
  • (2e)-n-(4-((3-chloro-4-((pyridin-2-yl)Methoxy)phenyl)aMino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(diMethylaMino)but-2-enaMide neratinib
  • HKI-272 Neratinib
  • Neratinib HKI-272 (2E)-N-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide
  • Neratinib (2E)-N-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide
  • (2E)-N-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-emide
  • PB272(neratinib)
  • 2-ButenaMide,N-[4-[[3-chloro-4-(2-pyridinylMethoxy)phenyl]aMino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(diMethylaMino)-,(2E)-
  • Neratinib, >=99%
  • PB-272
  • PF-0528767
  • WAY-179272
  • (E)-N-(4-(3-Chloro-4-(pyridin-2-yLmethoxy)phenylamino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimet
  • Neratinib API and intermediates
  • Neratinib, 99%, a highly selective HER2 and EGFR inhibitor
  • nevatinib
  • 101028
  • Lenatinib Impurity E
  • Neratinib USP/EP/BP
  • 698387-09-6
  • 688387-09-6
  • C30H29ClN6O3
  • C30H31ClN6O2
  • Inhibitors
  • Anti-cancer & immunity
  • Antineoplastic
  • API