Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00463)
Name
Neratinib
Synonyms    Click to Show/Hide the Synonyms of This API
Neratinib; 698387-09-6; HKI-272; Neratinib (HKI-272); Nerlynx; HKI 272; Neratinib(HKI-272); UNII-JJH94R3PWB; PB-272; JJH94R3PWB; (2E)-N-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide; CHEMBL180022; 698387-09-6 (free base); WAY-179272; (E)-N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide; C30H29ClN6O3; N-(4-(3-Chloro-4-(2-pyridinylmethoxy)anilino)-3-cyano-7-ethoxy-6-quinolyl)-4-(dimethylamino)-2-butenamide; (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-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide; (2E)-N-[4-[[3-Chloro-4-(2-pyridinylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide; (E)-N-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide; Neratinib [USAN:INN]; (E)-N-(4-((3-Chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide; PB 272; Neratinib HKI 272; PubChem22399; Tube708; Neratinib (USAN/INN); Neratinib - HKI-272; SCHEMBL571762; SCHEMBL571763; GTPL5686; CHEBI:61397; CDP-820; DTXSID70220132; EX-A062; QCR-104; SYN1140; Neratinib(HKI-272)/HKI272; BCPP000151; 876310-02-0; AOB87125; ZINC3916214; ABP000871; BDBM50161957; MFCD09752958; NSC757439; NSC800803; WAY-179272-B; AKOS005146340; AKOS025149637; BCP9000984; CCG-270036; DB11828; NSC-757439; NSC-800803; SB16595; NCGC00241101-01; NCGC00241101-03; NCGC00241101-09; AC-25073; AS-16279; HY-32721; AB0008022; EC-000.2260; A25338; D08950; Z-3202; 387N096; Q-101402; Q6995920; BRD-K85606544-001-01-8; (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;HKI-272; (E)-4-Dimethylamino-but-2-enoic acid {4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-3-cyano-7-ethoxy-quinolin-6-yl}-amide; 2-Butenamide, N-(4-((3-chloro-4-(2-pyridinylmethoxy)phenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-, (2E)-; 4-Dimethylamino-but-2-enoic acid {4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-3-cyano-7-ethoxy-quinolin-6-yl}-amide; N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide; N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)butanamide
Clinical Status
Approved
Disease Indication Breast cancer ICD-11: 2C60 [1]
PubChem CID
9915743
Formula
C30H29ClN6O3
Canonical SMILES
CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=CC(=C(C=C3)OCC4=CC=CC=N4)Cl)C#N)NC(=O)/C=C/CN(C)C
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+
InChIKey
JWNPDZNEKVCWMY-VQHVLOKHSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=9915743"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 557 Topological Polar Surface Area 112
XlogP 4.9 Complexity 881
Heavy Atom Count 40 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Full List of Drug Formulations (DFMs) Containing This API
          Neratinib 40 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Mannitol; Ferric oxide red; Talc; Titanium dioxide; Water; Crospovidone; Povidone; Silicon dioxide; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified
                   Dosage Form Oral Tablet
                   Company Puma Biotechnology
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Neratinib Maleate 40 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Colloidal Silicon Dioxide; Mannitol; Microcrystalline Cellulose; Crospovidone; Povidone; Magnesium Stearate; Purified Water; Polyvinyl Alcohol; Titanium Dioxide; Polyethylene Glycol; Talc; Iron Oxide Red
                   Dosage Form Tablet
                   Company Puma Biotechnology
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
References
1 FDA label for approved neratinib from the official website of the U.S. Food and Drug Administration.
2 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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