Dacomitinib

ID: ALA2110732

Cas Number: 1110813-31-4

PubChem CID: 11511120

Product Number: D124839, Order Now?

Max Phase: Approved

First Approval: 2018

Molecular Formula: C24H25ClFN5O2

Molecular Weight: 469.95

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dacomitinib anhydrous | Pf-00299804 | Dacomitinib|1110813-31-4|PF-00299804|PF299804|Dacomitinib (PF299804, PF299)|(E)-N-(4-((3-chloro-4-fluorophenyl)aMino)-7-Methoxyquinazolin-6-yl)-4-(piperidin-1-yl)but-2-enaMide|Dacomitinib anhydrous|(2E)-N-[4-[(3-Chloro-4-fluorophenyl)amino]-7-methoxy-6-quinazolinyl]-4-(1-piperidinyl)-2-butenamide|Dacomitinib (PF299804)|2XJX250C20|PF 00299804-03|Dacomitinib (INN)|(2e)-N-{4-[(3-Chloro-4-Fluorophenyl)amino]-7-Methoxyquinazolin-6-Yl}-4-(Piperidin-1-Yl)but-2-EnamShow More⌵

Synonyms from Alternative Forms(5): Dacomitinib | Dacomitinib hydrate | Dacomitinib monohydrate | PF-00299804-03 | Vizimpro

Canonical SMILES:  COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1NC(=O)/C=C/CN1CCCCC1

Standard InChI:  InChI=1S/C24H25ClFN5O2/c1-33-22-14-20-17(24(28-15-27-20)29-16-7-8-19(26)18(25)12-16)13-21(22)30-23(32)6-5-11-31-9-3-2-4-10-31/h5-8,12-15H,2-4,9-11H2,1H3,(H,30,32)(H,27,28,29)/b6-5+

Standard InChI Key:  LVXJQMNHJWSHET-AATRIKPKSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -4.9796    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9796    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2652    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507    0.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2652   -0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362   -0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1218    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    1.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -0.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506   -0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1651    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1651    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217    1.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795    1.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795   -0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5940    0.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5940    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795   -0.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1651   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1651   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506   -0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -0.9875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -2.6375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217    2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 15 13  1  0
 13 16  2  0
 14 15  2  0
 16 17  1  0
 14 18  1  0
 15 19  1  0
 20 18  1  0
 17 18  2  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 20 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 25 30  2  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 28 32  1  0
 19 33  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA2110732

   DACOMITINIB

2. Parent:

   

   ALA2110732

   DACOMITINIB ANHYDROUS

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 469.95

Molecular Weight (Monoisotopic): 469.1681

AlogP: 5.16

#Rotatable Bonds: 7

Polar Surface Area: 79.38

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.50

CX Basic pKa: 8.55

CX LogP: 4.71

CX LogD: 3.53

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: -1.61

References

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3. Unpublished dataset, 

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14. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

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Source

Source(11):

• Scientific Literature
• Clinical Candidates
• AstraZeneca Deposited Data
• BindingDB Database
• WHO Anatomical Therapeutic Chemical Classification
• Kuster lab chemical proteomics drug profiling
• SARS-CoV-2 Screening Data 2020-21
• EUbOPEN Chemogenomic Library
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset