4-(4-Methyl-piperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

ID: ALA941

Cas Number: 152459-95-5

PubChem CID: 5291

Product Number: I124963, Order Now?

Max Phase: Approved

First Approval: 2001

Molecular Formula: C29H31N7O

Molecular Weight: 493.62

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Glamox | Gleevec | Imatinib | NSC-743414 | NSC-759854 | STI-571 | Imatinib|152459-95-5|STI571|Imatinib (STI571)|sti-571|Imatinib free base|Glamox|N-(4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide|Cgp 57148|STI 571|CCRIS 9076|UNII-BKJ8M8G5HI|BKJ8M8G5HI|Imatinib (INN)|NSC-743414|NSC-759854|4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE|CHEBI:45783|CGP-57148|152459-95-5 (free base)|CHEMBL9Show More⌵

Synonyms from Alternative Forms(15): Imatinib mesylate | Imatinib mesilate | Imatinib methanesulfonate | Gleevec | Imatinib (as mesilate) | Imatinib accord | Imatinib medac | Imatinib methane sulfonate | Qti571 | NSC-716051 | QTI-571 | STI 571 | STI-571 | STI571 | Glivec

Canonical SMILES:  Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Nc1nccc(-c2cccnc2)n1

Standard InChI:  InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)

Standard InChI Key:  KTUFNOKKBVMGRW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
    6.9208   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -2.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -2.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -2.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -2.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -3.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -3.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3458   -1.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1583   -3.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5458   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9750   -1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -2.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  5  1  0
  5  1  1  0
  6 13  1  0
  7  2  2  0
  8 18  1  0
  9  4  1  0
 10 25  1  0
 11  1  2  0
 12  3  1  0
 13  9  2  0
 14  7  1  0
 15  4  2  0
 16  3  2  0
 17 32  2  0
 18 28  1  0
 19 12  2  0
 20 12  1  0
 21 15  1  0
 22  8  1  0
 23  8  1  0
 24 22  1  0
 25 23  1  0
 26  7  1  0
 27 11  1  0
 28 31  1  0
 29 21  2  0
 30 19  1  0
 31 20  2  0
 32 14  1  0
 33 10  1  0
 34 14  2  0
 35 37  2  0
 36 15  1  0
 37 34  1  0
 27 26  2  0
 29 13  1  0
 17 35  1  0
 28 30  2  0
 24 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA941

   Imatinib (STI571)

2. Alternative Forms:

   

   ALA941

   Imatinib Mesylate (STI571)
3. 

   ALA941

   Imatinib-d3

Molecule Features

Natural Product: Yes

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: 493.62

Molecular Weight (Monoisotopic): 493.2590

AlogP: 4.59

#Rotatable Bonds: 7

Polar Surface Area: 86.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: 7.84

CX LogP: 4.38

CX LogD: 3.80

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.39

Np Likeness Score: -1.80

References

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Source

Source(18):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• Clinical Candidates
• DrugMatrix
• TP-search Transporter Database
• AstraZeneca Deposited Data
• Curated Drug Metabolism Pathways
• BindingDB Database
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• Kuster lab chemical proteomics drug profiling
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset
• Zimmerman Lab Biotransformation data Dec 2023