ID: ALA3706535

PubChem CID: 122197285

Max Phase: Preclinical

Molecular Formula: C26H18ClFN4O3

Molecular Weight: 488.91

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES: O=NCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1

Standard InChI: InChI=1S/C26H18ClFN4O3/c27-22-12-19(5-8-25(22)34-14-16-2-1-3-18(28)10-16)32-26-21-11-17(4-7-23(21)29-15-30-26)24-9-6-20(35-24)13-31-33/h1-12,15H,13-14H2,(H,29,30,32)

Standard InChI Key: GZUMUKHYSKSWHS-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   10.8864  -14.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6138  -15.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7549  -15.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9801  -15.1571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1843  -15.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3118  -14.9004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4569  -15.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222  -16.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6434  -16.1647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4742  -15.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7961  -16.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9310  -16.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0686  -16.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8570  -14.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5549  -13.6912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2822  -14.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3707  -16.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8255  -17.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5571  -17.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4274  -14.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1254  -13.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1276  -17.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4982  -16.0627    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.4003  -17.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5867  -18.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0162  -18.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7394  -18.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3140  -18.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2095  -16.4707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4414  -18.4343    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6493  -15.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0749  -20.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7688  -19.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3435  -19.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3892  -16.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  7  1  0
  4  3  1  0
  5  1  1  0
  6  2  1  0
  7  5  2  0
  8  3  2  0
  9  2  1  0
 10  4  1  0
 11 13  2  0
 12  8  1  0
 13 17  1  0
 14  1  1  0
 15 14  2  0
 16 15  1  0
 17  9  1  0
 18 22  2  0
 19 18  1  0
 20 21  2  0
 21 14  1  0
 22 24  1  0
 23 11  1  0
 24 17  2  0
 25 19  1  0
 26 28  1  0
 27 26  2  0
 28 25  1  0
 29 31  1  0
 30 27  1  0
 31 10  1  0
 32 34  1  0
 33 32  2  0
 34 28  2  0
  6 16  2  0
 20  7  1  0
 10 12  2  0
 18 11  1  0
 33 27  1  0
 29 35  2  0
M  END

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Small molecule	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 488.91	Molecular Weight (Monoisotopic): 488.1051	AlogP: 7.27	#Rotatable Bonds: 8
Polar Surface Area: 89.61	Molecular Species: NEUTRAL	HBA: 7	HBD: 1
#RO5 Violations: 1	HBA (Lipinski): 7	HBD (Lipinski): 1	#RO5 Violations (Lipinski): 1
CX Acidic pKa: ┄	CX Basic pKa: 3.83	CX LogP: 6.11	CX LogD: 6.11
Aromatic Rings: 5	Heavy Atoms: 35	QED Weighted: 0.23	Np Likeness Score: -1.42

References

1. Takakusa H, Wahlin MD, Zhao C, Hanson KL, New LS, Chan EC, Nelson SD.. (2011) Metabolic intermediate complex formation of human cytochrome P450 3A4 by lapatinib., 39 (6): [PMID:21363997] [10.1124/dmd.110.037531]
2. Hardy KD, Wahlin MD, Papageorgiou I, Unadkat JD, Rettie AE, Nelson SD.. (2013) Studies on the role of metabolic activation in tyrosine kinase inhibitor-dependent hepatotoxicity: induction of CYP3A4 enhances the cytotoxicity of lapatinib in HepaRG cells., 42 [PMID:24191259] [10.1124/dmd.113.054817]
3. Chan EC, New LS, Chua TB, Yap CW, Ho HK, Nelson SD.. (2012) Interaction of lapatinib with cytochrome P450 3A5., 40 (7): [PMID:22511346] [10.1124/dmd.112.044958]
4. Barbara JE, Kazmi F, Parkinson A, Buckley DB.. (2013) Metabolism-dependent inhibition of CYP3A4 by lapatinib: evidence for formation of a metabolic intermediate complex with a nitroso/oxime metabolite formed via a nitrone intermediate., 41 (5): [PMID:23404373] [10.1124/dmd.113.051151]
5. Castellino S, O'Mara M, Koch K, Borts DJ, Bowers GD, MacLauchlin C.. (2012) Human metabolism of lapatinib, a dual kinase inhibitor: implications for hepatotoxicity., 40 (1): [PMID:21965624] [10.1124/dmd.111.040949]

Names and Identifiers

Alternative Forms

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source