NP-MRD: Showing NP-Card for Gefitinib (NP0136934)

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Record Information

Version

2.0

Created at

2022-05-30 16:28:53 UTC

Updated at

2022-05-30 16:28:53 UTC

NP-MRD ID

NP0136934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gefitinib

Description

Gefitinib, also known as iressa or ZD 1839, belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups. This leads to inappropriate activation of the anti-apoptotic Ras signalling cascade, eventually leading to uncontrolled cell proliferation. Gefitinib is a drug which is used for the continued treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of either platinum-based or docetaxel chemotherapies. Adverse drug reactions (ADRs) are acceptable for a potentially fatal disease. Gefitinib is a very strong basic compound (based on its pKa). In humans, gefitinib is involved in gefitinib action pathway. IPASS (IRESSA Pan-Asia Study) was a randomized, large-scale, double-blinded study which compared gefitinib vs. Gefitinib was first documented in 2004 (PMID: 15284455). Carboplatin/ paclitaxel as a first-line treatment in advanced NSCLC.IPASS studied 1,217 patients with confirmed adenocarcinoma histology who were former or never smokers (PMID: 15329413) (PMID: 14981586) (PMID: 15068398) (PMID: 20573926).

Structure

MOL 3D MOL SDF PDB SMILES InChI

317
  Mrv0541 02231214352D          

 31 34  0  0  0  0            999 V2000
   10.2087   -2.9100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.6471   -2.1016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8084   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.8303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5181   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    1.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5085   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2372   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2182   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9469   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9374   -1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 31  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5 20  1  0  0  0  0
  5 26  1  0  0  0  0
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  8 21  1  0  0  0  0
  8 25  2  0  0  0  0
  9 23  2  0  0  0  0
  9 25  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
 18 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
 24 27  2  0  0  0  0
 24 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.5347   -5.3870    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7090   -4.0005    0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4070   -3.1608    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -3.6768    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0492   -2.5421   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1410    3.0757   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4368    3.7417   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3970    4.7075   -0.3718 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8150    2.4353   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5535   -1.4836    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.9736    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738   -1.8151    0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979   -1.3127    0.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431    0.0823    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    0.4796    0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6009    0.0425   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9431    0.4159    0.1959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8704    0.0135   -0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3149    1.2740   -1.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2777    2.1882   -1.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0819    0.0817    0.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0524    0.0805    1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538    1.6003    1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    0.5134   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156   -1.0671   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7726   -0.4063   -0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4343   -0.7346   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0911    1.7508   -0.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6187    3.6246   -0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5490    1.9899    1.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2395    1.8556    0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3 21  2  0
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 21 20  1  0
 20 19  2  0
 19  9  1  0
  9 10  1  0
 10 11  1  0
 11 18  2  0
 18 16  1  0
 16 17  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 12  2  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
 31 26  1  0
  5 19  1  0
 12 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 23 42  1  0
 23 43  1  0
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 27 48  1  0
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 30 53  1  0
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 20 41  1  0
 10 37  1  0
 18 40  1  0
 13 39  1  0
 12 38  1  0
  7 36  1  0
  4 35  1  0
M  END

317
  Mrv0541 02231214352D          

 31 34  0  0  0  0            999 V2000
   10.2087   -2.9100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.6471   -2.1016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8084   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.8303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5181   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2372   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2182   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9469   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9374   -1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 31  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5 20  1  0  0  0  0
  5 26  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 21  1  0  0  0  0
  8 25  2  0  0  0  0
  9 23  2  0  0  0  0
  9 25  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
 18 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
 24 27  2  0  0  0  0
 24 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

> <INCHI_KEY>
XGALLCVXEZPNRQ-UHFFFAOYSA-N

> <FORMULA>
C22H24ClFN4O3

> <MOLECULAR_WEIGHT>
446.902

> <EXACT_MASS>
446.152096566

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
46.1136503263008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.750953734666667

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.10506416809685

> <JCHEM_PKA_STRONGEST_BASIC>
6.846602821831034

> <JCHEM_POLAR_SURFACE_AREA>
68.74000000000001

> <JCHEM_REFRACTIVITY>
117.50680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gefitinib

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 317                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      19.056  -5.432   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0      21.741  -3.923   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       3.080  -0.728   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   0.812   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.082   3.892   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.748   0.812   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      16.442  -0.781   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      16.460   3.945   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      17.855   1.550   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.081   1.582   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   1.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -0.728   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   0.812   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   0.812   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -1.498   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   1.582   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   1.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.083   1.582   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750   0.812   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   3.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.083   3.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750   3.892   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.460   0.758   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.767  -1.567   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.855   3.154   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082   5.432   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.749  -3.107   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.109  -0.812   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.074  -3.892   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.434  -1.598   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.416  -3.137   0.000  0.00  0.00           C+0
CONECT    1   29                                                            
CONECT    2   31                                                            
CONECT    3   14   15                                                       
CONECT    4   16   17                                                       
CONECT    5   20   26                                                       
CONECT    6   10   11   12                                                  
CONECT    7   23   24                                                       
CONECT    8   21   25                                                       
CONECT    9   23   25                                                       
CONECT   10    6   13                                                       
CONECT   11    6   14                                                       
CONECT   12    6   15                                                       
CONECT   13   10   16                                                       
CONECT   14    3   11                                                       
CONECT   15    3   12                                                       
CONECT   16    4   13                                                       
CONECT   17    4   19   20                                                  
CONECT   18   19   21   23                                                  
CONECT   19   17   18                                                       
CONECT   20    5   17   22                                                  
CONECT   21    8   18   22                                                  
CONECT   22   20   21                                                       
CONECT   23    7    9   18                                                  
CONECT   24    7   27   28                                                  
CONECT   25    8    9                                                       
CONECT   26    5                                                            
CONECT   27   24   29                                                       
CONECT   28   24   30                                                       
CONECT   29    1   27   31                                                  
CONECT   30   28   31                                                       
CONECT   31    2   29   30                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
4-(3'-Chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline	ChEBI
Gefitinibum	ChEBI
Iressa	ChEBI
Irressat	ChEBI
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamine	ChEBI
ZD 1839	ChEBI
ZD-1839	ChEBI
ZD1839	ChEBI
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamide	HMDB

Chemical Formula

C₂₂H₂₄ClFN₄O₃

Average Mass

446.9020 Da

Monoisotopic Mass

446.15210 Da

IUPAC Name

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine

Traditional Name

gefitinib

CAS Registry Number

Not Available

SMILES

COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1

InChI Identifier

InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

InChI Key

XGALLCVXEZPNRQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolinamines

Alternative Parents

Substituents

Quinazolinamine
Anisole
Aniline or substituted anilines
Alkyl aryl ether
Aminopyrimidine
Chlorobenzene
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Morpholine
Oxazinane
Pyrimidine
Benzenoid
Imidolactam
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Secondary amine
Azacycle
Dialkyl ether
Ether
Oxacycle
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organofluoride
Organochloride
Organopnictogen compound
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinazolines (CHEBI:49668 )
morpholines (CHEBI:49668 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.02	ALOGPS
logP	3.75	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	16.11	ChemAxon
pKa (Strongest Basic)	6.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	117.51 m³·mol⁻¹	ChemAxon
Polarizability	46.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0014462

DrugBank ID

DB00317

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

110217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gefitinib

METLIN ID

Not Available

PubChem Compound

123631

PDB ID

Not Available

ChEBI ID

49668

Good Scents ID

Not Available

References

General References

Sordella R, Bell DW, Haber DA, Settleman J: Gefitinib-sensitizing EGFR mutations in lung cancer activate anti-apoptotic pathways. Science. 2004 Aug 20;305(5687):1163-7. doi: 10.1126/science.1101637. Epub 2004 Jul 29. [PubMed:15284455 ]
Pao W, Miller V, Zakowski M, Doherty J, Politi K, Sarkaria I, Singh B, Heelan R, Rusch V, Fulton L, Mardis E, Kupfer D, Wilson R, Kris M, Varmus H: EGF receptor gene mutations are common in lung cancers from "never smokers" and are associated with sensitivity of tumors to gefitinib and erlotinib. Proc Natl Acad Sci U S A. 2004 Sep 7;101(36):13306-11. doi: 10.1073/pnas.0405220101. Epub 2004 Aug 25. [PubMed:15329413 ]
Kelly K, Averbuch S: Gefitinib: phase II and III results in advanced non-small cell lung cancer. Semin Oncol. 2004 Feb;31(1 Suppl 1):93-9. doi: 10.1053/j.seminoncol.2003.12.020. [PubMed:14981586 ]
Ranson M, Wardell S: Gefitinib, a novel, orally administered agent for the treatment of cancer. J Clin Pharm Ther. 2004 Apr;29(2):95-103. doi: 10.1111/j.1365-2710.2004.00543.x. [PubMed:15068398 ]
Maemondo M, Inoue A, Kobayashi K, Sugawara S, Oizumi S, Isobe H, Gemma A, Harada M, Yoshizawa H, Kinoshita I, Fujita Y, Okinaga S, Hirano H, Yoshimori K, Harada T, Ogura T, Ando M, Miyazawa H, Tanaka T, Saijo Y, Hagiwara K, Morita S, Nukiwa T: Gefitinib or chemotherapy for non-small-cell lung cancer with mutated EGFR. N Engl J Med. 2010 Jun 24;362(25):2380-8. doi: 10.1056/NEJMoa0909530. [PubMed:20573926 ]

Showing NP-Card for Gefitinib (NP0136934)

MOL for NP0136934 (Gefitinib)

3D MOL for NP0136934 (Gefitinib)

3D SDF for NP0136934 (Gefitinib)

3D-SDF for NP0136934 (Gefitinib)

PDB for NP0136934 (Gefitinib)

3D PDB for NP0136934 (Gefitinib)

SMILES for NP0136934 (Gefitinib)

INCHI for NP0136934 (Gefitinib)

Structure for NP0136934 (Gefitinib)

3D Structure for NP0136934 (Gefitinib)