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    Chemistry

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    Also known as: 184475-35-2, Iressa, Zd1839, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine, Irressat, Zd 1839
    Molecular Formula
    C22H24ClFN4O3
    Molecular Weight
    446.9  g/mol
    InChI Key
    XGALLCVXEZPNRQ-UHFFFAOYSA-N
    FDA UNII
    S65743JHBS
    Gefitinib
    A selective tyrosine kinase inhibitor for the EPIDERMAL GROWTH FACTOR RECEPTOR (EGFR) that is used for the treatment of locally advanced or metastatic NON-SMALL CELL LUNG CANCER.
    Gefitinib is a Kinase Inhibitor. The mechanism of action of gefitinib is as a Protein Kinase Inhibitor.
    1 2D Structure

    Gefitinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
    2.1.2 InChI
    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)
    2.1.3 InChI Key
    XGALLCVXEZPNRQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
    2.2 Other Identifiers
    2.2.1 UNII
    S65743JHBS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Iressa

    2. N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamide

    3. Zd 1839

    4. Zd1839

    2.3.2 Depositor-Supplied Synonyms

    1. 184475-35-2

    2. Iressa

    3. Zd1839

    4. N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine

    5. Irressat

    6. Zd 1839

    7. Gefitinib (zd1839)

    8. Zd-1839

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

    10. Gefitinib (gmp)

    11. N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

    12. 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline

    13. N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

    14. Mfcd04307832

    15. Chembl939

    16. Nsc-759856

    17. S65743jhbs

    18. Chebi:49668

    19. 3-chloro-4-fluoro-n-[(4z)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(1h)-ylidene]aniline

    20. N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine

    21. Gefitinib [usan]

    22. Ncgc00159455-02

    23. Dsstox_cid_21034

    24. Dsstox_rid_79614

    25. N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine

    26. Dsstox_gsid_41034

    27. 4-quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-

    28. Iressa(tm)

    29. Ire

    30. Iressa (tn)

    31. Ccris 9011

    32. Cas-184475-35-2

    33. Sr-00000000262

    34. Gefitinibum

    35. Unii-s65743jhbs

    36. Gefitinib (jan/usan/inn)

    37. Gefitinib [usan:inn:ban]

    38. Gefitini; Iressa

    39. 4-quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-

    40. N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamine

    41. Gefitinib (iressa)

    42. Gefitinib - Iressa

    43. Irressa

    44. Iressa (astrazeneca)

    45. Nchembio866-comp14

    46. Kinome_3321

    47. Kinome_3322

    48. Gefitinib [inn]

    49. Gefitinib [jan]

    50. Gefitinib [mi]

    51. Gefitinib [vandf]

    52. Gefitinib [mart.]

    53. Gefitinib [who-dd]

    54. Schembl7866

    55. Gefitinib,zd-1839,iressa

    56. Gefitinib [ema Epar]

    57. Kbioss_002241

    58. Mls003899193

    59. Cu-00000000396-1

    60. Bdbm5447

    61. Cid_123631

    62. Gtpl4941

    63. Gefitinib [orange Book]

    64. Dtxsid8041034

    65. Gefitinib [ep Monograph]

    66. Gefitinib, >=98% (hplc)

    67. Bcpp000221

    68. Hms2089b19

    69. Hms3244m21

    70. Hms3244m22

    71. Hms3244n21

    72. Hms3295a21

    73. Hms3413h08

    74. Hms3654a07

    75. Hms3677h08

    76. Hms3714a05

    77. Hms3748e17

    78. Pharmakon1600-01502274

    79. Bcp01365

    80. Tox21_111683

    81. Hy-50895g

    82. Nsc715055

    83. Nsc759856

    84. Nsc800105

    85. S1025

    86. Stk621310

    87. Zinc19632614

    88. Akos000280752

    89. Tox21_111683_1

    90. Ab20814

    91. Ac-1556

    92. Bcp9000718

    93. Ccg-220642

    94. Cs-0124

    95. Db00317

    96. Ks-1204

    97. Nsc 759856

    98. Nsc-715055

    99. Nsc-800105

    100. 4-[(3-chloro-4-fluorophenyl)amino]-7-methoxy-6-(3-morpholinopropoxy)quinazoline

    101. 4-quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-4-morpholin)propoxy)-

    102. 6-(3-morpholinopropoxy)-n-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine

    103. Ncgc00159455-03

    104. Ncgc00159455-04

    105. Ncgc00159455-05

    106. Ncgc00159455-06

    107. Ncgc00159455-08

    108. Ncgc00159455-09

    109. Ncgc00159455-14

    110. Bcb03_000781

    111. Bg164498

    112. Hy-50895

    113. Smr002204119

    114. Sy002154

    115. Am20090619

    116. Cs-0622782

    117. Ft-0602325

    118. G0546

    119. Sw199108-4

    120. Ec-000.2409

    121. D01977

    122. G-4408

    123. K00240

    124. Ab01273954-01

    125. Ab01273954-02

    126. Ab01273954-03

    127. Ab01273954_04

    128. 475g352

    129. A812870

    130. Q417824

    131. Q-201149

    132. Sr-00000000262-2

    133. Sr-00000000262-3

    134. Gefitinib, Europepharmacopoeia (ep) Reference Standard

    135. Z1551429741

    136. 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)-quinazoline

    137. Gefitinib For System Suitability, Europepharmacopoeia (ep) Reference Standard

    138. (3-chloro-4-fluoro-phenyl)-[7-methoxy-6-(3-morpholin-4-yl-propoxy)-quinazolin-4-yl]-amine

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 446.9 g/mol
    Molecular Formula C22H24ClFN4O3
    XLogP34.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count8
    Exact Mass446.1520965 g/mol
    Monoisotopic Mass446.1520965 g/mol
    Topological Polar Surface Area68.7 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity545
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    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.

    FDA Label

    Iressa is indicated for the treatment of adult patients with locally advanced or metastatic non-small-cell lung cancer with activating mutations of epidermal-growth-factor-receptor tyrosine kinase.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Gefitinib inhibits the intracellular phosphorylation of numerous tyrosine kinases associated with transmembrane cell surface receptors, including the tyrosine kinases associated with the epidermal growth factor receptor (EGFR-TK). EGFR is expressed on the cell surface of many normal cells and cancer cells.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    GEFITINIB
    5.3.2 FDA UNII
    S65743JHBS
    5.3.3 Pharmacological Classes
    Protein Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
    5.4 ATC Code

    L01XE02

    L01XE02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EB - Epidermal growth factor receptor (egfr) tyrosine kinase inhibitors

    L01EB01 - Gefitinib

    5.5 Absorption, Distribution and Excretion

    Absorption

    Absorbed slowly after oral administration with a mean bioavailability of 60%. Peak plasma levels occurs 3-7 hours post-administration. Food does not affect the bioavailability of gefitinib.

    Route of Elimination

    Elimination is by metabolism (primarily CYP3A4) and excretion in feces. Excretion is predominantly via the feces (86%), with renal elimination of drug and metabolites accounting for less than 4% of the administered dose.

    Volume of Distribution

    1400 L [IV administration]

    Clearance

    595 mL/min [IV administration]

    5.6 Metabolism/Metabolites

    Primarily hepatic via CYP3A4. Three sites of biotransformation have been identified: metabolism of the N-propoxymorpholino-group, demethylation of the methoxy-substituent on the quinazoline, and oxidative defluorination of the halogenated phenyl group.

    Gefitinib has known human metabolites that include 4-Defluoro-4-hydroxy Gefitinib and O-Desmethyl Gefitinib.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    48 hours [IV administration]

    5.8 Mechanism of Action

    Gefitinib is an inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase that binds to the adenosine triphosphate (ATP)-binding site of the enzyme. EGFR is often shown to be overexpressed in certain human carcinoma cells, such as lung and breast cancer cells. Overexpression leads to enhanced activation of the anti-apoptotic Ras signal transduction cascades, subsequently resulting in increased survival of cancer cells and uncontrolled cell proliferation. Gefitinib is the first selective inhibitor of the EGFR tyrosine kinase which is also referred to as Her1 or ErbB-1. By inhibiting EGFR tyrosine kinase, the downstream signaling cascades are also inhibited, resulting in inhibited malignant cell proliferation.

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    10-Feb-2021
    17-Oct-2024
    KGS
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