List of Korea Drug Master Files (KDMF) for Gefitinib Active Pharmaceutical Ingredient submitted to the Review Authority in Korea and listed on PharmaCompass.com

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13 CEP/COS
5 JDMF
10 EU WC
10 KDMF
9 NDC API
33 Listed Suppliers
$ API Reference Price

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7 Intermediates Suppliers

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31 FDF Dossiers
6 FDA Orange Book
6 Europe
5 Canada
2 Australia
1 South Africa
11 Listed Dossiers

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4 Finished Drug Prices
9 Annual Reports

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Synopsis

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Europe

Canada

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0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

6,625,714

Annual Reports (USD Million)

3,166

Finished Drug Prices

165 RELATED EXCIPIENT COMPANIES

278EXCIPIENTS BY APPLICATIONS

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

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 Formula	C₂₂H₂₄ClFN₄O₃
Molecular Weight	446.9 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	8
Exact Mass	446.1520965 g/mol
Monoisotopic Mass	446.1520965 g/mol
Topological Polar Surface Area	68.7 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	545
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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

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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