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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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    22-Mar-2022
    26-May-2025
    KGS
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    ABOUT THIS PAGE

    Looking for 184475-35-2 / Gefitinib API manufacturers, exporters & distributors?

    Gefitinib manufacturers, exporters & distributors 1

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    PharmaCompass offers a list of Gefitinib API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Gefitinib manufacturer or Gefitinib supplier for your needs.

    Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Gefitinib manufacturer or Gefitinib supplier.

    PharmaCompass also assists you with knowing the Gefitinib API Price utilized in the formulation of products. Gefitinib API Price is not always fixed or binding as the Gefitinib Price is obtained through a variety of data sources. The Gefitinib Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

    API | Excipient name

    Gefitinib

    Synonyms

    184475-35-2, Iressa, Zd1839, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine, Irressat, Zd 1839

    Cas Number

    184475-35-2

    Unique Ingredient Identifier (UNII)

    S65743JHBS

    About 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.

    IRE Manufacturers

    A IRE manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of IRE, including repackagers and relabelers. The FDA regulates IRE manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. IRE API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of IRE manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    IRE Suppliers

    A IRE supplier is an individual or a company that provides IRE active pharmaceutical ingredient (API) or IRE finished formulations upon request. The IRE suppliers may include IRE API manufacturers, exporters, distributors and traders.

    click here to find a list of IRE suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    IRE USDMF

    A IRE DMF (Drug Master File) is a document detailing the whole manufacturing process of IRE active pharmaceutical ingredient (API) in detail. Different forms of IRE DMFs exist exist since differing nations have different regulations, such as IRE USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A IRE DMF submitted to regulatory agencies in the US is known as a USDMF. IRE USDMF includes data on IRE's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The IRE USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of IRE suppliers with USDMF on PharmaCompass.

    IRE JDMF

    The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

    The IRE Drug Master File in Japan (IRE JDMF) empowers IRE API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

    PMDA reviews the IRE JDMF during the approval evaluation for pharmaceutical products. At the time of IRE JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

    click here to find a list of IRE suppliers with JDMF on PharmaCompass.

    IRE KDMF

    In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

    Pharmaceutical companies submit a IRE Drug Master File in Korea (IRE KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of IRE. The MFDS reviews the IRE KDMF as part of the drug registration process and uses the information provided in the IRE KDMF to evaluate the safety and efficacy of the drug.

    After submitting a IRE KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their IRE API can apply through the Korea Drug Master File (KDMF).

    click here to find a list of IRE suppliers with KDMF on PharmaCompass.

    IRE CEP

    A IRE CEP of the European Pharmacopoeia monograph is often referred to as a IRE Certificate of Suitability (COS). The purpose of a IRE CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of IRE EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of IRE to their clients by showing that a IRE CEP has been issued for it. The manufacturer submits a IRE CEP (COS) as part of the market authorization procedure, and it takes on the role of a IRE CEP holder for the record. Additionally, the data presented in the IRE CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the IRE DMF.

    A IRE CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. IRE CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

    click here to find a list of IRE suppliers with CEP (COS) on PharmaCompass.

    IRE WC

    A IRE written confirmation (IRE WC) is an official document issued by a regulatory agency to a IRE manufacturer, verifying that the manufacturing facility of a IRE active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting IRE APIs or IRE finished pharmaceutical products to another nation, regulatory agencies frequently require a IRE WC (written confirmation) as part of the regulatory process.

    click here to find a list of IRE suppliers with Written Confirmation (WC) on PharmaCompass.

    IRE NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing IRE as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for IRE API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture IRE as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain IRE and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a IRE NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of IRE suppliers with NDC on PharmaCompass.

    IRE GMP

    IRE Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of IRE GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right IRE GMP manufacturer or IRE GMP API supplier for your needs.

    IRE CoA

    A IRE CoA (Certificate of Analysis) is a formal document that attests to IRE's compliance with IRE specifications and serves as a tool for batch-level quality control.

    IRE CoA mostly includes findings from lab analyses of a specific batch. For each IRE CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    IRE may be tested according to a variety of international standards, such as European Pharmacopoeia (IRE EP), IRE JP (Japanese Pharmacopeia) and the US Pharmacopoeia (IRE USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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