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    Chemistry

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    Also known as: 183319-69-9, Erlotinib hcl, Tarceva, Osi-774, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine hydrochloride, Osi 774
    Molecular Formula
    C22H24ClN3O4
    Molecular Weight
    429.9  g/mol
    InChI Key
    GTTBEUCJPZQMDZ-UHFFFAOYSA-N
    FDA UNII
    DA87705X9K
    Erlotinib Hydrochloride
    A quinazoline derivative and ANTINEOPLASTIC AGENT that functions as a PROTEIN KINASE INHIBITOR for EGFR associated tyrosine kinase. It is used in the treatment of NON-SMALL CELL LUNG CANCER.
    1 2D Structure

    Erlotinib Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;hydrochloride
    2.1.2 InChI
    InChI=1S/C22H23N3O4.ClH/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22;/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25);1H
    2.1.3 InChI Key
    GTTBEUCJPZQMDZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    DA87705X9K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 11c Erlotinib

    2. 11c-erlotinib

    3. 358,774, Cp

    4. 358774, Cp

    5. Cp 358,774

    6. Cp 358774

    7. Cp-358,774

    8. Cp-358774

    9. Cp358,774

    10. Cp358774

    11. Erlotinib

    12. Erlotinib Hcl

    13. Hcl, Erlotinib

    14. Hydrochloride, Erlotinib

    15. N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

    16. Osi 774

    17. Osi-774

    18. Osi774

    19. Tarceva

    2.3.2 Depositor-Supplied Synonyms

    1. 183319-69-9

    2. Erlotinib Hcl

    3. Tarceva

    4. Osi-774

    5. N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine Hydrochloride

    6. Osi 774

    7. Erlotinib (hydrochloride)

    8. Cp-358774

    9. Cp 358774

    10. Erlotinib, Hydrochloride Salt

    11. Tarceva (erlotinib Hydrochloride)

    12. Nsc 718781

    13. Cp-358,774-01

    14. Da87705x9k

    15. 6,7-bis(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline Hydrochloride

    16. N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;hydrochloride

    17. Cp-358

    18. 4-quinazolinamine, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-, Hydrochloride (1:1)

    19. Nsc-718781

    20. 6,7-bis(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline Hcl

    21. 183319-69-9 (hcl)

    22. 4-(m-ethynylanilino)-6,7-bis(2-methoxyethoxy)quinazoline Monohydrochloride

    23. Cp-358774-01

    24. 4-quinazolinamine, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-, Monohydrochloride

    25. [6,7-bis-(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)-amine Hydrochloride

    26. N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine Monohydrochloride.

    27. Chebi:53509

    28. Osi-744

    29. Smr002529980

    30. Erlotinib Hydrochloride [usan]

    31. Nsc718781

    32. 183319-69-9 Pound Not183321-74-6

    33. Erlotinib Hcl (osi-744)

    34. Unii-da87705x9k

    35. Erlotinib, Hcl

    36. Erlotinib Hcl Salt

    37. Erlotinib Hydrochloride [usan:inn]

    38. Tarceva (osi)

    39. Tarceva Hydrochloride

    40. Mfcd07781272

    41. Erlotonib Hydrochloride

    42. Erlotinib Hydrochlroide

    43. Erlotinib(osi-744)

    44. Mls003899192

    45. Mls004774139

    46. Chembl1079742

    47. Nsc 718781) Hcl

    48. Dtxsid10171412

    49. Ex-a064

    50. Erlotinib Hydrochloride (tarceva)

    51. Bcpp000238

    52. Bcp02600

    53. Erlotinib Hydrochloride [mi]

    54. Ac-400

    55. Erlotinib Hydrochloride [jan]

    56. S1023

    57. Akos015849087

    58. Bcp9000658

    59. Ccg-269002

    60. Cs-0123

    61. Erlotinib Hydrochloride [mart.]

    62. Ks-1202

    63. Pb30965

    64. Sb16917

    65. Erlotinib Hydrochloride [usp-rs]

    66. Erlotinib Hydrochloride [who-dd]

    67. Ro-50-8231

    68. Be164421

    69. Bp-30224

    70. Hy-12008

    71. (cp358774

    72. Db-011534

    73. Am20090622

    74. Erlotinib Hydrochloride [orange Book]

    75. Ft-0651479

    76. Ec-000.2313

    77. E-4007

    78. 319e699

    79. Q27124083

    80. F0001-2385

    81. Erlotinib Hydrochloride Is Known As A Egfr Kinase Inhibitor.

    82. Erlotinib Hydrochloride,cp-358774, Osi-774, Nsc 718781

    83. 6,7-bis-(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline Hydrochloride

    84. [6,7-bis(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl- Phenyl)amine Hydrochloride

    85. N-(3-ethenylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine Hydrochloride

    86. N-(3-ethynylphenyl)-6,7-bis(1-methoxyethoxy)-4-quinazolinamine Hydrochloride

    87. N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine, Monohydrochloride

    88. N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-quinazolin-4-amine Hydrochloride

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 429.9 g/mol
    Molecular Formula C22H24ClN3O4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count11
    Exact Mass429.1455339 g/mol
    Monoisotopic Mass429.1455339 g/mol
    Topological Polar Surface Area74.7 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity525
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameErlotinib hydrochloride
    Drug LabelTARCEVA (erlotinib), a kinase inhibitor, is a quinazolinamine with the chemical name N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine. TARCEVA contains erlotinib as the hydrochloride salt that has the following structural formula:Erloti...
    Active IngredientErlotinib hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 150mg base; eq 25mg base
    Market StatusPrescription
    CompanyMylan Pharms

    2 of 4  
    Drug NameTarceva
    PubMed HealthErlotinib (By mouth)
    Drug ClassesAntineoplastic Agent, Immunological Agent
    Drug LabelTARCEVA (erlotinib), a kinase inhibitor, is a quinazolinamine with the chemical name N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine. TARCEVA contains erlotinib as the hydrochloride salt that has the following structural formula:Erloti...
    Active IngredientErlotinib hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 150mg base; eq 25mg base
    Market StatusPrescription
    CompanyOsi Pharms

    3 of 4  
    Drug NameErlotinib hydrochloride
    Drug LabelTARCEVA (erlotinib), a kinase inhibitor, is a quinazolinamine with the chemical name N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine. TARCEVA contains erlotinib as the hydrochloride salt that has the following structural formula:Erloti...
    Active IngredientErlotinib hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 150mg base; eq 25mg base
    Market StatusPrescription
    CompanyMylan Pharms

    4 of 4  
    Drug NameTarceva
    PubMed HealthErlotinib (By mouth)
    Drug ClassesAntineoplastic Agent, Immunological Agent
    Drug LabelTARCEVA (erlotinib), a kinase inhibitor, is a quinazolinamine with the chemical name N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine. TARCEVA contains erlotinib as the hydrochloride salt that has the following structural formula:Erloti...
    Active IngredientErlotinib hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 150mg base; eq 25mg base
    Market StatusPrescription
    CompanyOsi Pharms

    4.2 Drug Indication

    * Non-small cell lung cancer (NSCLC):

    Tarceva is also indicated for switch maintenance treatment in patients with locally advanced or metastatic non-small cell lung cancer with EGFR activating mutations and stable disease after first-line chemotherapy.

    Tarceva is also indicated for the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of at least one prior chemotherapy regimen.

    In patients with tumours without EGFR activating mutations, Tarceva is indicated when other treatment options are not considered suitable.

    When prescribing Tarceva, factors associated with prolonged survival should be taken into account.

    No survival benefit or other clinically relevant effects of the treatment have been demonstrated in patients with Epidermal Growth Factor Receptor (EGFR)-IHC - negative tumours.

    * Pancreatic cancer :

    Tarceva in combination with gemcitabine is indicated for the treatment of patients with metastatic pancreatic cancer .

    When prescribing Tarceva, factors associated with prolonged survival should be taken into account.

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Protein Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
    5.3 ATC Code

    L01EB02

    API Reference Price

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    08-Apr-2021
    04-Mar-2024
    KGS
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    Average Price (USD/KGS)

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - EQ 100MG BASE **Federa...DOSAGE - TABLET;ORAL - EQ 100MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21743

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    DOSAGE - TABLET;ORAL - EQ 150MG BASE **Federa...DOSAGE - TABLET;ORAL - EQ 150MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21743

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    DOSAGE - TABLET;ORAL - EQ 25MG BASE **Federal...DOSAGE - TABLET;ORAL - EQ 25MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21743

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