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    Chemistry

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    Also known as: 877399-52-5, Xalkori, Pf-02341066, (r)-crizotinib, Pf-2341066, Pf 2341066
    Molecular Formula
    C21H22Cl2FN5O
    Molecular Weight
    450.3  g/mol
    InChI Key
    KTEIFNKAUNYNJU-GFCCVEGCSA-N
    FDA UNII
    53AH36668S
    Crizotinib
    A piperidine and aminopyridine derivative that acts as an inhibitor of RECEPTOR PROTEIN-TYROSINE KINASES, including ANAPLASTIC LYMPHOMA KINASE (ALK) and HEPATOCYTE GROWTH FACTOR RECEPTOR (HGFR; c-Met). It is used in the treatment of NON-SMALL CELL LUNG CANCER.
    Crizotinib is a Kinase Inhibitor. The mechanism of action of crizotinib is as a Cytochrome P450 3A Inhibitor, and Receptor Tyrosine Kinase Inhibitor, and Cytochrome P450 2B6 Inhibitor, and P-Glycoprotein Inhibitor, and Organic Cation Transporter 1 Inhibitor, and Organic Cation Transporter 2 Inhibitor.
    1 2D Structure

    Crizotinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine
    2.1.2 InChI
    InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
    2.1.3 InChI Key
    KTEIFNKAUNYNJU-GFCCVEGCSA-N
    2.1.4 Canonical SMILES
    CC(C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
    2.1.5 Isomeric SMILES
    C[C@H](C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
    2.2 Other Identifiers
    2.2.1 UNII
    53AH36668S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Pf 02341066

    2. Pf 2341066

    3. Pf-02341066

    4. Pf-2341066

    5. Pf02341066

    6. Pf2341066

    7. Xalkori

    2.3.2 Depositor-Supplied Synonyms

    1. 877399-52-5

    2. Xalkori

    3. Pf-02341066

    4. (r)-crizotinib

    5. Pf-2341066

    6. Pf 2341066

    7. Crizotinib (pf-02341066)

    8. (r)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-amine

    9. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1h-pyrazol-4-yl]-2-pyridinamine

    10. Pf 02341066

    11. Pf2341066

    12. Chembl601719

    13. Crizotinib (pf-2341066)

    14. Chebi:64310

    15. 877399-52-5 (free Base)

    16. 53ah36668s

    17. Nsc-756645

    18. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1h-pyrazol-4-yl]pyridin-2-amine

    19. 2-pyridinamine, 3-((1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(4-piperidinyl)-1h-pyrazol-4-yl)-

    20. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)pyridin-2-amine

    21. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine

    22. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1h-pyrazol-4-yl]pyridin-2-amine

    23. (r)-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)-pyridin-2-ylamine

    24. Xalkori (tn)

    25. Crizotinib [usan]

    26. Crizotinib [usan:inn]

    27. Crizotinibum

    28. Unii-53ah36668s

    29. 3-((1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-amine

    30. Vgh

    31. Crizotinib- Bio-x

    32. Crizotinib [mi]

    33. Crizotinib [inn]

    34. Crizotinib [jan]

    35. Pf02341066

    36. Crizotinib [vandf]

    37. Crizotinib [mart.]

    38. Crizotinib [who-dd]

    39. Schembl93829

    40. Pf-2341066,crizotinib

    41. Crizotinib (jan/usan/inn)

    42. Gtpl4903

    43. Crizotinib [orange Book]

    44. Crizotinib, >=98% (hplc)

    45. Pf-2341066 - Crizotinib

    46. Ex-a096

    47. Bcpp000116

    48. Dtxsid701009329

    49. Amy10313

    50. Bdbm50306682

    51. Mfcd12407409

    52. Nsc749005

    53. Nsc749769

    54. Nsc800080

    55. Zinc35902489

    56. Akos015901233

    57. Akos015995207

    58. Ccg-264803

    59. Db08865

    60. Gs-6178

    61. Nsc 756645

    62. Nsc-749005

    63. Nsc-749769

    64. Nsc-800080

    65. Ncgc00250400-01

    66. Ncgc00250400-02

    67. Ncgc00250400-09

    68. Ncgc00250400-12

    69. Bc164334

    70. Hy-50878

    71. Bb 0261738

    72. Sw202555-3

    73. D09731

    74. 399p525

    75. J-510370

    76. Q5186964

    77. Brd-k78431006-001-01-1

    78. Brd-k78431006-001-03-7

    79. 877399-52-5, 877399-53-6 (acetate)

    80. 3-(2,6-dichloro-3-fluorobenzyloxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-amine

    81. (r)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-am Ine

    82. 3-(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy-5-1-(4-piperidinyl)-1h-pyrazol-4-yl-2-pyridinamine

    83. 3-[(r)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)-pyridin-2-ylamine

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 450.3 g/mol
    Molecular Formula C21H22Cl2FN5O
    XLogP33.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass449.1185439 g/mol
    Monoisotopic Mass449.1185439 g/mol
    Topological Polar Surface Area78 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity558
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameXalkori
    PubMed HealthCrizotinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelXALKORI (crizotinib) is an oral receptor tyrosine kinase inhibitor. The molecular formula for crizotinib is C21H22Cl2FN5O. The molecular weight is 450.34 Daltons. Crizotinib is described chemically as (R)-3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[...
    Active IngredientCrizotinib
    Dosage FormCapsule
    RouteOral
    Strength200mg; 250mg
    Market StatusPrescription
    CompanyPf Prism Cv

    2 of 2  
    Drug NameXalkori
    PubMed HealthCrizotinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelXALKORI (crizotinib) is an oral receptor tyrosine kinase inhibitor. The molecular formula for crizotinib is C21H22Cl2FN5O. The molecular weight is 450.34 Daltons. Crizotinib is described chemically as (R)-3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[...
    Active IngredientCrizotinib
    Dosage FormCapsule
    RouteOral
    Strength200mg; 250mg
    Market StatusPrescription
    CompanyPf Prism Cv

    4.2 Drug Indication

    Crizotinib is used for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) that is anaplastic-lymphoma kinase (ALK)-positive as detected by a FDA-approved test.

    FDA Label

    Xalkori is indicated for the first-line treatment of adults with anaplastic lymphoma kinase (ALK) positive advanced non-small cell lung cancer (NSCLC).

    Xalkori is indicated for the treatment of adults with previously treated anaplastic lymphoma kinase (ALK) positive advanced non-small cell lung cancer (NSCLC).

    Treatment of lung malignant neoplasms

    Treatment of anaplastic large cell lymphoma, Treatment of inflammatory myofibroblastic tumours

    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 Active Moiety
    CRIZOTINIB
    5.2.2 FDA UNII
    53AH36668S
    5.2.3 Pharmacological Classes
    Cytochrome P450 3A Inhibitors [MoA]; Kinase Inhibitor [EPC]; Organic Cation Transporter 1 Inhibitors [MoA]; Organic Cation Transporter 2 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Receptor Tyrosine Kinase Inhibitors [MoA]; Cytochrome P450 2B6 Inhibitors [MoA]
    5.3 ATC Code

    L01ED01

    L01XE16

    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

    L01ED - Anaplastic lymphoma kinase (alk) inhibitors

    L01ED01 - Crizotinib

    5.4 Absorption, Distribution and Excretion

    Absorption

    The peak serum concentration was reached in 4 to 6 hours following an oral single-dose administration. Steady state was reached within 15 days when a dose of 250 mg twice daily was administered. The mean absolute bioavailability was 43% (range of 32% to 66%) following a single 250 mg oral dose. When taken with high-fat meal, AUC and Cmax were reduced.

    Route of Elimination

    Following the administration of a single 250 mg radiolabeled crizotinib dose to healthy subjects, 63% and 22% of the administered dose was recovered in feces and urine, respectively. Unchanged crizotinib represented approximately 53% and 2.3% of the administered dose in feces and urine, respectively.

    Volume of Distribution

    Mean volume of distribution (Vss) is 1772 L following intravenous administration of a 50 mg dose. This high volume of distribution suggest extensive distribution into tissue from plasma.

    Clearance

    The mean apparent clearance (CL/F) of crizotinib was lower at steady state (60 L/hr) after 250 mg twice daily than that after a single 250 mg oral dose (100 L/hr), which was likely due to autoinhibition of CYP3A by crizotinib after multiple dosing.

    5.5 Metabolism/Metabolites

    Crizotinib is metabolized by CYP3A4 and CYP3A5 in which these enzymes mediates the O-dealkylation of the drug.

    5.6 Biological Half-Life

    Plasma terminal half-life, patients = 42 hours

    5.7 Mechanism of Action

    Crizotinib is a tyrosine kinase receptor inhibitor. More specifically, it inhibits anaplastic lymphoma kinase (ALK), hepatocyte growth factor receptor (HGFR, c-MET), and Recepteur d'Origine Nantais (RON). Abnormalities in the ALK gene caused by mutations or translocations may lead to expression of oncogenic fusion proteins. In patients with NSCLC, they have the EML4-ALK gene. Crizotinib inhibits ALK tyrosine kinase which ultimately results in decreased proliferation of cells that carry the genetic mutation and tumour survivability.

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    ABOUT THIS PAGE

    Crizotinib Manufacturers

    A Crizotinib manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Crizotinib, including repackagers and relabelers. The FDA regulates Crizotinib manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Crizotinib 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 Crizotinib manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Crizotinib Suppliers

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

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

    Crizotinib USDMF

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

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

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

    Crizotinib WC

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

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

    Crizotinib 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 Crizotinib as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Crizotinib 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 Crizotinib 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 Crizotinib and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Crizotinib NDC to their finished compounded human drug products, they may choose to do so.

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

    Crizotinib GMP

    Crizotinib 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 Crizotinib 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 Crizotinib GMP manufacturer or Crizotinib GMP API supplier for your needs.

    Crizotinib CoA

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

    Crizotinib CoA mostly includes findings from lab analyses of a specific batch. For each Crizotinib 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.

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