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    Chemistry

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    Also known as: 755037-03-7, Bay 73-4506, Stivarga, 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)-n-methylpicolinamide, Regorafenibum, Regorafenib (bay 73-4506)
    Molecular Formula
    C21H15ClF4N4O3
    Molecular Weight
    482.8  g/mol
    InChI Key
    FNHKPVJBJVTLMP-UHFFFAOYSA-N
    FDA UNII
    24T2A1DOYB
    Regorafenib
    Regorafenib is the anhydrous form of regorafenib, an orally bioavailable small molecule with potential antiangiogenic and antineoplastic activities. Regorafenib binds to and inhibits vascular endothelial growth factor receptors (VEGFRs) 2 and 3, and Ret, Kit, PDGFR and Raf kinases, which may result in the inhibition of tumor angiogenesis and tumor cell proliferation. VEGFRs are receptor tyrosine kinases that play important roles in tumor angiogenesis; the receptor tyrosine kinases RET, KIT, and PDGFR, and the serine/threonine-specific Raf kinase are involved in tumor cell signaling.
    Regorafenib is a Kinase Inhibitor. The mechanism of action of regorafenib is as a Protein Kinase Inhibitor, and Cytochrome P450 2C9 Inhibitor.
    1 2D Structure

    Regorafenib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C21H15ClF4N4O3/c1-27-19(31)18-10-13(6-7-28-18)33-12-3-5-17(16(23)9-12)30-20(32)29-11-2-4-15(22)14(8-11)21(24,25)26/h2-10H,1H3,(H,27,31)(H2,29,30,32)
    2.1.3 InChI Key
    FNHKPVJBJVTLMP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CNC(=O)C1=NC=CC(=C1)OC2=CC(=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F)F
    2.2 Other Identifiers
    2.2.1 UNII
    24T2A1DOYB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(4-(((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl)amino)-3-fluorophenoxy)-n-methylpyridine-2-carboxamide

    2. Bay 73-4506

    3. Bay-73-4506

    4. Bay73-4506

    5. Stivarga

    2.3.2 Depositor-Supplied Synonyms

    1. 755037-03-7

    2. Bay 73-4506

    3. Stivarga

    4. 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)-n-methylpicolinamide

    5. Regorafenibum

    6. Regorafenib (bay 73-4506)

    7. Bay73-4506

    8. Bay-73-4506

    9. 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-n-methylpyridine-2-carboxamide

    10. Regorafenib-13c-d3

    11. 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-3-fluorophenoxy]-n-methylpyridine-2-carboxamide

    12. 24t2a1doyb

    13. Chembl1946170

    14. Chebi:68647

    15. Bay-734506

    16. Stivarga (tn)

    17. 4-(4-(((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl)amino)-3-fluorophenoxy)-n-methylpyridine-2-carboxamide

    18. Regorafenib [inn]

    19. Regorafenib [usan:inn]

    20. Unii-24t2a1doyb

    21. Fluoro-sorafenib

    22. 4-(4-(((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl}amino)-3-fluorophenoxy)-n-methylpyridine-2-carboxamide

    23. Regorafenib [mi]

    24. Regorafenib (usan/inn)

    25. Regorafenib [vandf]

    26. Regorafenib Anhydrous

    27. Regorafenib [who-dd]

    28. Mls006010303

    29. Regorafenib Crystalline Form I

    30. Schembl432230

    31. Regorafenib,bay 73-4506

    32. Gtpl5891

    33. Dtxsid60226441

    34. Ex-a058

    35. Regorafenib - Bay 73-4506

    36. Bcpp000352

    37. Hms3654k16

    38. Hms3672e15

    39. Bcp02105

    40. Bkd17855

    41. Zinc6745272

    42. Bdbm50363397

    43. Mfcd16038047

    44. Nsc763932

    45. Nsc800865

    46. S1178

    47. Akos015951107

    48. Am81251

    49. Bay 734506

    50. Bcp9000384

    51. Ccg-269571

    52. Cs-0170

    53. Db08896

    54. Nsc-763932

    55. Nsc-800865

    56. Sb16819

    57. Ncgc00263138-01

    58. Ncgc00263138-13

    59. Ncgc00263138-19

    60. 2-pyridinecarboxamide,4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-n-methyl-

    61. 835621-08-4

    62. Ac-25075

    63. Ac-31116

    64. As-16304

    65. Hy-10331

    66. Smr004701370

    67. Ft-0674338

    68. R0142

    69. Sw218097-2

    70. Cas:835621-07-3;regorafenib Hydrochloride

    71. Regorafenib (bay73-4506,fluoro-sorafenib)

    72. A25020

    73. D10138

    74. Ab01565826_02

    75. Sr-01000941571

    76. Q3891664

    77. Sr-01000941571-1

    78. Brd-k16730910-001-02-4

    79. 2-pyridinecarboxamide, 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-n-methyl-

    80. 4-[4-({[4-chloro-3-(trifluoromethy)phenyl]carbamoyl}amino)-3-fluorophenoxy]-1-methylpyridine-2-carboxamide

    81. 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic Acid Methylamide

    82. Regorafenib;1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenyl)urea

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 482.8 g/mol
    Molecular Formula C21H15ClF4N4O3
    XLogP34.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass482.0768807 g/mol
    Monoisotopic Mass482.0768807 g/mol
    Topological Polar Surface Area92.4 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity686
    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 Information
    1 of 2  
    Drug NameStivarga
    PubMed HealthRegorafenib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelStivarga (regorafenib) has the chemical name 4-[4-({[4-chloro-3-(trifluoromethyl) phenyl] carbamoyl} amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide monohydrate. Regorafenib has the following structural formula:Regorafenib is a monohydrate and...
    Active IngredientRegorafenib
    Dosage FormTablet
    Routeoral; Oral
    Strength40mg
    Market StatusPrescription
    CompanyBayer Healthcare Pharms; Bayer Hlthcare

    2 of 2  
    Drug NameStivarga
    PubMed HealthRegorafenib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelStivarga (regorafenib) has the chemical name 4-[4-({[4-chloro-3-(trifluoromethyl) phenyl] carbamoyl} amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide monohydrate. Regorafenib has the following structural formula:Regorafenib is a monohydrate and...
    Active IngredientRegorafenib
    Dosage FormTablet
    Routeoral; Oral
    Strength40mg
    Market StatusPrescription
    CompanyBayer Healthcare Pharms; Bayer Hlthcare

    4.2 Drug Indication

    Regorafenib is indicated for the treatment of patients with metastatic colorectal cancer (CRC) who have been previously treated with fluoropyrimidine-, oxaliplatin- and irinotecan-based chemotherapy, an anti-VEGF therapy, and, if KRAS wild type, an anti-EGFR therapy. Regorafenib is also indicated for the treatment of patients with locally advanced, unresectable or metastatic gastrointestinal stromal tumour (GIST) who have been previously treated with imatinib mesylate and sunitinib malate. Regorafenib is also indicated for the treatment of patients with hepatocellular carcinoma (HCC) previously treated with sorafenib.

    FDA Label

    Stivarga is indicated as monotherapy for the treatment of adult patients with:

    - metastatic colorectal cancer (CRC) who have been previously treated with, or are not considered candidates for, available therapies - these include fluoropyrimidine-based chemotherapy, an anti-VEGF therapy and an anti-EGFR therapy;

    - unresectable or metastatic gastrointestinal stromal tumors (GIST) who progressed on or are intolerant to prior treatment with imatinib and sunitinib;

    - hepatocellular carcinoma (HCC) who have been previously treated with sorafenib.

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    REGORAFENIB
    5.1.2 FDA UNII
    24T2A1DOYB
    5.1.3 Pharmacological Classes
    Kinase Inhibitor [EPC]; Protein Kinase Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]
    5.2 ATC Code

    L01EX05

    L01XE21

    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

    L01EX - Other protein kinase inhibitors

    L01EX05 - Regorafenib

    5.3 Absorption, Distribution and Excretion

    Absorption

    Cmax = 2.5 g/mL; Tmax = 4 hours; AUC = 70.4 g*h/mL; Cmax, steady-state = 3.9 g/mL; AUC, steady-state = 58.3 g*h/mL; The mean relative bioavailability of tablets compared to an oral solution is 69% to 83%.

    Route of Elimination

    Approximately 71% of a radiolabeled dose was excreted in feces (47% as parent compound, 24% as metabolites) and 19% of the dose was excreted in urine (17% as glucuronides) within 12 days after administration of a radiolabeled oral solution at a dose of 120 mg.

    Volume of Distribution

    Regorafenib undergoes enterohepatic circulation with multiple plasma concentration peaks observed across the 24-hour dosing interval.

    5.4 Metabolism/Metabolites

    Regorafenib is metabolized by CYP3A4 and UGT1A9. The main circulating metabolites of regorafenib measured at steady-state in human plasma are M-2 (N-oxide) and M-5 (N-oxide and N-desmethyl), both of them having similar in vitro pharmacological activity and steady-state concentrations as regorafenib. M-2 and M-5 are highly protein bound (99.8% and 99.95%, respectively). Regorafenib is an inhibitor of P-glycoprotein, while its active metabolites M-2 (N-oxide) and M-5 (N-oxide and N-desmethyl) are substrates of P-glycoprotein.

    5.5 Biological Half-Life

    Regorafenib, 160 mg oral dose = 28 hours (14 - 58 hours); M2 metabolite, 160 mg oral dose = 25 hours (14-32 hours); M5 metabolite, 160 mg oral dose = 51 hours (32-72 hours);

    5.6 Mechanism of Action

    Regorafenib is a small molecule inhibitor of multiple membrane-bound and intracellular kinases involved in normal cellular functions and in pathologic processes such as oncogenesis, tumor angiogenesis, and maintenance of the tumor microenvironment. In in vitro biochemical or cellular assays, regorafenib or its major human active metabolites M-2 and M-5 inhibited the activity of RET, VEGFR1, VEGFR2, VEGFR3, KIT, PDGFR-alpha, PDGFR-beta, FGFR1, FGFR2, TIE2, DDR2, TrkA, Eph2A, RAF-1, BRAF, BRAFV600E , SAPK2, PTK5, and Abl at concentrations of regorafenib that have been achieved clinically. In in vivo models, regorafenib demonstrated anti-angiogenic activity in a rat tumor model, and inhibition of tumor growth as well as anti-metastatic activity in several mouse xenograft models including some for human colorectal carcinoma.

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    ABOUT THIS PAGE

    Regorafenib Monohydrate Manufacturers

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

    Regorafenib Monohydrate Suppliers

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

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

    Regorafenib Monohydrate USDMF

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

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

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

    Regorafenib Monohydrate KDMF

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

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

    After submitting a Regorafenib Monohydrate 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 Regorafenib Monohydrate API can apply through the Korea Drug Master File (KDMF).

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

    Regorafenib Monohydrate WC

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

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

    Regorafenib Monohydrate 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 Regorafenib Monohydrate as an active pharmaceutical ingredient (API).

    Finished drug products

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

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

    Regorafenib Monohydrate GMP

    Regorafenib Monohydrate 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 Regorafenib Monohydrate 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 Regorafenib Monohydrate GMP manufacturer or Regorafenib Monohydrate GMP API supplier for your needs.

    Regorafenib Monohydrate CoA

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

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

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