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Regorafenib

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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 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 Formula	C₂₁H₁₅ClF₄N₄O₃
Molecular Weight	482.8 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	482.0768807 g/mol
Monoisotopic Mass	482.0768807 g/mol
Topological Polar Surface Area	92.4 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	686
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 Information

1 of 2
Drug Name	Stivarga
PubMed Health	Regorafenib (By mouth)
Drug Classes	Antineoplastic Agent
Drug Label	Stivarga (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 Ingredient	Regorafenib
Dosage Form	Tablet
Route	oral; Oral
Strength	40mg
Market Status	Prescription
Company	Bayer Healthcare Pharms; Bayer Hlthcare

2 of 2
Drug Name	Stivarga
PubMed Health	Regorafenib (By mouth)
Drug Classes	Antineoplastic Agent
Drug Label	Stivarga (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 Ingredient	Regorafenib
Dosage Form	Tablet
Route	oral; Oral
Strength	40mg
Market Status	Prescription
Company	Bayer 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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