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Chemistry

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Also known as: 1123837-84-2, Mgcd516, Mg-516, Mgcd-516, Sitravatinib [inn], Cwg62q1vtb

Molecular Formula

C₃₃H₂₉F₂N₅O₄S

Molecular Weight

629.7 g/mol

InChI Key

WLAVZAAODLTUSW-UHFFFAOYSA-N

FDA UNII

CWG62Q1VTB

Sitravatinib is an orally bioavailable, receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Upon administration, sitravatinib binds to and inhibits the activity of several RTKs including hepatocyte growth factor receptor (HGFR; c-Met; MET), tyrosine-protein kinase receptor UFO (AXL receptor tyrosine kinase; AXL), mast/stem cell growth factor receptor (SCFR; c-kit; KIT), the receptor tyrosine kinase MER, discoidin domain receptor 2 (DDR2), vascular endothelial growth factor receptor (VEGFR) types 1 (VEGFR-1; FLT1), 2 (VEGFR-2; KDR; Flk-1) and 3 (VEGFR-3), members of the platelet-derived growth factor receptor (PDGFR) family, RET (rearranged during transfection), tropomyosin-related kinases (TRK) and members of the ephrin (Eph) family of receptor tyrosine kinases. This may result in both the inhibition of signal transduction pathways mediated by these RTKs and the reduction of tumor cell proliferation in cancer cell types that overexpress these RTKs.

1 2D Structure

Sitravatinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-N'-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

2.1.2 InChI

InChI=1S/C33H29F2N5O4S/c1-43-15-14-36-18-20-2-8-25(38-19-20)29-17-26-30(45-29)28(10-13-37-26)44-27-9-7-23(16-24(27)35)40-32(42)33(11-12-33)31(41)39-22-5-3-21(34)4-6-22/h2-10,13,16-17,19,36H,11-12,14-15,18H2,1H3,(H,39,41)(H,40,42)

2.1.3 InChI Key

WLAVZAAODLTUSW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COCCNCC1=CN=C(C=C1)C2=CC3=NC=CC(=C3S2)OC4=C(C=C(C=C4)NC(=O)C5(CC5)C(=O)NC6=CC=C(C=C6)F)F

2.2 Other Identifiers

2.2.1 UNII

CWG62Q1VTB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mgcd516

2.3.2 Depositor-Supplied Synonyms

1. 1123837-84-2

2. Mgcd516

3. Mg-516

4. Mgcd-516

5. Sitravatinib [inn]

6. Cwg62q1vtb

7. Sitravatinib (mgcd516)

8. Mg-91516

9. Mg516

10. 1-n'-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

11. N-(3-fluoro-4-((2-(5-(((2-methoxyethyl)amino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)phenyl)-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

12. 1,1-cyclopropanedicarboxamide, N-(3-fluoro-4-((2-(5-(((2-methoxyethyl)amino)methyl)-2-pyridinyl)thieno(3,2-b)pyridin-7-yl)oxy)phenyl)-n'-(4-fluorophenyl)-

13. 1,1-cyclopropanedicarboxamide, N-[3-fluoro-4-[[2-[5-[[(2-methoxyethyl)amino]methyl]-2-pyridinyl]thieno[3,2-b]pyridin-7-yl]oxy]phenyl]-n'-(4- Fluorophenyl)-

14. N-(3-fluoro-4-((2-(5-(((2-methoxyethyl)amino)methyl)pyridin-2-yl)thieno(3,2-b)pyridin-7-yl)oxy)phenyl)-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

15. Unii-cwg62q1vtb

16. Sitravatinib (usan/inn)

17. Sitravatinib [usan:inn]

18. Sitravatinib [usan]

19. Schembl172015

20. Sitravatinib [who-dd]

21. Gcd516

22. Gtpl9920

23. Chembl3989926

24. Mgcd516;mg516

25. Gcd-516

26. Dtxsid801100124

27. Bcp29099

28. Ex-a2588

29. Bdbm50467574

30. Nsc788203

31. S8573

32. Zinc164334830

33. Ccg-270287

34. Cs-5652

35. Db15036

36. Nsc-788203

37. Sb17195

38. Ncgc00483926-01

39. Ac-36164

40. Bs-14332

41. Bs166446

42. Hy-16961

43. D11140

44. D83649

45. A910305

46. Q27275860

47. Mgcd516;mgcd-516;mgcd 516;mg516;mg 516;mg-516

48. 1609655-67-5

2.4 Create Date

2009-04-13

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₂₉F₂N₅O₄S
Molecular Weight	629.7 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	629.19083192 g/mol
Monoisotopic Mass	629.19083192 g/mol
Topological Polar Surface Area	143 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	1000
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