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Also known as: 1013920-15-4, Vorolanib [inn], Yp8g3i74el, Cm082, N-[(3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide, X-82

Molecular Formula

C₂₃H₂₆FN₅O₃

Molecular Weight

439.5 g/mol

InChI Key

KMIOJWCYOHBUJS-HAKPAVFJSA-N

FDA UNII

YP8G3I74EL

Vorolanib is an orally available small molecule dual inhibitor targeting human vascular endothelial growth factor receptors (VEGFRs) and platelet-derived growth factor receptors (PDGFRs) with antiangiogenic and antineoplastic activities. Vorolanib inhibits all isoforms of VEGFR and PDGFR, which may result in the inhibition of tumor angiogenesis and tumor cell proliferation, and the induction of tumor cell death. Both VEGFRs and PDGFRs are receptor tyrosine kinases that may be upregulated in various tumor cell types. Vorolanib has been shown to reduce tissue toxicity by 95 percent compared with first-generation kinase inhibitors.

1 2D Structure

Vorolanib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(3S)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

2.1.2 InChI

InChI=1S/C23H26FN5O3/c1-12-19(10-17-16-9-14(24)5-6-18(16)27-21(17)30)25-13(2)20(12)22(31)26-15-7-8-29(11-15)23(32)28(3)4/h5-6,9-10,15,25H,7-8,11H2,1-4H3,(H,26,31)(H,27,30)/b17-10-/t15-/m0/s1

2.1.3 InChI Key

KMIOJWCYOHBUJS-HAKPAVFJSA-N

2.1.4 Canonical SMILES

CC1=C(NC(=C1C(=O)NC2CCN(C2)C(=O)N(C)C)C)C=C3C4=C(C=CC(=C4)F)NC3=O

2.1.5 Isomeric SMILES

CC1=C(NC(=C1C(=O)N[C@H]2CCN(C2)C(=O)N(C)C)C)/C=C\3/C4=C(C=CC(=C4)F)NC3=O

2.2 Other Identifiers

2.2.1 UNII

YP8G3I74EL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cm082

2. N-((3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl)-5-((z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

2.3.2 Depositor-Supplied Synonyms

1. 1013920-15-4

2. Vorolanib [inn]

3. Yp8g3i74el

4. Cm082

5. N-[(3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide

6. X-82

7. (s,z)-n-(1-(dimethylcarbamoyl)pyrrolidin-3-yl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

8. 1h-pyrrole-3-carboxamide, N-((3s)-1-((dimethylamino)carbonyl)-3-pyrrolidinyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-

9. N-((3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl)-5-((z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

10. Unii-yp8g3i74el

11. Vorolanib [who-dd]

12. Schembl2439528

13. Chembl4297587

14. Gtpl11618

15. Eyp-1901

16. Cm-082

17. S6843

18. Db15247

19. Example 8 [wo2008033562a2]

20. Ac-35712

21. Hy-109019

22. Cs-0030517

23. X-082

24. Q27294638

2.4 Create Date

2012-08-20

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₆FN₅O₃
Molecular Weight	439.5 g/mol
XLogP3	1.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	439.20196787 g/mol
Monoisotopic Mass	439.20196787 g/mol
Topological Polar Surface Area	97.5 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	803
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

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