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Chemistry

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Also known as: Bal101553, Bal-101553, Lisavanbulin [inn], Lisavanbulin [usan], 1263384-43-5, 5pt0qp06x5

Molecular Formula

C₂₆H₂₉N₉O₃

Molecular Weight

515.6 g/mol

InChI Key

NIPZLALJRAHABJ-IBGZPJMESA-N

FDA UNII

5PT0QP06X5

Lisavanbulin is an orally available, highly water-soluble lysine prodrug of the synthetic small molecule BAL27862 with potential antitumor activity. Upon administration of lisavanbulin and conversion into the active form BAL27862, this agent binds to tubulin at a site distinct from the vinca-alkaloid-binding site, and prevents tubulin polymerization and destabilizes microtubules, ultimately leading to cell cycle arrest, blockage of cell division and an induction of cell death in cancer cells.

1 2D Structure

Lisavanbulin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2,6-diamino-N-[4-[2-[2-[4-(2-cyanoethylamino)-1,2,5-oxadiazol-3-yl]benzimidazol-1-yl]acetyl]phenyl]hexanamide

2.1.2 InChI

InChI=1S/C26H29N9O3/c27-13-4-3-6-19(29)26(37)31-18-11-9-17(10-12-18)22(36)16-35-21-8-2-1-7-20(21)32-25(35)23-24(34-38-33-23)30-15-5-14-28/h1-2,7-12,19H,3-6,13,15-16,27,29H2,(H,30,34)(H,31,37)/t19-/m0/s1

2.1.3 InChI Key

NIPZLALJRAHABJ-IBGZPJMESA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)N=C(N2CC(=O)C3=CC=C(C=C3)NC(=O)C(CCCCN)N)C4=NON=C4NCCC#N

2.1.5 Isomeric SMILES

C1=CC=C2C(=C1)N=C(N2CC(=O)C3=CC=C(C=C3)NC(=O)[C@H](CCCCN)N)C4=NON=C4NCCC#N

2.2 Other Identifiers

2.2.1 UNII

5PT0QP06X5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2s)-2,6-diamino-n-(4-(2-(2-(4-((2-cyanoethyl)amino)-1,2,5-oxadiazol-3-yl)-1h-benzimidazol-1-yl)acetyl)phenyl)hexanamide

2. Bal101553

2.3.2 Depositor-Supplied Synonyms

1. Bal101553

2. Bal-101553

3. Lisavanbulin [inn]

4. Lisavanbulin [usan]

5. 1263384-43-5

6. 5pt0qp06x5

7. Microtubule-targeted Agent Bal101553

8. (2s)-2,6-diamino-n-(4-(2-(2-(4-((2-cyanoethyl)amino)-1,2,5-oxadiazol-3-yl)-1h-benzimidazol-1-yl)acetyl)phenyl)hexanamide

9. Hexanamide, 2,6-diamino-n-(4-(2-(2-(4-((2-cyanoethyl)amino)-1,2,5-oxadiazol-3-yl)-1h-benzimidazol-1-yl)acetyl)phenyl)-, (2s)-

10. Lisavanbulin (usan/inn)

11. Lisavanbulin [usan:inn]

12. Unii-5pt0qp06x5

13. Lisavanbulin [who-dd]

14. Schembl1160313

15. Chembl4297595

16. Glxc-25728

17. Ex-a4306

18. Nsc764608

19. Nsc789724

20. Who 10401

21. Bal 101553

22. Db15224

23. Nsc-764608

24. Nsc-789724

25. D11494

26. Q27262705

2.4 Create Date

2010-05-03

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₉N₉O₃
Molecular Weight	515.6 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	13
Exact Mass	515.23933582 g/mol
Monoisotopic Mass	515.23933582 g/mol
Topological Polar Surface Area	191 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	828
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Immune Checkpoint Inhibitors

Drugs that block negative regulator IMMUNE CHECKPOINT proteins (e.g., PD-1 RECEPTOR and CTLA-4 ANTIGEN) thereby increasing suppressed immune activation in immunotherapies. (See all compounds classified as Immune Checkpoint Inhibitors.)

Drugs in Development