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Also known as: Veru-111, 1332881-26-1, 37l1jx37j5, (2-(1h-indol-3-yl)-1h-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone, [2-(1h-indol-3-yl)-1h-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone, [2-(1h-indol-3-yl)-1h-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone

Molecular Formula

C₂₁H₁₉N₃O₄

Molecular Weight

377.4 g/mol

InChI Key

WQGVHOVEXMOLOK-UHFFFAOYSA-N

FDA UNII

37L1JX37J5

Sabizabulin is an orally bioavailable, small molecule tubulin inhibitor, with potential antineoplastic, antiviral and anti-inflammatory activities. Upon oral administration, sabizabulin binds to the colchicine-binding site of alpha- and beta-tubulin subunits of microtubules and crosslinks the microtubules, thereby inhibiting microtubule polymerization in tumor blood vessel endothelial cells and tumor cells. This blocks the formation of the mitotic spindle and leads to cell cycle arrest at the G2/M phase. As a result, this agent disrupts the tumor vasculature, tumor blood flow, deprives tumor cells of nutrients, and induces apoptosis. In addition, as microtubules plays an important role in intracellular transport, the inhibition of its polymerization may disrupt the transport of the androgen receptor (AR) into the cell nucleus, as well as virus trafficking around the cell. This may decrease viral replication and assembly. Inhibition of tubulin polymerization may also inhibit the release of pro-inflammatory cytokines and disrupt inflammatory cell activities. Sabizabulin is not a substrate of P-glycoprotein (Pgp), an efflux pump that when overexpressed, may confer resistance to taxane agents.

1 2D Structure

Sabizabulin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-(1H-indol-3-yl)-1H-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone

2.1.2 InChI

InChI=1S/C21H19N3O4/c1-26-17-8-12(9-18(27-2)20(17)28-3)19(25)16-11-23-21(24-16)14-10-22-15-7-5-4-6-13(14)15/h4-11,22H,1-3H3,(H,23,24)

2.1.3 InChI Key

WQGVHOVEXMOLOK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=CC(=CC(=C1OC)OC)C(=O)C2=CN=C(N2)C3=CNC4=CC=CC=C43

2.2 Other Identifiers

2.2.1 UNII

37L1JX37J5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2-(1h-indol-3-yl)-1h-imidazol-5-yl)-(3,4,5-trimethoxyphenyl)methanone

2. Methanone, (2-(1h-indol-3-yl)-1h-imidazol-5-yl)(3,4,5-trimethoxyphenyl)-

3. Veru-111

2.3.2 Depositor-Supplied Synonyms

1. Veru-111

2. 1332881-26-1

3. 37l1jx37j5

4. (2-(1h-indol-3-yl)-1h-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

5. [2-(1h-indol-3-yl)-1h-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone

6. [2-(1h-indol-3-yl)-1h-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone

7. Methanone, (2-(1h-indol-3-yl)-1h-imidazol-5-yl)(3,4,5-trimethoxyphenyl)-

8. (2-(1h-indol-3-yl)-1h-imidazol-5-yl)(3,4,5-trimethoxyphenyl)methanone

9. Sabizabulin [inn]

10. Sabizabulin [who-dd]

11. Veru111

12. Schembl724794

13. Unii-37l1jx37j5

14. Chembl2163631

15. Schembl20850747

16. Gtpl11422

17. Abi-231

18. Hy-120599

19. Cs-0078414

20. S6772

21. Kum

2.4 Create Date

2011-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₉N₃O₄
Molecular Weight	377.4 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	377.13755610 g/mol
Monoisotopic Mass	377.13755610 g/mol
Topological Polar Surface Area	89.2 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	534
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