LISAVANBULIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H29N9O3
Molecular Weight	515.567
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCCC[C@H](N)C(=O)NC1=CC=C(C=C1)C(=O)CN2C3=CC=CC=C3N=C2C4=NON=C4NCCC#N

InChI

InChIKey=NIPZLALJRAHABJ-IBGZPJMESA-N

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

HIDE SMILES / InChI

Molecular Formula	C26H29N9O3
Molecular Weight	515.567
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.globenewswire.com/news-release/2018/06/26/1529304/0/en/Basilea-starts-clinical-phase-2a-expansion-with-BAL101553-in-ovarian-cancer-and-glioblastoma.html | https://www.ncbi.nlm.nih.gov/pubmed/25407467

Lisavanbulin, also known as BAL-101553, a prodrug of the molecule BAL-27862 with potential antitumor activity. BAL-27862 binds to tubulin, prevents tubulin polymerization, destabilizes microtubules, arrests tumor cell proliferation, and induces cell death in cancer cells. Lisavanbulin participated in phase II clinical trials for the treatment of advanced solid tumors. Besides, the drug participates in a 1/2a clinical study in patients with recurrent glioblastoma and in patients with platinum-resistant or refractory ovarian cancer. In this study, will be characterized the safety and tolerability and to obtain efficacy data in these selected cancer types.

Originator

Approval Year

PubMed

Title	Date	PubMed
The novel microtubule-destabilizing drug BAL27862 binds to the colchicine site of tubulin with distinct effects on microtubule organization.	2014 Apr 17	24530796
Initial testing (stage 1) of BAL101553, a novel tubulin binding agent, by the pediatric preclinical testing program.	2015 Jun	25407467
The Novel Tubulin-Binding Checkpoint Activator BAL101553 Inhibits EB1-Dependent Migration and Invasion and Promotes Differentiation of Glioblastoma Stem-like Cells.	2016 Nov	27540016
The novel microtubule targeting agent BAL101553 in combination with radiotherapy in treatment-refractory tumor models.	2017 Sep	28797699

Sample Use Guides

In Vivo Use Guide

BAL101553 48-hour infusion on day 1, 8, and 15 of each 28-day cycle; oral capsule daily for one week during Cycle 2 Oral daily administration of BAL101553

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:30:52 GMT 2023` Edited by `admin` on `Sat Dec 16 11:30:52 GMT 2023`
Record UNII	5PT0QP06X5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LISAVANBULIN

Official Name

English

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)-

Systematic Name

English

LISAVANBULIN [USAN]

Common Name

English

Lisavanbulin [WHO-DD]

Common Name

English

BAL101553

Code

English

lisavanbulin [INN]

Common Name

English

(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

Systematic Name

English

MICROTUBULE-TARGETED AGENT BAL101553

Code

English

BAL-101553

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C25974