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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 of LISAVANBULIN

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
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.

Approval Year

PubMed

PubMed

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

Sample Use Guides

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
Name Type Language
LISAVANBULIN
WHO-DD  
USAN   INN  
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
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
FDA ORPHAN DRUG 828321
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
Code System Code Type Description
DRUG BANK
DB15224
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
PRIMARY
FDA UNII
5PT0QP06X5
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
PRIMARY
NCI_THESAURUS
C97664
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
PRIMARY
SMS_ID
100000174635
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
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CAS
1263384-43-5
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
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USAN
FG-141
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
PRIMARY
INN
10401
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
PRIMARY
PUBCHEM
45259014
Created by admin on Sat Dec 16 11:30:52 GMT 2023 , Edited by admin on Sat Dec 16 11:30:52 GMT 2023
PRIMARY