TIRBANIBULIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H29N3O3
Molecular Weight	431.5268
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(CC1=NC=C(C=C1)C2=CC=C(OCCN3CCOCC3)C=C2)NCC4=CC=CC=C4

InChI

InChIKey=HUNGUWOZPQBXGX-UHFFFAOYSA-N

InChI=1S/C26H29N3O3/c30-26(28-19-21-4-2-1-3-5-21)18-24-9-6-23(20-27-24)22-7-10-25(11-8-22)32-17-14-29-12-15-31-16-13-29/h1-11,20H,12-19H2,(H,28,30)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23314737 | https://www.ncbi.nlm.nih.gov/pubmed/27737538

KX-01 is a dual inhibitor of Src kinase and tubulin polymerization. KX01 promotes the induction of p53, G2/M arrest of proliferating cell populations and subsequent apoptosis via the stimulation of Caspase-3 and PARP cleavage. The drug was developed by Kinex Pharmaceuticals and reached phase II of clinical trials for the treatment of Castration-Resistant Prostate Cancer and Actinic Keratosis. KX-01 demonstrated good in vitro pofile against different cancer cell lines with IC50 in nanomolar range.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein kinase SRC 19 Target ID: CHEMBL267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23314737 \| https://www.ncbi.nlm.nih.gov/pubmed/27737538	Inhibitor 8297
tubulin complex assembly 1 Target ID: GO:0007021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23314737 \| https://www.ncbi.nlm.nih.gov/pubmed/27737538	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Castrate-resistant prostate cancer 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23314737	Primary		Phase II 1132	Unknown Approved Use Unknown
Actinic keratosis 11 Sources: https://clinicaltrials.gov/ct2/show/NCT02838628	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Expression of Src and FAK in hepatocellular carcinoma and the effect of Src inhibitors on hepatocellular carcinoma in vitro.	2009 Jul	18979199
Synthesis and pharmacological evaluation of thieno[2,3-b]pyridine derivatives as novel c-Src inhibitors.	2011 Apr 15	21459579
Thiazolyl N-benzyl-substituted acetamide derivatives: synthesis, Src kinase inhibitory and anticancer activities.	2011 Oct	21852023
KX-01, a novel Src kinase inhibitor directed toward the peptide substrate site, synergizes with tamoxifen in estrogen receptor α positive breast cancer.	2012 Apr	21509526
A phase I trial of KX2-391, a novel non-ATP competitive substrate-pocket- directed SRC inhibitor, in patients with advanced malignancies.	2013 Aug	23361621

Patents

Sample Use Guides

In Vivo Use Guide

Patients recieve 40 mg of oral KX-01 twice-daily. Ointment form should be applied once daily.

Route of Administration: Other

In Vitro Use Guide

PC3-LN4 human prostate cancer cells were treated with 10(-4)-10(4) nM of KX-01 for 72 hours and GI50 value was determined to be 40 nM.

Name

Type

Language

TIRBANIBULIN

Official Name

English

KX2391

Code

English

KX-2-391

Code

English

KLISYRI

Brand Name

English

TIRBANIBULIN [ORANGE BOOK]

Common Name

English

Tirbanibulin [WHO-DD]

Common Name

English

2-PYRIDINEACETAMIDE, 5-(4-(2-(4-MORPHOLINYL)ETHOXY)PHENYL)-N-(PHENYLMETHYL)-

Systematic Name

English

N-BENZYL-2-(5-(4-(2-MORPHOLIN-4-YLETHOXY)PHENYL)PYRIDIN-2-YL)ACETAMIDE

Systematic Name

English

KX01

Code

English

tirbanibulin [INN]

Common Name

English

KX-01

Code

English

TIRBANIBULIN [USAN]

Common Name

English

KX-2391

Code

English

KX2-391

Code

English

Code System Code Type Description

FDA UNII

4V9848RS5G