LDN-193189

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H22N6
Molecular Weight	406.4824
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1CN(CCN1)C2=CC=C(C=C2)C3=CN4N=CC(=C4N=C3)C5=CC=NC6=CC=CC=C56

InChI

InChIKey=CDOVNWNANFFLFJ-UHFFFAOYSA-N

InChI=1S/C25H22N6/c1-2-4-24-22(3-1)21(9-10-27-24)23-16-29-31-17-19(15-28-25(23)31)18-5-7-20(8-6-18)30-13-11-26-12-14-30/h1-10,15-17,26H,11-14H2

HIDE SMILES / InChI

Molecular Formula	C25H22N6
Molecular Weight	406.4824
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=19029982
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/18621530; http://www.ncbi.nlm.nih.gov/pubmed/?term=21670081

LDN193189 is a cell-permeable, highly potent and selective BMP pathway inhibitor. It prevents Smad1, Smad5, and Smad8 phosphorylation. It is a useful tool compound to modulate stem cell differentiation (for example, neural differentiation of human ESC/iPSC in combination with SB431542). LDN-193189 blocks the production of reactive oxygen species induced by oxidized LDL during atherogenesis in human aortic endothelial cells. It was also used in animal models to treat FOP and ectopic ossification, as well as NSCLC lung cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bone morphogenetic protein receptor type-1A 2 Target ID: P36894 Gene ID: 657.0 Gene Symbol: BMPR1A Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/18621530	Inhibitor 8297		30.0 nM [IC50]
Activin receptor type-1 3 Target ID: Q04771 Gene ID: 90.0 Gene Symbol: ACVR1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/18621530	Inhibitor 8297		5.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors.	2008 Aug 1	18621530
Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism.	2008 Jan	18026094
Highly efficient neural conversion of human ES and iPS cells by dual inhibition of SMAD signaling.	2009 Mar	19252484
Dorsomorphin and LDN-193189 inhibit BMP-mediated Smad, p38 and Akt signalling in C2C12 cells.	2010 Nov	20691279
Small-molecule regulators of human stem cell self-renewal.	2011 Apr 11	21381174
BMP4 promotes prostate tumor growth in bone through osteogenesis.	2011 Aug 1	21670081
Rapid and robust generation of functional oligodendrocyte progenitor cells from epiblast stem cells.	2011 Sep 25	21946668
Inhibition of bone morphogenetic protein signaling reduces vascular calcification and atherosclerosis.	2012 Mar	22223731
BMP9 is a proliferative and survival factor for human hepatocellular carcinoma cells.	2013	23936038
ΔNp63α-mediated activation of bone morphogenetic protein signaling governs stem cell activity and plasticity in normal and malignant mammary epithelial cells.	2013 Jan 15	23243027

Patents

Sample Use Guides

In Vivo Use Guide

3 mg/kg LDN-193189 was used once or twice daily

Route of Administration: Intraperitoneal

In Vitro Use Guide

0.1 uM final concentration in stem cell differentiation conditions

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:30:57 GMT 2023` Edited by `admin` on `Sat Dec 16 10:30:57 GMT 2023`
Record UNII	W69H5YQU9O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LDN-193189

Common Name

English

QUINOLINE, 4-(6-(4-(1-PIPERAZINYL)PHENYL)PYRAZOLO(1,5-A)PYRIMIDIN-3-YL)-

Systematic Name

English

Code System Code Type Description

FDA UNII

W69H5YQU9O