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Details

Stereochemistry ACHIRAL
Molecular Formula C25H22N6.ClH
Molecular Weight 442.943
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LDN-193189 MONOHYDROCHLORIDE

SMILES

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

InChI

InChIKey=PCCDKTWDGDFRME-UHFFFAOYSA-N
InChI=1S/C25H22N6.ClH/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;1H

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P36894
Gene ID: 657.0
Gene Symbol: BMPR1A
Target Organism: Homo sapiens (Human)
30.0 nM [IC50]
Target ID: Q04771
Gene ID: 90.0
Gene Symbol: ACVR1
Target Organism: Homo sapiens (Human)
5.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
BMP type I receptor inhibition reduces heterotopic [corrected] ossification.
2008 Dec
Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism.
2008 Jan
BMP9 is a proliferative and survival factor for human hepatocellular carcinoma cells.
2013
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: conditional caALK2-transgenic mice with Ad.Cre
3 mg/kg LDN-193189 was used once or twice daily
Route of Administration: Intraperitoneal
0.1 uM final concentration in stem cell differentiation conditions
Name Type Language
LDN-193189 MONOHYDROCHLORIDE
Common Name English
4-(6-(4-(PIPERAZIN-1-YL)PHENYL-PYRAZOLO(1,5-A)PYRIMIDIN-3-YL)QUINOLINE HYDROCHLORIDE
Systematic Name English
QUINOLINE, 4-(6-(4-(1-PIPERAZINYL)PHENYL)PYRAZOLO(1,5-A)PYRIMIDIN-3-YL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 393513
Created by admin on Sat Dec 16 10:54:48 GMT 2023 , Edited by admin on Sat Dec 16 10:54:48 GMT 2023
Code System Code Type Description
PUBCHEM
54613581
Created by admin on Sat Dec 16 10:54:48 GMT 2023 , Edited by admin on Sat Dec 16 10:54:48 GMT 2023
PRIMARY
FDA UNII
PLH51K438W
Created by admin on Sat Dec 16 10:54:48 GMT 2023 , Edited by admin on Sat Dec 16 10:54:48 GMT 2023
PRIMARY
CAS
1062368-62-0
Created by admin on Sat Dec 16 10:54:48 GMT 2023 , Edited by admin on Sat Dec 16 10:54:48 GMT 2023
PRIMARY