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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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Bone morphogenetic protein receptor type-1A
2
Target ID: P36894
Gene ID: 657.0
Gene Symbol: BMPR1A
Target Organism: Homo sapiens (Human)
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)
Inhibitor
8297
 5.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

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

Patents

20110053930
2
20120094381
2
US 20120164112 A1
2

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
In Vitro Use Guide
0.1 uM final concentration in stem cell differentiation conditions
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:54:47 UTC 2023
Edited
by admin
on Sat Dec 16 10:54:47 UTC 2023
Record UNII
PLH51K438W
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 10:54:48 UTC 2023
Code System Code Type Description
PUBCHEM
54613581
Created by admin on Sat Dec 16 10:54:48 UTC 2023 , Edited by admin on Sat Dec 16 10:54:48 UTC 2023
PRIMARY
FDA UNII
PLH51K438W
Created by admin on Sat Dec 16 10:54:48 UTC 2023 , Edited by admin on Sat Dec 16 10:54:48 UTC 2023
PRIMARY
CAS
1062368-62-0
Created by admin on Sat Dec 16 10:54:48 UTC 2023 , Edited by admin on Sat Dec 16 10:54:48 UTC 2023
PRIMARY
Related Record Type Details
Structure of LDN-193189
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of LDN-193189
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