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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 of LDN-193189

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
30.0 nM [IC50]
5.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

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
Record UNII
W69H5YQU9O
Record Status Validated (UNII)
Record Version