LDN-193189
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MedKoo CAT#: 501105

CAS#: 1062368-24-4 (free base)

Description: LDN193189 is a highly potent small molecule BMP inhibitor with IC50 of 5 and 30 nM for ALK2 and ALK3, respectively. LDN193189 also inhibits BMP type I receptors ALK6 (TGFβ1/BMP signaling) and subsequent SMAD phosphorylation.


Price and Availability

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Price

10mg
USD 90
100mg
USD 450
1g
USD 2650
Size
Price

25mg
USD 150
200mg
USD 750
2g
USD 3850
Size
Price

50mg
USD 250
500mg
USD 1450
5g
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LDN-193189, purity > 98%, is in stock. Same day shipping after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 501105
Name: LDN-193189
CAS#: 1062368-24-4 (free base)
Chemical Formula: C25H22N6
Exact Mass: 406.19059
Molecular Weight: 406.48238
Elemental Analysis: C, 73.87; H, 5.46; N, 20.67


Related CAS #: 1062368-24-4 (free base)   1062368-62-0 (HCl)   1435934-00-1 (dihydrochloride).  

Synonym: LDN193189; LDN 193189; LDN-193189

IUPAC/Chemical Name: 4-[6-(4-Piperazin-1-yl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline

InChi Key: CDOVNWNANFFLFJ-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: C1(C2=C3N=CC(C4=CC=C(N5CCNCC5)C=C4)=CN3N=C2)=CC=NC6=CC=CC=C16


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
1062368-24-4 ( LDN-193189 free base);
1062368-62-0 ( LDN-193189 HCl)
1435934-00-1 ( LDN-193189 dihydrochloride)
  
 
 


References

1: Saeed O, Otsuka F, Polavarapu R, Karmali V, Weiss D, Davis T, Rostad B, Pachura K, Adams L, Elliott J, Taylor WR, Narula J, Kolodgie F, Virmani R, Hong CC, Finn AV. Pharmacological Suppression of Hepcidin Increases Macrophage Cholesterol Efflux and Reduces Foam Cell Formation and Atherosclerosis. Arterioscler Thromb Vasc Biol. 2011 Nov 17. [Epub ahead of print] PubMed PMID: 22095982.

2: Kudo TA, Kanetaka H, Mizuno K, Ryu Y, Miyamoto Y, Nunome S, Zhang Y, Kano M, Shimizu Y, Hayashi H. Dorsomorphin stimulates neurite outgrowth in PC12 cells via activation of a protein kinase A-dependent MEK-ERK1/2 signaling pathway. Genes Cells. 2011 Nov;16(11):1121-32. doi: 10.1111/j.1365-2443.2011.01556.x. Epub 2011 Oct 12. PubMed PMID: 21988724.

3: Vogt J, Traynor R, Sapkota GP. The specificities of small molecule inhibitors of the TGFß and BMP pathways. Cell Signal. 2011 Nov;23(11):1831-42. Epub 2011 Jun 29. PubMed PMID: 21740966.

4: Cross EE, Thomason RT, Martinez M, Hopkins CR, Hong CC, Bader DM. Application of small organic molecules reveals cooperative TGFβ and BMP regulation of mesothelial cell behaviors. ACS Chem Biol. 2011 Sep 16;6(9):952-61. Epub 2011 Jul 20. PubMed PMID: 21740033; PubMed Central PMCID: PMC3177035.

5: Theurl I, Schroll A, Sonnweber T, Nairz M, Theurl M, Willenbacher W, Eller K, Wolf D, Seifert M, Sun CC, Babitt JL, Hong CC, Menhall T, Gearing P, Lin HY, Weiss G. Pharmacologic inhibition of hepcidin expression reverses anemia of chronic inflammation in rats. Blood. 2011 Nov 3;118(18):4977-84. Epub 2011 Jul 5. PubMed PMID: 21730356; PubMed Central PMCID: PMC3208302.

6: Lee YC, Cheng CJ, Bilen MA, Lu JF, Satcher RL, Yu-Lee LY, Gallick GE, Maity SN, Lin SH. BMP4 promotes prostate tumor growth in bone through osteogenesis. Cancer Res. 2011 Aug 1;71(15):5194-203. Epub 2011 Jun 13. PubMed PMID: 21670081; PubMed Central PMCID: PMC3148283.

7: Yonezawa T, Lee JW, Hibino A, Asai M, Hojo H, Cha BY, Teruya T, Nagai K, Chung UI, Yagasaki K, Woo JT. Harmine promotes osteoblast differentiation through bone morphogenetic protein signaling. Biochem Biophys Res Commun. 2011 Jun 3;409(2):260-5. Epub 2011 May 6. PubMed PMID: 21570953.

8: Steinbicker AU, Sachidanandan C, Vonner AJ, Yusuf RZ, Deng DY, Lai CS, Rauwerdink KM, Winn JC, Saez B, Cook CM, Szekely BA, Roy CN, Seehra JS, Cuny GD, Scadden DT, Peterson RT, Bloch KD, Yu PB. Inhibition of bone morphogenetic protein signaling attenuates anemia associated with inflammation. Blood. 2011 May 5;117(18):4915-23. Epub 2011 Mar 10. PubMed PMID: 21393479; PubMed Central PMCID: PMC3100698.

9: Wang L, Trebicka E, Fu Y, Ellenbogen S, Hong CC, Babitt JL, Lin HY, Cherayil BJ. The bone morphogenetic protein-hepcidin axis as a therapeutic target in inflammatory bowel disease. Inflamm Bowel Dis. 2012 Jan;18(1):112-9. doi: 10.1002/ibd.21675. Epub 2011 Feb 23. PubMed PMID: 21351217; PubMed Central PMCID: PMC3139830.

10: Shi S, Hoogaars WM, de Gorter DJ, van Heiningen SH, Lin HY, Hong CC, Kemaladewi DU, Aartsma-Rus A, ten Dijke P, 't Hoen PA. BMP antagonists enhance myogenic differentiation and ameliorate the dystrophic phenotype in a DMD mouse model. Neurobiol Dis. 2011 Feb;41(2):353-60. Epub 2010 Oct 16. PubMed PMID: 20940052.

11: Katagiri T, Kamizono J, Nakashima Y, Kitoh H, Susami T, Haga N. [Cytokines in bone diseases. BMP signaling and fibrodysplasia ossificans progressiva]. Clin Calcium. 2010 Oct;20(10):1510-7. Review. Japanese. PubMed PMID: 20890033.

12: Cannon JE, Upton PD, Smith JC, Morrell NW. Intersegmental vessel formation in zebrafish: requirement for VEGF but not BMP signalling revealed by selective and non-selective BMP antagonists. Br J Pharmacol. 2010 Sep;161(1):140-9. PubMed PMID: 20718746; PubMed Central PMCID: PMC2962823.

13: Boergermann JH, Kopf J, Yu PB, Knaus P. Dorsomorphin and LDN-193189 inhibit BMP-mediated Smad, p38 and Akt signalling in C2C12 cells. Int J Biochem Cell Biol. 2010 Nov;42(11):1802-7. Epub 2010 Aug 5. PubMed PMID: 20691279.

14: Yu PB, Deng DY, Lai CS, Hong CC, Cuny GD, Bouxsein ML, Hong DW, McManus PM, Katagiri T, Sachidanandan C, Kamiya N, Fukuda T, Mishina Y, Peterson RT, Bloch KD. BMP type I receptor inhibition reduces heterotopic [corrected] ossification. Nat Med. 2008 Dec;14(12):1363-9. Epub 2008 Nov 30. Erratum in: Nat Med. 2009 Jan;15(1):117. PubMed PMID: 19029982; PubMed Central PMCID: PMC2846458.

15: Cuny GD, Yu PB, Laha JK, Xing X, Liu JF, Lai CS, Deng DY, Sachidanandan C, Bloch KD, Peterson RT. Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors. Bioorg Med Chem Lett. 2008 Aug 1;18(15):4388-92. Epub 2008 Jun 27. PubMed PMID: 18621530; PubMed Central PMCID: PMC2570262.