SB1578

WARNING: This product is for research use only, not for human or veterinary use.

Description:SB1578, also known as ONX-0805, is a novel, orally bioavailable JAK2 inhibitor with specificity for JAK2 within the JAK family and also potent activity against FLT3 and c-Fms. SB1578 blocks the activation of these kinases and their downstream signaling in pertinent cells, leading to inhibition of pathological cellular responses. The biochemical and cellular activities of SB1578 translate into its high efficacy in two rodent models of arthritis.

Price and Availability

SB1578 (ONX 0805) is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 205625Name: SB1578CAS#: 937273-04-6Chemical Formula: C26H30N4O4Exact Mass: 462.22671Molecular Weight: 462.54Elemental Analysis: C, 67.51; H, 6.54; N, 12.11; O, 13.84

Synonym:ONX 0805; ONX0805; ONX0805; SB1578; SB1578; SB 1578.

IUPAC/Chemical Name:(9E)-15-(2-(pyrrolidin-1-yl)ethoxy)-7,12,25-trioxa-19,21,24-triaza-tetracyclo[18.3.1.1(2,5).1(14,18)]hexacosa-1(24),2,4,9,14(26),15,17,20,22-nonaene

InChi Key:NNXDIGHYPZHXTR-ONEGZZNKSA-N

InChi Code:InChI=1S/C26H30N4O4/c1-2-12-30(11-1)13-16-33-24-7-5-21-17-20(24)18-31-14-3-4-15-32-19-22-6-8-25(34-22)23-9-10-27-26(28-21)29-23/h3-10,17H,1-2,11-16,18-19H2,(H,27,28,29)/b4-3+

SMILES Code:C1(C2=CC=C(O2)COC/C=C/COCC3=CC(N4)=CC=C3OCCN5CCCC5)=NC4=NC=C1

Technical Data

Additional Information

SB1518 (ONX 0803) has been designed to suppress the overactivity of mutant JAK2 and is currently in multiple Phase 1 studies. Data from these Phase 1 dose-ranging studies, evaluating the compound in patients with primary myelofibrosis, are anticipated in the first half of 2009.      

References

1: Madan B, Goh KC, Hart S, William AD, Jayaraman R, Ethirajulu K,Dymock BW, Wood JM. SB1578, a novel inhibitor of JAK2, FLT3, and c-Fms for thetreatment ofrheumatoid arthritis. J Immunol. 2012 Oct 15;189(8):4123-34. doi: 10.4049/jimmunol.1200675. Epub 2012 Sep 7. PubMed PMID: 22962687.

2: Poulsen A, William A, Blanchard S, Lee A, Nagaraj H, Wang H, Teo E,Tan E, Goh KC, Dymock B. Structure-based design of oxygen-linked macrocyclic kinase inhibitors: discovery of SB1518 and SB1578, potent inhibitors of Januskinase 2 (JAK2) and Fms-like tyrosine kinase-3 (FLT3). J Comput Aided Mol Des.2012 Apr;26(4):437-50. doi: 10.1007/s10822-012-9572-z. Epub 2012 Apr 22.PubMed PMID:22527961.

3: William AD, Lee AC, Poulsen A, Goh KC, Madan B, Hart S, Tan E, WangH, Nagaraj H, Chen D, Lee CP, Sun ET, Jayaraman R, Pasha MK, Ethirajulu K, Wood JM,Dymock BW. Discovery of the macrocycle (9E)-15-(2-(pyrrolidin-1-yl)ethoxy)-7,12,25-trioxa-19,21,24-triaza-tetracyclo[18. 3.1.1(2,5).1(14,18)]hexacosa-1(24),2,4,9,14(26),15,17,20,22-nonaene(SB1578), a potent inhibitor of janus kinase 2/fms-like tyrosine kinase-3(JAK2/FLT3) for the treatment of rheumatoid arthritis. J Med Chem. 2012 Mar22;55(6):2623-40. doi: 10.1021/jm201454n. Epub 2012 Mar 6. PubMed PMID: 22339472.

(Last updated: 4/20/2016).