Eprenetapopt (APR-246)

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

Description:APR-246, also known as PRIMA-1MET and Eprenetapopt, is a quinuclidinone derivative that targets the Wrap53 gene with potential antineoplastic activity. p53 activator APR-246 binds to and activates transcription of the Wrap53 gene, which results in an increase in WRAP53 p53 antisense transcript levels and, potentially, an increase in native p53 activity; in turn, increased p53 activity may lead to an induction of cell cycle arrest and apoptosis in tumor cells. This agent may work synergistically with other antineoplastic agents.

Price and Availability

Eprenetapopt (APR-246), purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 205945Name: Eprenetapopt (APR-246)CAS#: 5291-32-7Chemical Formula: C10H17NO3Exact Mass: 199.12084Molecular Weight: 199.24688Elemental Analysis: C, 60.28; H, 8.60; N, 7.03; O, 24.09

Synonym:APR246; APR-246; APR 246. PRIMA-1MET; Eprenetapopt;

IUPAC/Chemical Name:2-(hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one

InChi Key:BGBNULCRKBVAKL-UHFFFAOYSA-N

InChi Code:InChI=1S/C10H17NO3/c1-14-7-10(6-12)9(13)8-2-4-11(10)5-3-8/h8,12H,2-7H2,1H3

SMILES Code:O=C1C(COC)(CO)N2CCC1CC2

Technical Data

Additional Information

References

1: Shalom-Feuerstein R, Serror L, Aberdam E, MüllerFJ, van Bokhoven H, Wiman KG, Zhou H, Aberdam D, Petit I. Impairedepithelial differentiation of induced pluripotent stem cells fromectodermal dysplasia-related patients is rescued by the small compoundAPR-246/PRIMA-1MET. Proc Natl Acad Sci U S A. 2013 Feb 5;110(6):2152-6.doi: 10.1073/pnas.1201753109. Epub 2013 Jan 25. PubMed PMID: 23355677.

2: Shen J, van den Bogaard EH, Kouwenhoven EN, Bykov VJ, Rinne T, ZhangQ, Tjabringa GS, Gilissen C, van Heeringen SJ, Schalkwijk J, vanBokhoven H, Wiman KG, Zhou H. APR-246/PRIMA-1MET rescues epidermaldifferentiation in skin keratinocytes derived from EEC syndrome patientswith p63 mutations. Proc Natl Acad Sci U S A. 2013 Feb 5;110(6):2157-62.doi: 10.1073/pnas.1201993110. Epub 2013 Jan 25. PubMed PMID: 23355676.

3: Lehmann S, Bykov VJ, Ali D, Andrén O, Cherif H, Tidefelt U, Uggla B,Yachnin J, Juliusson G, Moshfegh A, Paul C, Wiman KG, Andersson PO.Targeting p53 in vivo: a first-in-human study with p53-targetingcompound APR-246 in refractory hematologic malignancies and prostatecancer. J Clin Oncol. 2012 Oct 10;30(29):3633-9. doi:10.1200/JCO.2011.40.7783. Epub 2012 Sep 10. PubMed PMID: 22965953.

4: Zandi R, Selivanova G, Christensen CL, Gerds TA, Willumsen BM,Poulsen HS. PRIMA-1Met/APR-246 induces apoptosis and tumor growth delayin small cell lung cancer expressing mutant p53. Clin Cancer Res. 2011May 1;17(9):2830-41. doi: 10.1158/1078-0432.CCR-10-3168. Epub 2011 Mar17. PubMed PMID: 21415220.

5: Bao W, Chen M, Zhao X, Kumar R, Spinnler C, Thullberg M, Issaeva N,Selivanova G, Strömblad S. PRIMA-1Met/APR-246 induces wild-typep53-dependent suppression of malignant melanoma tumor growth in 3Dculture and in vivo. Cell Cycle. 2011 Jan 15;10(2):301-7. Epub 2011 Jan15. PubMed PMID: 21239882.

6: Ali D, Jönsson-Videsäter K, Deneberg S, Bengtzén S, Nahi H, Paul C,Lehmann S. APR-246 exhibits anti-leukemic activity and synergism withconventional chemotherapeutic drugs in acute myeloid leukemia cells. EurJ Haematol. 2011 Mar;86(3):206-15. doi:10.1111/j.1600-0609.2010.01557.x. Epub 2011 Jan 11. PubMed PMID:21114538.

7: Rökaeus N, Shen J, Eckhardt I, Bykov VJ, Wiman KG, Wilhelm MT.PRIMA-1(MET)/APR-246 targets mutant forms of p53 family members p63 andp73. Oncogene. 2010 Dec 9;29(49):6442-51. doi: 10.1038/onc.2010.382.Epub 2010 Sep 6. PubMed PMID: 20818419.