APR-246
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 205945

CAS#: 5291-32-7

Description: APR-246, also known as PRIMA-1MET, 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

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10mg
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100mg
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1g
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10g
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25mg
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200mg
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2g
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20g
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50mg
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500mg
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5g
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APR-246, 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

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Theoretical Analysis

MedKoo Cat#: 205945
Name: APR-246
CAS#: 5291-32-7
Chemical Formula: C10H17NO3
Exact Mass: 199.12084
Molecular Weight: 199.24688
Elemental Analysis: C, 60.28; H, 8.60; N, 7.03; O, 24.09


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

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

Appearance:
Solid powder

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

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:
>5 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

  
 
 
 


References

1: Shalom-Feuerstein R, Serror L, Aberdam E, Müller FJ, van Bokhoven H, Wiman KG, Zhou H, Aberdam D, Petit I. Impaired epithelial differentiation of induced pluripotent stem cells from ectodermal dysplasia-related patients is rescued by the small compound APR-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, Zhang Q, Tjabringa GS, Gilissen C, van Heeringen SJ, Schalkwijk J, van Bokhoven H, Wiman KG, Zhou H. APR-246/PRIMA-1MET rescues epidermal differentiation in skin keratinocytes derived from EEC syndrome patients with 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-targeting compound APR-246 in refractory hematologic malignancies and prostate cancer. 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 delay in small cell lung cancer expressing mutant p53. Clin Cancer Res. 2011 May 1;17(9):2830-41. doi: 10.1158/1078-0432.CCR-10-3168. Epub 2011 Mar 17. 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-type p53-dependent suppression of malignant melanoma tumor growth in 3D culture and in vivo. Cell Cycle. 2011 Jan 15;10(2):301-7. Epub 2011 Jan 15. 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 with conventional chemotherapeutic drugs in acute myeloid leukemia cells. Eur J 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 and p73. Oncogene. 2010 Dec 9;29(49):6442-51. doi: 10.1038/onc.2010.382. Epub 2010 Sep 6. PubMed PMID: 20818419.