Umibecestat free base | CNP-520 | CAS# 1387560-01-1 | beta-secretase inhibitor

MedKoo Cat#: 572152 | Name: Umibecestat free base

Description:

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

Umibecestat, also known as CNP-520, is a beta-secretase inhibitor and is a drug candidate for prevention trials in Alzheimer's disease. CNP520 has a selectivity, pharmacodynamics, and distribution profile suitable for AD prevention studies. CNP520 reduced brain and cerebrospinal fluid (CSF) Aβ in rats and dogs, and Aβ plaque deposition in APP-transgenic mice. CNP520 reduces Aβ load and neuroinflammation in APP‐transgenic mice

Chemical Structure

Umibecestat free base

CAS#1387560-01-1 (free base)

Theoretical Analysis

MedKoo Cat#: 572152

Name: Umibecestat free base

CAS#: 1387560-01-1 (free base)

Chemical Formula: C19H15ClF7N5O2

Exact Mass: 513.0802

Molecular Weight: 513.80

Elemental Analysis: C, 44.42; H, 2.94; Cl, 6.90; F, 25.88; N, 13.63; O, 6.23

Price and Availability

Size	Price	Availability
25mg	USD 1,650.00	2 Weeks
50mg	USD 2,950.00	2 Weeks
100mg	USD 5,250.00	2 Weeks

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Related CAS #

1387560-01-1 (free base) 2365306-62-1 (HCl) 2365306-56-3 (fumarate) 2365306-58-5 (tatrate) 2365306-75-6 (citrate)

Synonym

Umibecestat; CNP-520; CNP 520; CNP520;

IUPAC/Chemical Name

N-{6-[(3R,6R)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]-5-fluoropyridin-2-yl}-3-chloro-5- (trifluoromethyl)pyridine-2-carboxamide

InChi Key

PSBBWFNMHDUTRH-DLBZAZTESA-N

InChi Code

InChI=1S/C19H15ClF7N5O2/c1-16(7-34-17(2,15(28)32-16)19(25,26)27)13-10(21)3-4-11(30-13)31-14(33)12-9(20)5-8(6-29-12)18(22,23)24/h3-6H,7H2,1-2H3,(H2,28,32)(H,30,31,33)/t16-,17+/m0/s1

SMILES Code

O=C(C1=NC=C(C(F)(F)F)C=C1Cl)NC2=NC([C@]3(C)CO[C@](C(F)(F)F)(C)C(N)=N3)=C(F)C=C2

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

Shelf Life

>3 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).

HS Tariff Code

2934.99.9001

More Info

The beta-site amyloid precursor protein cleaving enzyme-1 (BACE-1) initiates the generation of amyloid-β (Aβ), and the amyloid cascade leading to amyloid plaque deposition, neurodegeneration, and dementia in Alzheimer's disease (AD).

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 513.80 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Nabi F, Ahmad O, Fatima A, Ahmad A, Sharma J, Khan RH. Small molecule inhibits BACE1 activity by a dual mechanism confirmed by simulations-based study. J Biomol Struct Dyn. 2024 Dec 5:1-13. doi: 10.1080/07391102.2024.2435641. Epub ahead of print. PMID: 39633599. 2: Tariot PN, Riviere ME, Salloway S, Burns JM, Snaedal JG, Borowsky B, Lopez CL, Liu F, Rouzade-Dominguez ML, Cazorla P, Mousseau MC, Arkuszewski M, Ricart J, Viglietta V, Sui Y, Caputo A, Langbaum JB, Reiman EM, Graf A. Reversibility of cognitive worsening observed with BACE inhibitor umibecestat in the Alzheimer's Prevention Initiative (API) Generation Studies. Alzheimers Dement. 2024 Nov;20(11):7745-7761. doi: 10.1002/alz.14237. Epub 2024 Sep 25. PMID: 39320017; PMCID: PMC11567862. 3: Riviere ME, Langbaum JB, Turner RS, Rinne JO, Sui Y, Cazorla P, Ricart J, Meneses K, Caputo A, Tariot PN, Reiman EM, Graf A. Effects of the active amyloid beta immunotherapy CAD106 on PET measurements of amyloid plaque deposition in cognitively unimpaired APOE ε4 homozygotes. Alzheimers Dement. 2024 Mar;20(3):1839-1850. doi: 10.1002/alz.13532. Epub 2023 Dec 25. PMID: 38145469; PMCID: PMC10984441. 4: Walsh T, Duff L, Riviere ME, Tariot PN, Doak K, Smith M, Borowsky B, Lopez Lopez C, Arratia PC, Liu F, Scholten I, Gordon D, Arbuckle J, Graf A, Quinn M, Ricart J, Langbaum JB. Outreach, Screening, and Randomization of APOE ε4 Carriers into an Alzheimer's Prevention Trial: A global Perspective from the API Generation Program. J Prev Alzheimers Dis. 2023;10(3):453-463. doi: 10.14283/jpad.2023.27. PMID: 37357285; PMCID: PMC10426731. 5: Machauer R, Lueoend R, Hurth K, Veenstra SJ, Rueeger H, Voegtle M, Tintelnot- Blomley M, Rondeau JM, Jacobson LH, Laue G, Beltz K, Neumann U. Discovery of Umibecestat (CNP520): A Potent, Selective, and Efficacious β-Secretase (BACE1) Inhibitor for the Prevention of Alzheimer's Disease. J Med Chem. 2021 Oct 28;64(20):15262-15279. doi: 10.1021/acs.jmedchem.1c01300. Epub 2021 Oct 14. PMID: 34648711. 6: Miranda A, Montiel E, Ulrich H, Paz C. Selective Secretase Targeting for Alzheimer's Disease Therapy. J Alzheimers Dis. 2021;81(1):1-17. doi: 10.3233/JAD-201027. PMID: 33749645. 7: Ugbaja SC, Appiah-Kubi P, Lawal MM, Gumede NS, Kumalo HM. Unravelling the molecular basis of AM-6494 high potency at BACE1 in Alzheimer's disease: an integrated dynamic interaction investigation. J Biomol Struct Dyn. 2022 Aug;40(12):5253-5265. doi: 10.1080/07391102.2020.1869099. Epub 2021 Jan 7. PMID: 33410374. 8: Ugbaja SC, Sanusi ZK, Appiah-Kubi P, Lawal MM, Kumalo HM. Computational modelling of potent β-secretase (BACE1) inhibitors towards Alzheimer's disease treatment. Biophys Chem. 2021 Mar;270:106536. doi: 10.1016/j.bpc.2020.106536. Epub 2020 Dec 26. PMID: 33387910. 9: Vormfelde SV, Pezous N, Lefèvre G, Kolly C, Neumann U, Jordaan P, Ufer M, Legangneux E. A Pooled Analysis of Three Randomized Phase I/IIa Clinical Trials Confirms Absence of a Clinically Relevant Effect on the QTc Interval by Umibecestat. Clin Transl Sci. 2020 Nov;13(6):1316-1326. doi: 10.1111/cts.12832. Epub 2020 Jul 23. PMID: 32583957; PMCID: PMC7719381. 10: Lopez Lopez C, Tariot PN, Caputo A, Langbaum JB, Liu F, Riviere ME, Langlois C, Rouzade-Dominguez ML, Zalesak M, Hendrix S, Thomas RG, Viglietta V, Lenz R, Ryan JM, Graf A, Reiman EM. The Alzheimer's Prevention Initiative Generation Program: Study design of two randomized controlled trials for individuals at risk for clinical onset of Alzheimer's disease. Alzheimers Dement (N Y). 2019 Jun 12;5:216-227. doi: 10.1016/j.trci.2019.02.005. PMID: 31211217; PMCID: PMC6562315. 11: Neumann U, Ufer M, Jacobson LH, Rouzade-Dominguez ML, Huledal G, Kolly C, Lüönd RM, Machauer R, Veenstra SJ, Hurth K, Rueeger H, Tintelnot-Blomley M, Staufenbiel M, Shimshek DR, Perrot L, Frieauff W, Dubost V, Schiller H, Vogg B, Beltz K, Avrameas A, Kretz S, Pezous N, Rondeau JM, Beckmann N, Hartmann A, Vormfelde S, David OJ, Galli B, Ramos R, Graf A, Lopez Lopez C. The BACE-1 inhibitor CNP520 for prevention trials in Alzheimer's disease. EMBO Mol Med. 2018 Nov;10(11):e9316. doi: 10.15252/emmm.201809316. PMID: 30224383; PMCID: PMC6220303. 12: Lopez Lopez C, Caputo A, Liu F, Riviere ME, Rouzade-Dominguez ML, Thomas RG, Langbaum JB, Lenz R, Reiman EM, Graf A, Tariot PN. The Alzheimer's Prevention Initiative Generation Program: Evaluating CNP520 Efficacy in the Prevention of Alzheimer's Disease. J Prev Alzheimers Dis. 2017;4(4):242-246. doi: 10.14283/jpad.2017.37. PMID: 29181489.