Verubecestat - CAS 1286770-55-5
Catalog number: B0084-474106
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C17H17F2N5O3S
Molecular Weight:
409.41
COA:
Inquire
Targets:
β-secretase
Description:
Verubecestat, a iminothiadiazine dioxide compound, is an oral BACE1 inhibitor originated by Merck & Co. It can bind significantly to β-secretase. Verubecestat has the potent effect to treat Alzheimer's disease and is currently in Phase III clinical trials.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-474106 50 mg $198 In stock
Bulk Inquiry
Purity:
98%
Appearance:
powder
Synonyms:
N-[3-[(5R)-3-amino-2,5-dimethyl-1,1-dioxo-6H-1,2,4-thiadiazin-5-yl]-4-fluorophenyl]-5-fluoropyridine-2-carboxamide; J1I0P6WT7T; Verubecestat; UNII-J1I0P6WT7T; J1I0P6WT7T; 1286770-55-5; Verubecestat [USAN]; Verubecestat (USAN/INN); GTPL8699; CHEMBL3301601; SCHEMBL10328722; SCHEMBL17507398; BDBM143220; example 25 (US8940748); SCH-900931; D10739; US8940748, 25; 2-Pyridinecarboxamide, N-(3-((5R)-3-amino-5,6-dihydro-2,5-dimethyl-1,1-dioxido-2H-1,2,4-thiadiazin-5-yl)-4-fluorophenyl)-5-fluoro-; N-(3-((5R)-3-amino-2,5-dimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6,2,4-thiadiazin-5-yl)-4-fluorophenyl)-5-fluoropyridine-2-carboxamide; N-(3-((5R)-3-amino-2,5-dimethyl-1,1-dioxo-5,6-dihydro-2H-1lambda6,2,4-thiadiazin-5-yl)-4-fluorophenyl)-5-fluoropyridine-2-carboxamide; N-[3-[(5R)-3-amino-2,5-dimethyl-1,1-dioxo-6H-1,2,4-thiadiazin-5-yl]-4-fluorophenyl]-5-fluoropyridine-2-carboxamide
Solubility:
DMSO ≥ 35 mg/Ml
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Alzheimer's disease
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
Density:
1.52±0.1 g/cm3
InChIKey:
YHYKUSGACIYRML-KRWDZBQOSA-N
InChI:
1S/C17H17F2N5O3S/c1-17(9-28(26,27)24(2)16(20)23-17)12-7-11(4-5-13(12)19)22-15(25)14-6-3-10(18)8-21-14/h3-8H,9H2,1-2H3,(H2,20,23)(H,22,25)/t17-/m0/s1
Canonical SMILES:
CC1(CS(=O)(=O)N(C(=N1)N)C)C2=C(C=CC(=C2)NC(=O)C3=NC=C(C=C3)F)F
Current Developer:
Originator Merck & Co
1.Future Therapeutics in Alzheimer's Disease: Development Status of BACE Inhibitors.
Evin G BioDrugs. 2016 Jun;30(3):173-94. doi: 10.1007/s40259-016-0168-3.
Alzheimer's disease (AD) is the primary cause of dementia in the elderly. It remains incurable and poses a huge socio-economic challenge for developed countries with an aging population. AD manifests by progressive decline in cognitive functions and alterations in behaviour, which are the result of the extensive degeneration of brain neurons. The AD pathogenic mechanism involves the accumulation of amyloid beta peptide (Aβ), an aggregating protein fragment that self-associates to form neurotoxic fibrils that trigger a cascade of cellular events leading to neuronal injury and death. Researchers from academia and the pharmaceutical industry have pursued a rational approach to AD drug discovery and targeted the amyloid cascade. Schemes have been devised to prevent the overproduction and accumulation of Aβ in the brain. The extensive efforts of the past 20 years have been translated into bringing new drugs to advanced clinical trials. The most progressed mechanism-based therapies to date consist of immunological interventions to clear Aβ oligomers, and pharmacological drugs to inhibit the secretase enzymes that produce Aβ, namely β-site amyloid precursor-cleaving enzyme (BACE) and γ-secretase.
2.Synthesis of Verubecestat, a BACE1 Inhibitor for the Treatment of Alzheimer's Disease.
Thaisrivongs DA;Miller SP;Molinaro C;Chen Q;Song ZJ;Tan L;Chen L;Chen W;Lekhal A;Pulicare SK;Xu Y Org Lett. 2016 Nov 18;18(22):5780-5783. Epub 2016 Nov 4.
Verubecestat is an inhibitor of β-secretase being evaluated for the treatment of Alzheimer's disease. The first-generation route relies on an amide coupling with a functionalized aniline, the preparation of which introduces synthetic inefficiencies. The second-generation route replaces this with a copper-catalyzed C-N coupling, allowing for more direct access to the target. Other features of the new route include a diastereoselective Mannich-type addition into an Ellman sulfinyl ketimine and a late-stage guanidinylation.
3.Emerging drugs to reduce abnormal β-amyloid protein in Alzheimer's disease patients.
Panza F;Seripa D;Solfrizzi V;Imbimbo BP;Lozupone M;Leo A;Sardone R;Gagliardi G;Lofano L;Creanza BC;Bisceglia P;Daniele A;Bellomo A;Greco A;Logroscino G Expert Opin Emerg Drugs. 2016 Dec;21(4):377-391. Epub 2016 Oct 6.
Currently available drugs against Alzheimer's disease (AD) target cholinergic and glutamatergic neurotransmissions without affecting the underlying disease process. Putative disease-modifying drugs are in development and target β-amyloid (Aβ) peptide and tau protein, the principal neurophatological hallmarks of the disease. Areas covered: Phase III clinical studies of emerging anti-Aβ drugs for the treatment of AD were searched in US and EU clinical trial registries and in the medical literature until May 2016. Expert opinion: Drugs in Phase III clinical development for AD include one inhibitor of the β-secretase cleaving enzyme (BACE) (verubecestat), three anti-Aβ monoclonal antibodies (solanezumab, gantenerumab, and aducanumab), an inhibitor of receptor for advanced glycation end products (RAGE) (azeliragon) and the combination of cromolyn sodium and ibuprofen (ALZT-OP1). These drugs are mainly being tested in subjects during early phases of AD or in subjects at preclinical stage of familial AD or even in asymptomatic subjects at high risk of developing AD. The hope is to intervene in the disease process when it is not too late. However, previous clinical failures with anti-Aβ drugs and the lack of fully understanding of the pathophysiological role of Aβ in the development of AD, put the new drugs at substantial risk of failure.
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CAS 1286770-55-5 Verubecestat

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