AdipoGen Life Sciences

Entacapone

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AG-CR1-3708-M0055 mgCHF 30.00

AG-CR1-3708-M02525 mgCHF 85.00

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Product Details
Synonyms	OR-611; (E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide
Product Type	Chemical
Properties
Formula	C₁₄H₁₅N₃O₅
MW	305.3
CAS	130929-57-6
RTECS	UC6316195
Purity Chemicals	≥98% (HPLC)
Appearance	Yellow powder
Solubility	Soluble in DMSO (30mg/ml), dimethylformamide (30mg/ml) or ethanol (5mg/ml). Insoluble in water.
Identity	Determined by ¹H-NMR.
InChi Key	JRURYQJSLYLRLN-BJMVGYQFSA-N
Smiles	OC1=C(O)C([N+]([O-])=O)=CC(/C=C(C#N)/C(N(CC)CC)=O)=C1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Potent FTO (fat mass and obesity-associated gene) inhibitor for in vivo studies. FTO belongs to the Fe²⁺ and α-ketoglutarate (α-KG)-dependent oxygenase family. It demethylates N⁶-adenosine-modified (m6A) sites and N⁶,2'-O-dimethyladenosine-modified (m6Am) sites of mRNA. With its demethylase activity, FTO regulates the expression of some uncharacterized genes. The transcription factor FOXO1 has been shown to be a substrate of FTO. FTO demethylated m6A sites on forkhead box protein O1 (FOXO1) mRNA to up-regulate FOXO1 expression, thereby modulating gluconeogenesis and thermogenesis explaining in part the function of FTO on metabolic disorders such as obesity and diabetes.
Potent selective and reversible catechol-O-methyltransferase (COMT) inhibitor, an enzyme involved in the metabolism of catecholamine neurotransmitters and related drugs. Entacapone is selective for COMT over monoamine oxidase A (MAO-A) and MAO-B and phenolsulphotransferase M (PST-M) and PST-P (IC50s = >50 µM). It is used for the treatment of Parkinson’s disease, administered concomittantly with levodopa and a decarboxylase inhibitor (e.g. carbidopa).
Inhibits α-synuclein aggregation in an in vitro assay and blocks α-synuclein-induced cell death in PC-12 cells.
Shown to uncouple oxidative phosphorylation and inhibit mitochondrial enzyme complexes I and IV.
Antioxidant that can scavenge toxic HOCl and ONOO^--species and inhibit oxidative stress-induced cell death.

Product References

Biochemical and pharmacological properties of a peripherally acting catechol-O-methyltransferase inhibitor entacapone: E. Nissinen, et al.; Naunyn Schmiedebergs Arch. Pharmacol. 346, 262 (1992)
Different in vivo properties of three new inhibitors of catechol O-methyltransferase in the rat: P.T. Mannisto, et al.; Br. J. Pharmacol. 105, 569 (1992)
The effect of entacapone (OR-611) on brain [18F]-6-L-fluorodopa metabolism: implications for levodopa therapy of Parkinson's disease: G.V. Sawle, et al.; Neurology 44, 1292 (1994)
Entacapone, a novel catechol-O-methyltransferase inhibitor for Parkinson's disease, does not impair mitochondrial energy production: E. Nissinen, et al.; Eur. J. Pharmacol. 340, 287 (1997)
Entacapone. A review of its use in Parkinson's disease: K.J. Holm & C.M. Spencer; Drugs 58, 159 (1999)
Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity: S. Di Giovanni, et al.; J. Biol. Chem. 285, 14941 (2010)
Entacapone is an Antioxidant More Potent than Vitamin C and Vitamin E for Scavenging of Hypochlorous Acid and Peroxynitrite, and the Inhibition of Oxidative Stress-Induced Cell Death: A.Y. Chen, et al.; Med. Sci. Monit. 22, 687 (2016)
The catechol-O-methyltransferase inhibitors tolcapone and entacapone uncouple and inhibit the mitochondrial respiratory chain in HepaRG cells: D. Grunig, et al.; Toxicol. In Vitro 42, 337 (2017)
Identification of entacapone as a chemical inhibitor of FTO mediating metabolic regulation through FOXO1: S. Peng, et al.; Sci. Transl. Med. 11, eaau7116 (2019)

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