Safinamide

(4-((3-fluorobenzyl)oxy)benzyl)-L-alanine · CS-484 · FCE 26743 · SAFINAMID · 603-772-2 · Safinamide · EMD 1195686 · Salfenamide

https://huagongshe.com/de/chemical/131682

Identifikatoren & physikalische Daten

CAS No.	133865-89-1
Summenformel	C17H19FN2O2
Durchschnittliche Molmasse	302,34 g/mol
Monoisotopische Masse	302,14305607 g/mol
SMILES	C[C@H](NCc1ccc(OCc2cccc(F)c2)cc1)C(N)=O
InChIKey	NEMGRZFTLSKBAP-LBPRGKRZSA-N
PubChem CID	131682
ChEMBL	CHEMBL396778
ChEBI	CHEBI:134718
EC No.	603-772-2
DTXSID	DTXSID601010282

Chemische & physikalische Eigenschaften

XLogP	2,2
Polarare Oberfläche (TPSA)	64,4
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	4
Frei drehbare Bindungen	7
Schwere Atome	22
Formalladung	0
Komplexität	346
Arzneimittel	Pharmaceuticals -> Nervous system -> Anti-parkinson drugsPharmaceuticals -> Listed in ZINC15
Human Drugs	BreastfeedingLactationAntiparkinson AgentsMonoamine Oxidase InhibitorsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine
Schmelzpunkt	208-212°
Siedepunkt	476.7±40.0 °C(Predicted)
Dichte	1.189±0.06 g/cm3(Predicted)
Lagerbedingungen	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	Soluble in DMSO (up to 50 mg/ml).
Aggregatzustand	solid
pKa (Säurekonstante)	16.03±0.50(Predicted)
Farbe	White
Merck	14,8315
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChI	InChI=1S/C17H19FN2O2/c1-12(17(19)21)20-10-13-5-7-16(8-6-13)22-11-14-3-2-4-15(18)9-14/h2-9,12,20H,10-11H2,1H3,(H2,19,21)/t12-/m0/s1
InChIKey	NEMGRZFTLSKBAP-LBPRGKRZSA-N
SMILES	C(N)(=O)[C@@H](NCC1=CC=C(OCC2=CC=CC(F)=C2)C=C1)C

Sicherheit & Vorschriften

GHS-Einstufung	DangerH301 (90.5%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P316, P305+P354+P338, P317, P321, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Status: Active Update: 02-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21292
Hazard Classes and Categories	Acute Tox. 3 (90.5%)
Hepatotoxicity	Safinamide has been reported to cause serum enzyme elevations in a small proportion of patients treated long term, although the abnormalities were usually mild and self-limiting and were usually no more frequent than with placebo or comparator agents. Safinamide has not been implicated in cases of acute liver injury, but such instances have been reported with nonspecific MAO inhibitors.
Effects During Pregnancy and Lactation	◉ Summary of Use during Lactation
Zollcode	2924.29.7790
RTECS-Nr.	TX1457385

Anwendungen & Verwendung

History

Safinamide is an α-aminoamide derivative with a multimodal mechanism of action involving both dopaminergic and non-dopaminergic properties. It increases levels of available dopamine through dopamine reuptake inhibition andMAO-B inhibition. It is a potent and reversible inhibitor of MAO-B, with significantly greater selectivity for MAO-B over MAO-A than selegiline and rasagiline. However, it also has an important and novel mode of action that involves blockade of Na+ channels andmodulation of Ca2+ channels that inhibits glutamate release and therefore may provide a level of cognitive improvement and neuroprotection. Homeostatic interactions between dopamine and glutamate are central to the normal physiology of the basal ganglia. In PD, this relationship is altered, resulting in upregulation of cortico-striatal glutamatergic function in l-dopa-induced dyskinesia. Any drug that can counteract such unbalance in glutamate function is potentially useful in controlling dyskinesias. Safinamide was originated by Farmitalia Carlo Erba, a company that was later purchased by Pharmacia. Newron Pharmaceuticals was established as a spin-off of Pharmacia in 1999 and acquired safinamide rights and intellectual property from Pharmacia Corporation. Newron originally granted Serono exclusive worldwide rights to develop, manufacture, and commercialize safinamide in 2006. However, in October 2011, Merck Serono agreed to return full global rights for safinamide to Newron. Newron then finalized a strategic collaboration and license agreement with Zambon for the worldwide development and commercialization of safinamide.