Safinamide

HCID 131682

Grundinformationen

CAS
133865-89-1
Standard-SMILES
C[C@H](NCc1ccc(OCc2cccc(F)c2)cc1)C(N)=O
InChIKey
NEMGRZFTLSKBAP-LBPRGKRZSA-N
Summenformel
C17H19FN2O2
Durchschnittliche Molmasse
302,34 g/mol
Monoisotopische Masse
302,14305607

Überblick

Safinamide is an amino acid amide.

Namen und Bezeichner

Bevorzugter Name
Safinamide
IUPAC
(2S)-2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]propanamide
Englischer Name
Safinamide
Summenformel
C17H19FN2O2
Molmasse
302.34

Namen und Synonyme

Safinamide133865-89-1(2S)-2-[[4-[(3-Fluorophenyl)methoxy]phenyl]methylamino]propanamideEMD 1195686SafinamidaFce-26743EMD-119568690ENL74SIG2-(4-(3-Fluorobenzyloxy)benzylamino)propionamideDTXCID701436700DTXSID601010282safinamidum
Weitere Namen anzeigen
(4-((3-fluorobenzyl)oxy)benzyl)-L-alanineCS-484FCE 26743SAFINAMIDSalfenamideSafranamideD4-Safinamide
(2S)-2-((4-((3-fluorophenyl)methoxy)phenyl)methylamino)propanamidefbap methanesulfonateRefChem:57040N04BD03(S)-2-((4-(3-fluorobenzoxy)benzyl)amino)propanamide603-772-2(S)-2-((4-((3-Fluorobenzyl)oxy)benzyl)amino)propanamideXadago

Datenbank-Bezeichner

CAS
133865-89-1
PubChem CID
131682
DTXSID
DTXSID601010282
ChEMBL
CHEMBL396778
ChEBI
CHEBI:134718
UNII
90ENL74SIG
EC Number
603-772-2
Nikkaji
J621.455J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,2
Polarare Oberfläche (TPSA)
64,4 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
7
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Nervous system -> Anti-parkinson drugs

Pharmaceuticals -> Listed in ZINC15

Human Drugs · 3 Einträge

Breastfeeding; Lactation; Antiparkinson Agents; Monoamine Oxidase Inhibitors;

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

Physikochemische Eigenschaften

Schmelzpunkt
208 · 208-212°
Siedepunkt
476.7 · 476.7±40.0 °C(Predicted)
Dichte
1.189 · 1.189±0.06 g/cm3(Predicted)
storage temp.
2 · under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit
Soluble in DMSO (up to 50 mg/ml).
Aggregatzustand
solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (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.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 02-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21292
Hazard Classes and CategoriesAcute Tox. 3 (90.5%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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

Sicherheitsdaten

hs_code
2924.29.7790
RTECS-Nr.
TX1457385

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

N04BD03

N - Nervous system

QN - Nervous system

Protein Binding88–90%
Mechanism of Action · 1 Eintrag

Safinamide is a unique molecule with multiple mechanisms of action and a very high therapeutic index. It combines potent, selective, and reversible inhibition of MAO-B with blockade of voltage-dependent Na+ and Ca2+ channels and inhibition of glutamate release. Safinamide has neuroprotective and neurorescuing effects in MPTP-treated mice, in the rat kainic acid, and in the gerbil ischemia model.

Biological Half-Life22 h
Metabolism/Metabolites · 1 Eintrag

The principal step is mediated by amidases which have not been identified, and produces safinamide acid. It is also metabolized to O-debenzylated safinamide and N-delkylated amine. The N-dealkylated amine is then oxidized to a carboxylic acid and finally glucuronidated. Dealkylation reactions are mediated by cytochrome P450s (CYPs), especially CYP3A4. Safinamide acid binds to organic anion transporter 3 (OAT3), but no clinical relevance of this interaction has been determined. Safinamide also binds to ABCG2 transiently. No other transporter affinities have been found in preliminary studies.

FDA Pharmacological Classification · 6 Einträge

90ENL74SIG

SAFINAMIDE

Established Pharmacologic Class [EPC] - Monoamine Oxidase Type B Inhibitor

Mechanisms of Action [MoA] - Monoamine Oxidase-B Inhibitors

Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors

Safinamide is a Monoamine Oxidase Type B Inhibitor. The mechanism of action of safinamide is as a Monoamine Oxidase-B Inhibitor and Breast Cancer Resistance Protein Inhibitor.

Anwendungen · 1 Eintrag

HistorySafinamide 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.

Anbieter100 Anbieter

兄弟科技股份有限公司0573-87006360
天津始加生物医药科技有限公司15022261580 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
Shochem(Shanghai) Co.,Ltd86-21-50800795 · [email protected]

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