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202825-46-5 molecular structure
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(2S)-2-[({4-[(3-fluorophenyl)methoxy]phenyl}methyl)amino]propanamide; methanesulfonic acid

ChemBase ID: 72697
Molecular Formular: C18H23FN2O5S
Molecular Mass: 398.4490232
Monoisotopic Mass: 398.13117107
SMILES and InChIs

SMILES:
c1(cccc(c1)COc1ccc(cc1)CN[C@H](C(=O)N)C)F.CS(=O)(=O)O
Canonical SMILES:
CS(=O)(=O)O.NC(=O)[C@@H](NCc1ccc(cc1)OCc1cccc(c1)F)C
InChI:
InChI=1S/C17H19FN2O2.CH4O3S/c1-12(17(19)21)20-10-13-5-7-16(8-6-13)22-11-14-3-2-4-15(18)9-14;1-5(2,3)4/h2-9,12,20H,10-11H2,1H3,(H2,19,21);1H3,(H,2,3,4)/t12-;/m0./s1
InChIKey:
YKOCHIUQOBQIAC-YDALLXLXSA-N

Cite this record

CBID:72697 http://www.chembase.cn/molecule-72697.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-[({4-[(3-fluorophenyl)methoxy]phenyl}methyl)amino]propanamide; methanesulfonic acid
IUPAC Traditional name
methanesulfonic acid; safinamide
safinamide mesylate
Synonyms
(S)-(+)-2-[[4-(3-Fluorobenzoxy)benzyl]amino]propanamide; (S)-2-[[4-[(3-Fluorobenzyl)oxy]benzyl]amino]propanamide; FCE-26743; PNU-151774E, NW-1015;
Safinamide mesylate salt
FCE-28073(R-isomer)
PNU-151774E
NW-1015
Safinamide Mesylate(FCE28073)
CAS Number
202825-46-5
MDL Number
MFCD15145475
PubChem SID
162037618
PubChem CID
3038502

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 3038502 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 15.758402  H Acceptors
H Donor LogD (pH = 5.5) -0.12634736 
LogD (pH = 7.4) 1.6006964  Log P 2.4809034 
Molar Refractivity 82.9989 cm3 Polarizability 32.18643 Å3
Polar Surface Area 64.35 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
H2O: ≥15 mg/mL expand Show data source
Apperance
white to tan powder expand Show data source
Optical Rotation
[α]/D +9.5 to +14°, c = 1 (95% acetic acid) expand Show data source
Storage Condition
-20°C expand Show data source
MSDS Link
Download expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
MAO expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Mesylate expand Show data source
Empirical Formula (Hill Notation)
C17H19FN2O2 · xCH4O3S expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S1472 external link
Research Area
Description Neurological Disease
Biological Activity
Description Safinamide Mesylate is mesylate salt of Safinamide, which selectively and reversibly inhibits MAO-B with IC50 of 0.45 μM.
Targets MAO-B
IC50 0.45 μM [3]
In Vitro Safinamide is a highly selective MAO-B inhibitor in rat brain mitochondria, with an IC50 of 98 nM. safinamide inhibits MAO-B in human brain with an IC50 of 9 nM. Safinamide has high affinity for the Na+ channel-binding site II in rat cortical membranes, with an IC50 of 8 μM. Safinamide inhibits the fast Na+ currents in a concentration- and state-dependent manner in rat cortical neurons. Safinamide blocks N-Type Ca2+ currents in rat cortical neurons with IC50 23 μM. Safinamide inhibits glutamate release induced by depolarizing conditions in rat hippocampal synaptosomes with IC50 of 9 μM. Safinamide incubated 1 hour before veratridine reduces the neuron damage with an IC50 1.4 μM through blockade of opening voltage-dependent Na+ and Ca2+ channels in rat primary cortical neurons. [1] Safinamide binds to human MAO B with a Ki of 0.5 μM. Safinamide binds to human MAO B in an extended conformation occupying both flavin and entrance cavity. [2]
In Vivo Safinamide orally administrated dose-dependently inhibits mouse brain MAO-B with IC50 of 0.6 mg/kg, and MAO-B activity recovers quickly, starting from 8 hours. Safinamide significantly inhibits cell body degeneration in the substantia nigra pars compacta. Safinamide intraperitoneally administered 15 minutes before kainic acid protects against hippocampal neuron loss, starting at 10 mg/kg showing neuroprotective properties. Safinamide intraperitoneally administrated at dose of 100 mg/kg shows a relevant neurorescuing effect on hippocampal neurons when given 3 hours after ischemia. Safinamide has a high oral bioavailability (80–92%), is rapidly absorbed in plasma after reaching the peak within 0.5–2 hours declines, with a terminal half-life of about 3, 7, and 13 hours in mice, rats, and monkeys, respectively. [1]
Clinical Trials Safinamide is currently in a Phase II clinical trial in Parkinson's Disease.
Features 5000-fold more potent in inhibiting MAO-B versus MAO-A
Combination Therapy
Description Safinamide intraperitoneally administrated at dose of 20 mg/kg significantly increases DA levels (60%) when coadministered with levodopa (100 mg/kg IP) and benserazide (12.5 mg/kg IP) in DA-depleted C57BL mice 15 days after MPTP treatment. [1]
Protocol
Kinase Assay [3]
Enzyme Activity Assay The enzyme activities are assessed with a radioenzymatic assay using the selective substrates 14C-phenylethylamine (PEA) for MAO-B. The mitochondrial pellet (500 μg protein) is resuspended in 200 μL of 0.1 M phosphate buffer, pH 7.40, and is added to 50 μL of the solution of safinamide or of buffer and incubated for 30 min at 37 °C (preincubation). Then the substrate in 50 μL of 0.5 μM 14CPEA is added and the assay mixture is incubated at 37 °C for 10 min. The reaction is stopped by adding 0.2 mL of perchloric acid. After centrifugation, the acidic radioactive metabolites are extracted with 3 mL of toluene and the radioactivity of the organic phase is measured by liquid scintillation spectrometry at 90% efficiency. The enzymatic activity is expressed as nanomoles of substrate transformed per milligram of protein per minute (nmol mg-1 min-1). Safinamide inhibition curves are obtained from five to eight different concentrations (10-10-10-5 M), each in duplicate, and the IC50 is determined using nonlinear regression analysis.
Animal Study [2]
Animal Models DA-depleted C57BL mice
Formulation sterile 0.9% sodium chloride solution
Doses 20 mg/kg
Administration Inject intraperitoneally in a single dose
References
[1] Caccia C, et al. Neurology, 2006, 67(7 Suppl 2), S18-23.
[2] Binda C, et al. J Med Chem, 2007, 50(23), 5848-5852.
[3] Leonetti F, et al. J Med Chem, 2007, 50(20), 4909-4916.
Sigma Aldrich - SML0025 external link
Biochem/physiol Actions
Safinamide is a highly selective and reversible monoamine oxidase type B (MAO-B) inhibitor that increases neostriatal dopamine concentration. In addition, safinamide is voltage-dependent sodium and calcium channel blocker. It appears to bind to the batrachotoxin-sensitive site 2 of the voltage-sensitive sodium channels. Safinamide blocks N and L-type calcium channels and inhibits glutamate and aspartate release from synaptic terminals.

REFERENCES

REFERENCES

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