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

ChemBase编号:72697
分子式:C18H23FN2O5S
平均质量:398.4490232
单一同位素质量:398.13117107
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-2-[({4-[(3-fluorophenyl)methoxy]phenyl}methyl)amino]propanamide; methanesulfonic acid
IUPAC传统名
methanesulfonic acid; safinamide
safinamide mesylate
别名
(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号
202825-46-5
MDL号
MFCD15145475
PubChem SID
162037618
PubChem CID
3038502

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 3038502 external link

理论计算性质

理论计算性质

JChem
Acid pKa 15.758402  质子受体
质子供体 LogD (pH = 5.5) -0.12634736 
LogD (pH = 7.4) 1.6006964  Log P 2.4809034 
摩尔折射率 82.9989 cm3 极化性 32.18643 Å3
极化表面积 64.35 Å2 可自由旋转的化学键
里宾斯基五规则 true 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
DMSO expand 查看数据来源
H2O: ≥15 mg/mL expand 查看数据来源
外观
white to tan powder expand 查看数据来源
比旋光度
[α]/D +9.5 to +14°, c = 1 (95% acetic acid) expand 查看数据来源
保存条件
-20°C expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
作用靶点
MAO expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
成盐信息
Mesylate expand 查看数据来源
Empirical Formula (Hill Notation)
C17H19FN2O2 · xCH4O3S expand 查看数据来源

详细说明

详细说明

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.

参考文献

参考文献

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专利

专利

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