CAS 1744-22-5|Riluzole|6-(trifluoromethoxy)-1,3-benzothiazol-2-amine|Riluzole HCl|Rilutek|riluzole|riluzole|Riluzole(Rilutek)|RP-54274|Rilutek|PK-26124|2-Amino-6-trifluoro-methoxybenzothiazole|6-(Tr...

基本信息

化学结构

分子式

C₈H₅F₃N₂OS

分子量

234.1983096

精确质量

234.00746845

电荷

InChI

InChI=1S/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13)

InChIKey

FTALBRSUTCGOEG-UHFFFAOYSA-N

Canonic Smiles

Nc1nc2c(s1)cc(cc2)OC(F)(F)F

Isomeric Smiles

s1c2c(nc1N)ccc(OC(F)(F)F)c2

计算属性

JChem

Acid pKa

16.440592

质子受体

质子供体

LogD (pH = 5.5)

3.353241

LogD (pH = 7.4)

3.3992848

Log P

3.3999074

摩尔折射率

44.3727

极化性

18.69663

极化表面积

48.14

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.83

LOG S

-3.77

溶解度

3.95e-02 g/l

数据来源

名称和标识

IUPAC传统名

riluzole 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

IUPAC标准名

6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

商标名

RilutekRiluzole HCl

别名

riluzoleRiluzolePK-26124RilutekRP-54274Riluzole(Rilutek)2-Amino-6-trifluoro-methoxybenzothiazole6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine2-Amino-6-(trifluoromethoxy)-1,3-benzothiazole 97%6-(trifluoromethoxy)benzo[d]thiazol-2-amineRiluzole2-Amino-6-(trifluoromethoxy)benzothiazole6-(Trifluoromethoxy)-2-aminobenzothiazole6-(Trifluoromethoxy)-2-benzothiazolamine2-Amino-6-(trifluoromethoxy)benzothiazole6-Trifluoromethoxy-benzothiazol-2-ylamine6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

名称和标识

数据登录号

CAS号

1744-22-5

PubChem CID

5070

PubChem SID

4650809424278006160964083

MDL号

MFCD00210213

数据登录号

化合物性质

药理学性质

rat ... Scnn1g(24768)

Glutamate transporter activation

Sodium channel blockade

High-voltage calcium channel blockade

N-methyl-D-aspartate (NMDA)/glutamate receptor antagonism

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

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描述信息

DrugBank

DB00740

Drug Groups

approved; investigational

Description

A glutamate antagonist (receptors, glutamate) used as an anticonvulsant (anticonvulsants) and to prolong the survival of patients with amyotrophic lateral sclerosis. [PubChem]

Indication

For the treatment of amyotrophic lateral sclerosis (ALS, Lou Gehrig's Disease)

Pharmacology

Riluzole, a member of the benzothiazole class, is indicated for the treatment of patients with amyotrophic lateral sclerosis (ALS). Riluzole extends survival and/or time to tracheostomy. It is also neuroprotective in various in vivo experimental models of neuronal injury involving excitotoxic mechanisms. The etiology and pathogenesis of amyotrophic lateral sclerosis (ALS) are not known, although a number of hypotheses have been advanced. One hypothesis is that motor neurons, made vulnerable through either genetic predisposition or environmental factors, are injured by glutamate. In some cases of familial ALS the enzyme superoxide dismutase has been found to be defective.

Affected Organisms

Humans and other mammals

Biotransformation

Riluzole is extensively metabolized to six major and a number of minor metabolites, which have not all been identified to date. Metabolism is mostly hepatic, consisting of cytochrome P450–dependent hydroxylation and glucuronidation. CYP1A2 is the primary isozyme involved in N-hydroxylation; CYP2D6, CYP2C19, CYP3A4, and CYP2E1 are considered unlikely to contribute significantly to riluzole metabolism in humans.

Absorption

Riluzole is well-absorbed (approximately 90%), with average absolute oral bioavailability of about 60% (CV=30%). A high fat meal decreases absorption, reducing AUC by about 20% and peak blood levels by about 45%.

Half Life

The mean elimination half-life of riluzole is 12 hours (CV=35%) after repeated doses.

Protein Binding

96% bound to plasma proteins, mainly to albumin and lipoprotein over the clinical concentration range.

References

• Song JH, Huang CS, Nagata K, Yeh JZ, Narahashi T: Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels. J Pharmacol Exp Ther. 1997 Aug;282(2):707-14. [Pubmed]

• Coric V, Taskiran S, Pittenger C, Wasylink S, Mathalon DH, Valentine G, Saksa J, Wu YT, Gueorguieva R, Sanacora G, Malison RT, Krystal JH: Riluzole augmentation in treatment-resistant obsessive-compulsive disorder: an open-label trial. Biol Psychiatry. 2005 Sep 1;58(5):424-8. [Pubmed]

• van Kan HJ, Groeneveld GJ, Kalmijn S, Spieksma M, van den Berg LH, Guchelaar HJ: Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. Br J Clin Pharmacol. 2005 Mar;59(3):310-3. [Pubmed]

• Zarate CA Jr, Payne JL, Quiroz J, Sporn J, Denicoff KK, Luckenbaugh D, Charney DS, Manji HK: An open-label trial of riluzole in patients with treatment-resistant major depression. Am J Psychiatry. 2004 Jan;161(1):171-4. [Pubmed]

• Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. Epub 2008 Jan 2. [Pubmed]

• Lamanauskas N, Nistri A: Riluzole blocks persistent Na+ and Ca2+ currents and modulates release of glutamate via presynaptic NMDA receptors on neonatal rat hypoglossal motoneurons in vitro. Eur J Neurosci. 2008 May;27(10):2501-14. Epub 2008 Apr 26. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

描述信息

参考文献

PubChem文献

数据源提供

• Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. Epub 2008 Jan 2. Pubmed

• http://en.wikipedia.org/wiki/Riluzole

• Mantz, et al., Eur. J. Pharmacol. , 257 : R7, (1994).

• Mizoule, J., et al.: Neuropharmacology, 24, 767 (1985)

• Wahl, F., et al.: Eur. J. Pharmacol., 230, 209 (1993) Bensimon, G., et al.: N. Engl. J. Med., 330, 585 (1994)

• Rowland, L.P., N. Engl. J. Med., 1994, 330, 636

• Mantz, J., CNS Drug Rev., 1996, 2, 40, (rev)

• Yagupol'skii, L.M. et al., Zh. Obshch. Khim., 1963, 33, 2301, (synth)

• Tsai, C. et al., Neurol. Neurobiol., 1987, 24, 79, (pharmacol)

• Eur. Pat., 1982, Pharmindustrie, 50 551; CA, 97, 44352, (pharmacol)

• Bensimon, G. et al., N. Engl. J. Med., 1994, 330, 585, (clin trial)

• Mizoule, J. et al., Neuropharmacology, 1985, 24, 767, (pharmacol)

• Mantz, J. et al., Eur. J. Pharmacol., 1994, 257, R7, (pharmacol)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC传统名

riluzole 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

IUPAC标准名

6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

商标名

RilutekRiluzole HCl

别名

数据登录号

CAS号

1744-22-5

PubChem CID

5070

PubChem SID

4650809424278006160964083

MDL号

MFCD00210213

参考文献

PubChem文献

数据源提供

• Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. Epub 2008 Jan 2. Pubmed

• http://en.wikipedia.org/wiki/Riluzole

• Mantz, et al., Eur. J. Pharmacol. , 257 : R7, (1994).

• Mizoule, J., et al.: Neuropharmacology, 24, 767 (1985)

• Wahl, F., et al.: Eur. J. Pharmacol., 230, 209 (1993) Bensimon, G., et al.: N. Engl. J. Med., 330, 585 (1994)

• Rowland, L.P., N. Engl. J. Med., 1994, 330, 636

• Mantz, J., CNS Drug Rev., 1996, 2, 40, (rev)

• Yagupol'skii, L.M. et al., Zh. Obshch. Khim., 1963, 33, 2301, (synth)

• Tsai, C. et al., Neurol. Neurobiol., 1987, 24, 79, (pharmacol)

• Eur. Pat., 1982, Pharmindustrie, 50 551; CA, 97, 44352, (pharmacol)

• Bensimon, G. et al., N. Engl. J. Med., 1994, 330, 585, (clin trial)

• Mizoule, J. et al., Neuropharmacology, 1985, 24, 767, (pharmacol)

• Mantz, J. et al., Eur. J. Pharmacol., 1994, 257, R7, (pharmacol)

生物活性

PubChem BioAssay

化合物性质

药理学性质

rat ... Scnn1g(24768)

Glutamate transporter activation

Sodium channel blockade

High-voltage calcium channel blockade

N-methyl-D-aspartate (NMDA)/glutamate receptor antagonism

描述信息

DrugBank

DB00740

Drug Groups

approved; investigational

Description

A glutamate antagonist (receptors, glutamate) used as an anticonvulsant (anticonvulsants) and to prolong the survival of patients with amyotrophic lateral sclerosis. [PubChem]

Indication

For the treatment of amyotrophic lateral sclerosis (ALS, Lou Gehrig's Disease)

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Half Life

The mean elimination half-life of riluzole is 12 hours (CV=35%) after repeated doses.

Protein Binding

96% bound to plasma proteins, mainly to albumin and lipoprotein over the clinical concentration range.

References

• Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. Epub 2008 Jan 2. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

化合物信息

ID:620