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116539-59-4 分子结构
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methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine

ChemBase编号:359
分子式:C18H19NOS
平均质量:297.41456
单一同位素质量:297.11873523
SMILES和InChIs

SMILES:
s1c([C@@H](Oc2c3c(ccc2)cccc3)CCNC)ccc1
Canonical SMILES:
CNCC[C@@H](c1cccs1)Oc1cccc2c1cccc2
InChI:
InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1
InChIKey:
ZEUITGRIYCTCEM-KRWDZBQOSA-N

引用这个纪录

CBID:359 http://www.chembase.cn/molecule-359.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
methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine
IUPAC传统名
duloxetine
商标名
Cymbalta
Yentreve
别名
(+-)-duloxetine
Duloxetine HCl
Duloxetine Hydrochloride
Duloxetine
CAS号
116539-59-4
136434-34-9
PubChem SID
46507937
160963822
PubChem CID
60835
CHEBI ID
36795
ATC码
N06AX21
CHEMBL
1175
Chemspider ID
54822
DrugBank ID
DB00476
IUPHAR配体索引
202
KEGG ID
D07880
美国药典/FDA物质标识码
O5TNM5N07U
维基百科标题
Duloxetine
Medline Plus
a604030

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 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 1.0008107  LogD (pH = 7.4) 1.9402544 
Log P 4.197729  摩尔折射率 87.7339 cm3
极化性 35.708214 Å3 极化表面积 21.26 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 4.72  LOG S -5.0 
溶解度 2.96e-03 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
溶解度
0.00296 mg/mL [Predicted by ALOGPS] expand 查看数据来源
疏水性(logP)
4 expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
~ 50% (32% to 80%) expand 查看数据来源
排泄
70% in urine, 20% in feces expand 查看数据来源
半衰期
12.1 hours expand 查看数据来源
代谢
Liver, two P450 isozymes, CYP2D6 and CYP1A2 expand 查看数据来源
蛋白结合率
~ 95% expand 查看数据来源
法定药品分级
Rx-only (US) expand 查看数据来源
妊娠期药物分类
C (US) expand 查看数据来源
美国(FDA)药品许可证
duloxetine expand 查看数据来源
欧盟(EMEA)药品许可证
Ariclaim expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00476 external link
Item Information
Drug Groups approved
Description Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). It is manufactured and marketed by Eli Lilly and Company.

Duloxetine has not yet been FDA approved for stress urinary incontinence or for fibromyalgia.

Duloxetine is a selective SNRI (selective serotonin-norepinephrine reuptake inhibitor). Duloxetine is a systemic drug therapy which affects the body as a whole. Known also under the code name LY248686, it is a potent dual reuptake inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE), possessing comparable affinities in binding to NE- and 5-HT transporter sites. It is a less potent inhibitor of dopamine reuptake.
Indication For the acute and maintenance treatment of major depressive disorder (MDD), as well as acute management of generalized anxiety disorder. Also used for the management of neuropathic pain associated with diabetic peripheral neuropathy, and fibromyalgia. Has been used in the management of moderate to severe stress urinary incontinence (SUI) in women.
Pharmacology Duloxetine is in a class of medications called selective serotonin and norepinephrine reuptake inhibitors (SSNRIs) and primarily targets major depressive disorders (MDD) and stress urinary incontinence (SUI). Duloxetine is also used to treat pain and tingling caused by diabetic neuropathy (damage to nerves that can develop in people who have diabetes). Known also as LY248686, it is a potent dual inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake, possessing comparable affinities in binding to NE and 5-HT transport sites. Interestingly, its behavior contrasts to most other dual-reuptake inhibitors. Furthermore, duloxentine lacks affinity for monoamine receptors within the central nervous system.
Toxicity Oral, rat LD50: 491 mg/kg for males and 279 mg/kg for females. Symptoms of overdose include tremors, convulsions, reduced activity, slow pupillary response, intermittent tremors, and rigidity.
Affected Organisms
Humans and other mammals
Biotransformation The major biotransformation pathways for duloxetine involve oxidation of the naphthyl ring followed by conjugation and further oxidation. Both CYP2D6 and CYP1A2 catalyze the oxidation of the naphthyl ring in vitro. Metabolites found in plasma include 4-hydroxy duloxetine glucuronide and 5-hydroxy, 6-methoxy duloxetine sulfate. The major circulating metabolites have not been shown to contribute significantly to the pharmacologic activity of duloxetine.
Absorption Orally administered duloxetine hydrochloride is well absorbed.
Half Life 12 hours (range 8-17 hours)
Protein Binding Protein binding is greater than 90%.
Elimination Many additional metabolites have been identified in urine, some representing only minor pathways of elimination. Most (about 70%) of the duloxetine dose appears in the urine as metabolites of duloxetine; about 20% is excreted in the feces.
Distribution * 1640 L
References
Turcotte JE, Debonnel G, de Montigny C, Hebert C, Blier P: Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. Neuropsychopharmacology. 2001 May;24(5):511-21. [Pubmed]
Anttila S, Leinonen E: Duloxetine Eli Lilly. Curr Opin Investig Drugs. 2002 Aug;3(8):1217-21. [Pubmed]
Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. [Pubmed]
van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. [Pubmed]
Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. [Pubmed]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Anttila S, Leinonen E: Duloxetine Eli Lilly. Curr Opin Investig Drugs. 2002 Aug;3(8):1217-21. Pubmed
  • Turcotte JE, Debonnel G, de Montigny C, Hebert C, Blier P: Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. Neuropsychopharmacology. 2001 May;24(5):511-21. Pubmed
  • Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. Pubmed
  • van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. Pubmed
  • Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. Pubmed
  • Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. Pubmed
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专利

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