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79559-97-0 分子结构
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(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

ChemBase编号:975
分子式:C17H17Cl2N
平均质量:306.22958
单一同位素质量:305.07380491
SMILES和InChIs

SMILES:
Clc1cc([C@@H]2CC[C@H](NC)c3c2cccc3)ccc1Cl
Canonical SMILES:
CN[C@H]1CC[C@H](c2c1cccc2)c1ccc(c(c1)Cl)Cl
InChI:
InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1
InChIKey:
VGKDLMBJGBXTGI-SJCJKPOMSA-N

引用这个纪录

CBID:975 http://www.chembase.cn/molecule-975.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
(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
IUPAC传统名
sertraline
商标名
Apo-Sertraline
Lustral
Zoloft
Zoloft, Lustral, Daxid, Altruline, Besitran, Deprax, Elrval, Emergen, Gladem, Implicane, Sedoran, Sealdin, SerivoLowfin, Stimuloton, Tresleen, Sertralin Bluefish
别名
Sertralina [Spanish]
Sertraline Hydrochloride
Sertralinum [Latin]
Sultamicillin Tosylate
Sertraline
(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
SERTRALINE HYDROCHLORIDE
CAS号
79559-97-0
79617-96-2
PubChem SID
160964438
99445038
46505341
PubChem CID
68617
CHEBI ID
9123
ATC码
N06AB06
CHEMBL
809
Chemspider ID
61881
DrugBank ID
DB01104
KEGG ID
D02360
美国药典/FDA物质标识码
QUC7NX6WMB
维基百科标题
Sertraline
Medline Plus
a697048

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
苏州艾佳
AJA-O40222 external link 加入购物车 请登录

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) 1.9396342  LogD (pH = 7.4) 2.759919 
Log P 5.1493  摩尔折射率 85.741 cm3
极化性 33.5986 Å3 极化表面积 12.03 Å2
可自由旋转的化学键 里宾斯基五规则 false 
Log P 5.06  LOG S -6.32 
溶解度 1.45e-04 g/l 

分子性质

分子性质

理化性质 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
3.5mg/L expand 查看数据来源
疏水性(logP)
5.1 expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
44% expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
Approximately 26 hours expand 查看数据来源
代谢
Hepatic (N-demethylation mainly by CYP2B6) expand 查看数据来源
蛋白结合率
98.5% expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
C expand 查看数据来源
纯度
98% expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB01104 external link
Item Information
Drug Groups approved
Description Sertraline hydrochloride belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Sertraline may be used to treat major depressive disorder, obsessive-compulsive disorder (OCD), panic disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD) and social anxiety disorder (social phobia).
Indication For the management of major depressive disorder, posttraumatic stress disorder, obsessive-compulsive disorder, panic disorder with or without agoraphobia, premenstrual dysphoric disorder, social phobia, premature ejaculation, and vascular headaches.
Pharmacology Sertraline, an antidepressant drug similar to citalopram, fluoxetine, and paroxetine, is of the selective serotonin reuptake inhibitor (SSRI) type. Sertraline has one active metabolite and, like the other SSRIs, have less sedative, anticholinergic, and cardiovascular effects than the tricyclic antidepressant drugs because it does not have clinically important anticholinergic, antihistamine, or adrenergic blocking activity.
Toxicity Symptoms of toxicity include alopecia, decreased libido, diarrhea, ejaculation disorder, fatigue, insomnia, somnolence and serotonin syndrome. The most frequently observed side effects include: GI effects such as nausea, diarrhea or loose stools, dyspepsia, and dry mouth; nervous system effects such as somnolence, dizziness, insomnia, and tremor; sexual dysfunction in males (principally ejaculatory delay); and sweating.
Affected Organisms
Humans and other mammals
Biotransformation Extensively metabolized in the liver. Sertraline metabolism involves N-demethylation, N-hydroxylation, oxidative deamination, and glucuronidation of sertraline carbamic acid. Sertraline undergoes N-demethylation primarily catalyzed by cytochrome P450 (CYP) 2B6, with CYP2C19, CYP3A4 and CYP2D6 contributing to a lesser extent. Deamination occurs via CYP3A4 and CYP2C19. In vitro studies have shown that monoamine oxidase A and B may also catalyze sertraline deamination. Sertraline N-carbamoyl glucuronidation has also been observed in human liver microsomes.
Absorption The effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects administered a single dose with and without food. For the tablet, AUC was slightly increased when drug was administered with food but the Cmax was 25% greater, while the time to reach peak plasma concentration (Tmax) decreased from 8 hours post-dosing to 5.5 hours. For the oral concentrate, Tmax was slightly prolonged from 5.9 hours to 7.0 hours with food.
Half Life The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours.
Protein Binding 98% bound to serum proteins, principally to albumin and α1-acid glycoprotein
Elimination Sertraline is extensively metabolized and excretion of unchanged drug in urine is a minor route of elimination.
References
Couzin J: The brains behind blockbusters. Science. 2005 Jul 29;309(5735):728. [Pubmed]
Fabre LF, Abuzzahab FS, Amin M, Claghorn JL, Mendels J, Petrie WM, Dube S, Small JG: Sertraline safety and efficacy in major depression: a double-blind fixed-dose comparison with placebo. Biol Psychiatry. 1995 Nov 1;38(9):592-602. [Pubmed]
Kronig MH, Apter J, Asnis G, Bystritsky A, Curtis G, Ferguson J, Landbloom R, Munjack D, Riesenberg R, Robinson D, Roy-Byrne P, Phillips K, Du Pont IJ: Placebo-controlled, multicenter study of sertraline treatment for obsessive-compulsive disorder. J Clin Psychopharmacol. 1999 Apr;19(2):172-6. [Pubmed]
Brady K, Pearlstein T, Asnis GM, Baker D, Rothbaum B, Sikes CR, Farfel GM: Efficacy and safety of sertraline treatment of posttraumatic stress disorder: a randomized controlled trial. JAMA. 2000 Apr 12;283(14):1837-44. [Pubmed]
Yonkers KA, Halbreich U, Freeman E, Brown C, Endicott J, Frank E, Parry B, Pearlstein T, Severino S, Stout A, Stone A, Harrison W: Symptomatic improvement of premenstrual dysphoric disorder with sertraline treatment. A randomized controlled trial. Sertraline Premenstrual Dysphoric Collaborative Study Group. JAMA. 1997 Sep 24;278(12):983-8. [Pubmed]
Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. [Pubmed]
Murdoch D, McTavish D: Sertraline. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depression and obsessive-compulsive disorder. Drugs. 1992 Oct;44(4):604-24. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
DrugBank -  DB08567 external link
Drug information: experimental

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Brady K, Pearlstein T, Asnis GM, Baker D, Rothbaum B, Sikes CR, Farfel GM: Efficacy and safety of sertraline treatment of posttraumatic stress disorder: a randomized controlled trial. JAMA. 2000 Apr 12;283(14):1837-44. Pubmed
  • Yonkers KA, Halbreich U, Freeman E, Brown C, Endicott J, Frank E, Parry B, Pearlstein T, Severino S, Stout A, Stone A, Harrison W: Symptomatic improvement of premenstrual dysphoric disorder with sertraline treatment. A randomized controlled trial. Sertraline Premenstrual Dysphoric Collaborative Study Group. JAMA. 1997 Sep 24;278(12):983-8. Pubmed
  • Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. Pubmed
  • Murdoch D, McTavish D: Sertraline. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depression and obsessive-compulsive disorder. Drugs. 1992 Oct;44(4):604-24. Pubmed
  • Fabre LF, Abuzzahab FS, Amin M, Claghorn JL, Mendels J, Petrie WM, Dube S, Small JG: Sertraline safety and efficacy in major depression: a double-blind fixed-dose comparison with placebo. Biol Psychiatry. 1995 Nov 1;38(9):592-602. Pubmed
  • Kronig MH, Apter J, Asnis G, Bystritsky A, Curtis G, Ferguson J, Landbloom R, Munjack D, Riesenberg R, Robinson D, Roy-Byrne P, Phillips K, Du Pont IJ: Placebo-controlled, multicenter study of sertraline treatment for obsessive-compulsive disorder. J Clin Psychopharmacol. 1999 Apr;19(2):172-6. Pubmed
  • Couzin J: The brains behind blockbusters. Science. 2005 Jul 29;309(5735):728. Pubmed
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专利

专利

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