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19794-93-5 分子结构
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2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

ChemBase编号:538
分子式:C19H22ClN5O
平均质量:371.86388
单一同位素质量:371.15128803
SMILES和InChIs

SMILES:
Clc1cc(N2CCN(CC2)CCCn2nc3n(c2=O)cccc3)ccc1
Canonical SMILES:
Clc1cccc(c1)N1CCN(CC1)CCCn1nc2n(c1=O)cccc2
InChI:
InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2
InChIKey:
PHLBKPHSAVXXEF-UHFFFAOYSA-N

引用这个纪录

CBID:538 http://www.chembase.cn/molecule-538.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
2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one
IUPAC传统名
trazodone
商标名
Beneficat
Bimaran
Desirel
Desyrel
Molipaxin
Pragmazone
Sideril
Thombran
Tombran
Trazalon
Trazodil
Trazodon
Trazolan
Trazonil
Trialodine
Trittico
Desyrel Dividose
别名
Trazodonum [INN-Latin]
Trazodona [INN-Spanish]
Trazodone Hcl
Trazodone Hydrochloride
trazodone
Trazodone
CAS号
19794-93-5
PubChem SID
160964001
46506648
PubChem CID
5533
CHEBI ID
9654
ATC码
N06AX05
CHEMBL
621
Chemspider ID
5332
DrugBank ID
DB00656
IUPHAR配体索引
213
KEGG ID
D08626
美国药典/FDA物质标识码
YBK48BXK30
维基百科标题
Trazodone
Medline Plus
a681038

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) 1.5380111  LogD (pH = 7.4) 2.9594436 
Log P 3.1318567  摩尔折射率 105.8796 cm3
极化性 39.210217 Å3 极化表面积 42.39 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 2.68  LOG S -3.11 
溶解度 2.90e-01 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
Sparigly soluble expand 查看数据来源
疏水性(logP)
2.9 expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
High expand 查看数据来源
排泄
20% feces,
80% urine
expand 查看数据来源
半衰期
3-6 hours expand 查看数据来源
代谢
Hepatic expand 查看数据来源
法定药品分级
Pharmacist only (Australia) expand 查看数据来源
POM (UK) expand 查看数据来源
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

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00656 external link
Item Information
Drug Groups approved; investigational
Description A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)
Indication For the treatment of depression.
Pharmacology Trazodone is an antidepressant and hypnotic chemically unrelated to tricyclic, tetracyclic, or other known antidepressant agents. The mechanism of trazodone's antidepressant action in man is not fully understood. In animals, trazodone selectively inhibits serotonin uptake by brain synaptosomes and potentiates the behavioral changes induced by the serotonin precursor, 5-hydroxytryptophan. Cardiac conduction effects of trazodone in the anesthetized dog are qualitatively dissimilar and quantitatively less pronounced than those seen with tricyclic antidepressants. Trazodone is not a monoamine oxidase inhibitor and, unlike amphetamine-type drugs, does not stimulate the central nervous system. In man, trazodone is well absorbed after oral administration without selective localization in any tissue. Since the clearance of trazodone from the body is sufficiently variable, in some patients trazodone may accumulate in the plasma.
Toxicity LD50=96mg/kg (i.v. in mice)
Affected Organisms
Humans and other mammals
Biotransformation Undergoes extensive hepatic metabolism via hydroxylation, N-dealkylation, N-oxidation and splitting of the pyridine ring. Cytochrome P450 (CYP) 3A4 catalyzes the formation of the major active metabolite, m-chlorophenylpiperazine (m-CPP). Metabolites may be further conjugated to glucuonic acid or glutathione. CYP2D6 is responsible for 4'-hydroxylation of m-CPP and the formation of at least one glutathione conjugates of m-CPP, a quinone imine-sulhydryl adduct. Oxotriazolopyridinpropionic acid, an inactive metabolite, and its conjugates account for about 20% of the total excreted oral dose. Less than 1% of the oral dose is excreted unchanged. Approximately 70-75% of the dose is eliminated in urine with the remainder being excreted in feces via biliary elimination.
Absorption Rapidly and almost completely absorbed following oral administration. Food may decrease the rate and extent of absorption.
Half Life Undergoes biphasic elimination with an initial phase t1/2 α of 3-6 hours and a terminal phase t1/2 β of 5-9 hours.
Protein Binding 89-95% bound to plasma proteins in vitro
References
Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [Pubmed]
Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)] Arzneimittelforschung. 1976;26(11):2084-9. [Pubmed]
Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [Pubmed]
Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [Pubmed]
Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. [Pubmed]
Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. [Pubmed]
Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. [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
  • Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)] Arzneimittelforschung. 1976;26(11):2084-9. Pubmed
  • Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. Pubmed
  • Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. Pubmed
  • Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. Pubmed
  • Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. Pubmed
  • Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. Pubmed
  • Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. Pubmed
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