CAS 61337-67-5|CAS 85650-52-8|CAS 61337-87-9|Remeron|Avanza|Mirtazapine|5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene|5-methyl-2,5,19-triazatetracy...

基本信息

化学结构

分子式

C₁₇H₁₉N₃

分子量

265.35286

精确质量

265.15789762

电荷

InChI

InChI=1S/C17H19N3/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20/h2-8,16H,9-12H2,1H3

InChIKey

RONZAEMNMFQXRA-UHFFFAOYSA-N

Canonic Smiles

CN1CCN2C(C1)c1ccccc1Cc1c2nccc1

Isomeric Smiles

N12C(CN(CC1)C)c1c(Cc3c2nccc3)cccc1

计算属性

JChem

LogD (pH = 7.4)

3.13

LogD (pH = 5.5)

1.82

Log P

3.21

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

6.67

极化表面积

19.37

极化性

30.34

摩尔折射率

82.66

LOG S

-2.51

数据来源

名称和标识

别名

AvanzaMirtazapineRemeronOrg 3770Esmirtazapine6-AzamianserinMirtazapine1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepineOrg-3770ZispinMepirzepineMirtazapine [Usan:Ban:Inn]MirtazepineMirtazapinum [INN-Latin]mirtazapineMirtazapina [INN-Spanish]5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaenemirtazapine1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepineMirtazapine

IUPAC传统名

5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene mirtazapine 5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8(13),9,11,15,17-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8,10,12,15,17-hexaene

IUPAC标准名

5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8(13),9,11,16,18-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8(13),9,11,15,17-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8(13),9,11,15,17-hexaene

商标名

Remeron, Avanza, ZispinZispinRemeronMirtabeneMirtazRemergilRemeron SoltabAxitMirtazonRemergonPromyrtilNorsetRexerAvanza

API名称

Mirtazapine

国际非专利药品(INN)

mirtazapinemirtazapinummirtazapina

名称和标识

数据登录号

CAS号

61337-67-585650-52-861337-87-9

PubChem CID

42056451144

PubChem SID

160963717465069652472453156394976

MDL号

MFCD00865427

维基百科标题

EsmirtazapineMirtazapine

Chemspider ID

DrugBank ID

CHEMBL

Medline Plus

美国药典/FDA物质标识码

ATC码

CHEBI ID

KEGG ID

专利号

US2007190043US2006258715WO2006008302WO2007095606WO2008141057EP1225174EP1658850US2007185084WO2007109289EP1990639US2003096805EP1879027US2007207222US2008214613

Beilstein号

549345

MetaboLights数据库

MTBLS4967MTBLS2291MTBLS1693MTBLS407

PubMed文献链接

33856954338414033355990033685359104467351065321833163376169652091854882733422759

ACToR数据库

85650-52-861337-67-5

BRENDA Ligand数据库

210369

BKMS React数据库

210369

Drug Central Database

SureChEMBL数据库

LINCS数据库

VSDB Database

BRENDA数据库

KEGG DRUG Database

CompTox数据库

BindingDB数据库

数据登录号

化合物性质

产品相关信息

安全信息

保存条件

-20°C

-20°C Freezer

MSDS下载

下载链接

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

德国WGK号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子相关蛋白质

分子图谱

描述信息

DrugBank

DB00370

Drug Groups

approved

Description

Mirtazapine is an antidepressant introduced by Organon International in 1996 used for the treatment of moderate to severe depression. Mirtazapine has a tetracyclic chemical structure and is classified as a noradrenergic and specific serotonergic antidepressant (NaSSA). It is the only tetracyclic antidepressant that has been approved by the Food and Drug Administration to treat depression. [Wikipedia]

Indication

For the treatment of major depressive disorder.

Pharmacology

Mirtazapine, an antidepressant of the piperazinoazepine class, is a tetracyclic compound with an anxiolytic effect. Mirtazapine has fewer ADRs than tricyclic antidepressants and is better tolerated. Selective blockade of specific serotonin receptors by mirtazapine likey minimizes side effects typical of other antidepressants.

Toxicity

Symptoms of overdose include disorientation, drowsiness, impaired memory, and tachycardia. LD50 is 600-720mg/kg (oral, mice) and 320-490mg/kg (oral, rat) [PMID: 10333982]

Affected Organisms

Humans and other mammals

Biotransformation

Mirtazapine is extensively metabolized by demethylation and hydroxylation followed by glucuronide conjugation. Cytochrome P450 2D6 and cytochrome P450 1A2 are involved in formation of the 8-hydroxy metabolite of mirtazapine, and cytochrome P450 3A4 is responsible for the formation of the N-desmethyl and N-oxide metabolites. Several metabolites possess pharmacological activity, but plasma levels are very low.

Absorption

Rapid and complete, but, due to first-pass metabolism, absolute bioavailability is 50%.

Half Life

20-40 hours

Protein Binding

85%

Elimination

This drug is known to be substantially excreted by the kidney (75%).

References

• Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. [Pubmed]

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. [Pubmed]

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. [Pubmed]

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. [Pubmed]

• Baldwin DS, Anderson IM, Nutt DJ, Bandelow B, Bond A, Davidson JR, den Boer JA, Fineberg NA, Knapp M, Scott J, Wittchen HU: Evidence-based guidelines for the pharmacological treatment of anxiety disorders: recommendations from the British Association for Psychopharmacology. J Psychopharmacol. 2005 Nov;19(6):567-96. [Pubmed]

• [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2016

Research Area: Neurological Disease
Biological Activity:
Mirtazapine (Remeron, Avanza) is a potent tetracyclic antidepressant. Mirtazapine (Remeron, Avanza) used primarily in the treatment of depression. It is also sometimes used as a hypnotic, antiemetic, and appetite stimulant, and for the treatment of anxiety, among other indications. In addition, along with its close analogues mianserin and setiptiline, mirtazapine (Remeron, Avanza) is one of the few noradrenergic and specific serotonergic antidepressants (NaSSAs). Additionally, the (S)-(+)-enantiomer of mirtazapine, which is also called esmirtazapine, is currently under development for the treatment of insomnia and menopausal symptoms. Mirtazapine’s primary use is the treatment of major depressive disorder. Mirtazapine (Remeron, Avanza) has been found to be useful in the treatment of many diseases, including generalized anxiety disorder, social anxiety disorder, obsessive-compulsive disorder, panic disorder, post-traumatic stress disorder, seasonal affective disorder, insomnia, nausea and vomiting, diminished appetite and associated weight loss, and itching as well. [1]References on Mirtazapine (Remeron, Avanza)[1] http://en.wikipedia.org/wiki/Mirtazapine, ,

M0443

Biochem/physiol Actions
Mirtazapine is a noradrenergic and specific serotonergic antidepressant (NaSSA). Mirtazapine agonizes selective adrenergic and serotonergic receptors so that both NE release and 5-HT1A mediated serotonergic signaling are increased.

TRC

M365000

An α2-Adrenergic blocker; analogue of Mianserin. Antidepressant.

描述信息

参考文献

PubChem文献

数据源提供

• Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. Pubmed

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed

• Pubmed

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed

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

• De Boer, T., et al.: Neuropharmacology, 27, 399 (1988)

• Smith, W.T., et al.: Psychopharmacol. Bull., 26, 191 (1990)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

IUPAC标准名

商标名

Remeron, Avanza, ZispinZispinRemeronMirtabeneMirtazRemergilRemeron SoltabAxitMirtazonRemergonPromyrtilNorsetRexerAvanza

API名称

Mirtazapine

国际非专利药品(INN)

mirtazapinemirtazapinummirtazapina

化合物性质

产品相关信息

安全信息

保存条件

-20°C

-20°C Freezer

MSDS下载

下载链接

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

德国WGK号

参考文献

PubChem文献

数据源提供

• Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. Pubmed

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed

• Pubmed

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed

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

• De Boer, T., et al.: Neuropharmacology, 27, 399 (1988)

• Smith, W.T., et al.: Psychopharmacol. Bull., 26, 191 (1990)

生物活性

PubChem BioAssay

描述信息

DrugBank

DB00370

Drug Groups

approved

Description

Indication

For the treatment of major depressive disorder.

Pharmacology

Toxicity

Symptoms of overdose include disorientation, drowsiness, impaired memory, and tachycardia. LD50 is 600-720mg/kg (oral, mice) and 320-490mg/kg (oral, rat) [PMID: 10333982]

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Rapid and complete, but, due to first-pass metabolism, absolute bioavailability is 50%.

Half Life

20-40 hours

Protein Binding

85%

Elimination

This drug is known to be substantially excreted by the kidney (75%).

References

• Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. [Pubmed]

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. [Pubmed]

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. [Pubmed]

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. [Pubmed]

• [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2016

Wikipedia

Esmirtazapine