CAS 24219-97-4|Mianseryna [polish]|Bolvidon|Norval|Mianserina [inn-spanish]|Mianserin|Mianserine [inn-french]|Mianserine|Mianserinum [inn-latin]|5-methyl-2,5-diazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]...

General Information

Structure

Molecular Formula

C₁₈H₂₀N₂

Molecular Mass

264.3648

Exact Mass

264.16264865

Charge

0

InChI

InChI=1S/C18H20N2/c1-19-10-11-20-17-9-5-3-7-15(17)12-14-6-2-4-8-16(14)18(20)13-19/h2-9,18H,10-13H2,1H3

InChIKey

UEQUQVLFIPOEMF-UHFFFAOYSA-N

Canonic Smiles

CN1CCN2C(C1)c1ccccc1Cc1c2cccc1

Isomeric Smiles

N12C(CN(CC1)C)c1c(Cc3c2cccc3)cccc1

Calculated Properties

JChem

LogD (pH = 7.4)

3.71

LogD (pH = 5.5)

2.40

Log P

3.83

Rotatable Bonds

0

H Donor

0

H Acceptors

2

Lipinski's Rule of Five

true

Acid pKa

6.92

Polar Surface Area

6.48

Polarizability

30.50

Molar Refractivity

84.50

LOG S

-3.13

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Mianseryna [polish]Mianserina [inn-spanish]MianserinMianserine [inn-french]MianserineMianserinum [inn-latin]mianserin1,2,3,4,10,14b-Hexahydro-2-methyldibenzo(c,f)pyrazino(1,2-a)azepine

Brand Name

BolvidonNorvalTolvan

IUPAC name

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

IUPAC Traditional name

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

International Nonproprietary Name (INN)

mianserinmianserinemianserinamianserinum

Names and Identifiers

Registration numbers

PubChem SID

1609678484650809656464297

PubChem CID

CAS Number

CHEBI ID

LINCS Database

BindingDB Database

BRENDA Database

3.6.5.53.4.21.262.4.1.17

BRENDA Ligand Database

16777575636

UniProt Database

O77408P18089O01670P22270Q25321P08913

PubMed Citation Links

1803329720825390

Drug Central Database

CHEMBL

SureChEMBL Database

Beilstein Number

MetaboLights Database

ACToR Database

BKMS React Database

DrugBank ID

CompTox Database

Wikipedia Title

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB06148

Drug Groups

approved

Description

A tetracyclic compound with antidepressant effects. Mianserin was previously available internationally, however in most markets it has been phased out in favor of Mirtazapine.

Indication

For the treatment of depression.

Pharmacology

Mianserin is a tetracyclic antidepressant that has antihistaminic and hypnosedative, but almost no anticholinergic, effect. It is a weak inhibitor of norepinephrine reuptake and strongly stimulates the release of norepinephrine. Interactions with serotonin receptors in the central nervous system have also been found. Its effect is usually noticeable after one to three weeks. Mianserin may cause drowsiness and hematological problems.

Toxicity

Oral rat LD₅₀: 780mg/kg

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

Absorbed following oral administration.

Half Life

10-17 hours

Protein Binding

90%

References

• Koyama E, Chiba K, Tani M, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the stereoselective metabolism of mianserin enantiomers. J Pharmacol Exp Ther. 1996 Jul;278(1):21-30. [Pubmed]

• de Boer TH, Nefkens F, van Helvoirt A, van Delft AM: Differences in modulation of noradrenergic and serotonergic transmission by the alpha-2 adrenoceptor antagonists, mirtazapine, mianserin and idazoxan. J Pharmacol Exp Ther. 1996 May;277(2):852-60. [Pubmed]

• Kelder J, Funke C, De Boer T, Delbressine L, Leysen D, Nickolson V: A comparison of the physicochemical and biological properties of mirtazapine and mianserin. J Pharm Pharmacol. 1997 Apr;49(4):403-11. [Pubmed]

External Links

• [Wikipedia]

ChEBI

CHEBI:51137

A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.

Molecule Details

References

PubChem Literature

From Data Sources

• Kelder J, Funke C, De Boer T, Delbressine L, Leysen D, Nickolson V: A comparison of the physicochemical and biological properties of mirtazapine and mianserin. J Pharm Pharmacol. 1997 Apr;49(4):403-11. Pubmed

• Koyama E, Chiba K, Tani M, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the stereoselective metabolism of mianserin enantiomers. J Pharmacol Exp Ther. 1996 Jul;278(1):21-30. Pubmed

• de Boer TH, Nefkens F, van Helvoirt A, van Delft AM: Differences in modulation of noradrenergic and serotonergic transmission by the alpha-2 adrenoceptor antagonists, mirtazapine, mianserin and idazoxan. J Pharmacol Exp Ther. 1996 May;277(2):852-60. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:4416