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

• ChemBase ID: 4416
• Molecular Formular: C18H20N2
• Molecular Mass: 264.3648
• Monoisotopic Mass: 264.16264865
• SMILES: N12C(CN(CC1)C)c1c(Cc3c2cccc3)cccc1
• Canonical SMILES: CN1CCN2C(C1)c1ccccc1Cc1c2cccc1
• 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

NAMES AND DATABASE IDS

Names

• 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
• 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
• Brand Name: Bolvidon; Norval; Tolvan
• Synonyms: Mianseryna [polish]; Mianserinum [inn-latin]; Mianserine [inn-french]; Mianserina [inn-spanish]; Mianserine; Mianserin

Database IDs

• CAS Number: 24219-97-4
• PubChem SID: 46508096; 160967848
• PubChem CID: 4184

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.3987954
• LogD (pH = 7.4): 3.7070787
• Log P: 3.8311977
• Molar Refractivity: 84.4987 cm^3
• Polarizability: 32.159184 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.52
• LOG S: -3.06
• Solubility (Water): 2.32e-01 g/l

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

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