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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015620
Secondary Accession Numbers
  • HMDB15620
Metabolite Identification
Common NameMianserin
DescriptionMianserin is only found in individuals that have used or taken this drug. It is a tetracyclic compound with antidepressant effects. Mianserin was previously available internationally, however in most markets it has been phased out in favor of Mirtazapine.Mianserin's mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.
Structure
Data?1582753317
Synonyms
ValueSource
1,2,3,4,10,14b-Hexahydro-2-methyldibenzo(c,F)pyrazino(1,2-a)azepineChEBI
MianserinaChEBI
MianserineChEBI
MianserinumChEBI
TolvonKegg
Hydrochloride, mianserinMeSH, HMDB
Mianserin hydrochlorideMeSH, HMDB
Mianserin monohydrochlorideMeSH, HMDB
LerivonMeSH, HMDB
Monohydrochloride, mianserinMeSH, HMDB
Org GB 94MeSH, HMDB
Chemical FormulaC18H20N2
Average Molecular Weight264.3648
Monoisotopic Molecular Weight264.16264865
IUPAC Name5-methyl-2,5-diazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaene
Traditional Namemianserin
CAS Registry Number24219-97-4
SMILES
CN1CCN2C(C1)C1=CC=CC=C1CC1=CC=CC=C21
InChI Identifier
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
InChI KeyUEQUQVLFIPOEMF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Piperazino-azepine
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Aralkylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Azepine
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM164.530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP3.52ALOGPS
logP3.83ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)6.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.5 m³·mol⁻¹ChemAxon
Polarizability30.76 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.64731661259
DarkChem[M-H]-159.75631661259
DeepCCS[M-2H]-189.94330932474
DeepCCS[M+Na]+165.50730932474
AllCCS[M+H]+162.732859911
AllCCS[M+H-H2O]+158.932859911
AllCCS[M+NH4]+166.232859911
AllCCS[M+Na]+167.332859911
AllCCS[M-H]-172.032859911
AllCCS[M+Na-2H]-171.232859911
AllCCS[M+HCOO]-170.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MianserinCN1CCN2C(C1)C1=CC=CC=C1CC1=CC=CC=C213313.3Standard polar33892256
MianserinCN1CCN2C(C1)C1=CC=CC=C1CC1=CC=CC=C212209.5Standard non polar33892256
MianserinCN1CCN2C(C1)C1=CC=CC=C1CC1=CC=CC=C212186.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mianserin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0075-0390000000-5eafc66a2a866ea518a22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mianserin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mianserin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-014i-0090000000-49135d3660182f98e5f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-014i-0090000000-49da9cd1f48c7c59b19c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-0aor-4390000000-a6944a5b23139d1843752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-0a4i-8960000000-91b2a10929bb6f8a03e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-0a4l-6920000000-c2fd706d219cb46dce7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-0aou-6910000000-21ad202872a2bb0e46442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-014l-7910000000-e01badcead1453e1b2022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-014l-8900000000-a181ec3c5cb717213c412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin LC-ESI-QFT , positive-QTOFsplash10-014i-9700000000-0617c8ac60e03f3e07842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin 15V, Positive-QTOFsplash10-014i-0090000000-ba7681c79fe8a4ba59e92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin 90V, Positive-QTOFsplash10-0aou-6910000000-e167a1117afd08c6d78e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin 75V, Positive-QTOFsplash10-0a4l-6920000000-08891cd9dd3563a685752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin 30V, Positive-QTOFsplash10-014i-0090000000-c5f5381432dcb2616e732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin 45V, Positive-QTOFsplash10-0aor-4290000000-fb01e091e2313afb98a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mianserin 60V, Positive-QTOFsplash10-0a4i-9870000000-1fa149bdec9236f361342021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 10V, Positive-QTOFsplash10-014i-0090000000-7b78167a8e187b0dfb5b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 20V, Positive-QTOFsplash10-014i-0090000000-04c8704effb3cd1ff4ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 40V, Positive-QTOFsplash10-0006-7980000000-8a47c05b188d9c4da8972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 10V, Negative-QTOFsplash10-03di-0090000000-18e557221e4d4865372a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 20V, Negative-QTOFsplash10-03di-0090000000-45c02349685bee4628f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 40V, Negative-QTOFsplash10-0006-0910000000-9be5a0a92940f55d1f2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 10V, Positive-QTOFsplash10-014i-0090000000-36c7dd6f4d455ec0c23e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 20V, Positive-QTOFsplash10-014i-0090000000-ced1477b0d8b3266fd9d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 40V, Positive-QTOFsplash10-052f-7980000000-3fb1aa0f8693c196c7dc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mianserin 10V, Negative-QTOFsplash10-03di-0090000000-81ccc7ccef803f104ccb2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06148 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06148 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4040
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMianserin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID51137
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:8627567 ]
  2. 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:8764331 ]
  3. 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:9232538 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report]. Lakartidningen. 2002 Jun 20;99(25):2854-6. [PubMed:12143142 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Rojdmark S, von Bahr C: [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report]. Lakartidningen. 2002 Jun 20;99(25):2854-6. [PubMed:12143142 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Dekeyne A, Millan MJ: Discriminative stimulus properties of the selective and highly potent alpha2-adrenoceptor agonist, S18616, in rats: mediation by the alpha2A subtype, and blockade by the atypical antidepressants, mirtazapine and mianserin. Neuropharmacology. 2006 Sep;51(4):718-26. Epub 2006 Jun 30. [PubMed:16814817 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Grinshpoon A, Valevski A, Moskowitz M, Weizman A: Beneficial effect of the addition of the 5-HT 2A/2C and alpha2 antagonist mianserin to ongoing haloperidol treatment in drug-resistant chronically hospitalized schizophrenic patients. Eur Psychiatry. 2000 Sep;15(6):388-90. [PubMed:11004734 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular weight:
51820.7
References
  1. Grinshpoon A, Valevski A, Moskowitz M, Weizman A: Beneficial effect of the addition of the 5-HT 2A/2C and alpha2 antagonist mianserin to ongoing haloperidol treatment in drug-resistant chronically hospitalized schizophrenic patients. Eur Psychiatry. 2000 Sep;15(6):388-90. [PubMed:11004734 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Csaba G, Kovacs P, Pallinger E: Prolonged effect of the tricyclic antidepressant, mianserin on the serotonin and histamine content of young rats' white blood cells and mast cells. A case of late-imprinting. Pharmacol Res. 2003 Nov;48(5):457-60. [PubMed:12967590 ]
  2. Grinshpoon A, Valevski A, Moskowitz M, Weizman A: Beneficial effect of the addition of the 5-HT 2A/2C and alpha2 antagonist mianserin to ongoing haloperidol treatment in drug-resistant chronically hospitalized schizophrenic patients. Eur Psychiatry. 2000 Sep;15(6):388-90. [PubMed:11004734 ]
  3. Nowak JZ, Arrang JM, Schwartz JC, Garbarg M: Interaction between mianserin, an antidepressant drug, and central H1- and H2-histamine-receptors: in vitro and in vivo studies and radioreceptor assay. Neuropharmacology. 1983 Mar;22(3):259-66. [PubMed:6302549 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]