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Identification
NameMirtazapine
Accession NumberDB00370  (APRD00685)
Typesmall molecule
Groupsapproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
6-AzamianserinNot AvailableIS
MepirzapineNot AvailableIS
MirtazapinGermanINN
MirtazapinaSpanishINN
MirtazapineNot AvailableBAN, USAN, DCF, BP 2011, Ph. Eur. 7, USP 34
MirtazapinumLatinINN
SaltsNot Available
Brand names
NameCompany
AvanzaSchering-Plough
AxitAlphapharm
Mirtabeneratiopharm
MirtazPinewood
MirtazonSchering-Plough
NorsetMSD France
PromyrtilSchering-Plough
RemergilMerck Sharp & Dohme
RemergonOrganon
RemeronSchering-Plough
Remeron SolTabNot Available
RexerSchering-Plough
ZispinOrganon
Brand mixturesNot Available
Categories
CAS number61337-67-5
WeightAverage: 265.3529
Monoisotopic: 265.157897623
Chemical FormulaC17H19N3
InChI KeyRONZAEMNMFQXRA-UHFFFAOYSA-N
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
IUPAC Name
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
SMILES
CN1CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperazinoazepines
SubclassNot Available
Direct parentPiperazinoazepines
Alternative parentsBenzazepines; Azepines; Piperazines; Benzene and Substituted Derivatives; Diazinanes; Pyridines and Derivatives; Tertiary Amines; Polyamines
Substituentsazepine; benzene; 1,4-diazinane; piperazine; pyridine; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the piperazinoazepines. These are compounds containing a piperazinoazepine skeleton, which consists of an azepie ring fused to a piperazine.
Pharmacology
IndicationFor the treatment of major depressive disorder.
PharmacodynamicsMirtazapine, 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.
Mechanism of actionMirtazapine acts as an antagonist at central pre-synaptic alpha(2)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(2)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT1 receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT1 receptors and as a potent antagonist at 5-HT2 (particularly subtypes 2A and 2C) and 5-HT3 receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H1-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.
AbsorptionRapid and complete, but, due to first-pass metabolism, absolute bioavailability is 50%.
Volume of distributionNot Available
Protein binding85%
Metabolism

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.

SubstrateEnzymesProduct
Mirtazapine
mirtazapine-N-oxideDetails
Mirtazapine
N-desmethylmirtazapineDetails
Mirtazapine
8-hydroxymirtazapineDetails
Route of eliminationThis drug is known to be substantially excreted by the kidney (75%).
Half life20-40 hours
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9873
Blood Brain Barrier + 0.9855
Caco-2 permeable + 0.7283
P-glycoprotein substrate Substrate 0.8462
P-glycoprotein inhibitor I Inhibitor 0.6148
P-glycoprotein inhibitor II Non-inhibitor 0.8975
Renal organic cation transporter Inhibitor 0.7956
CYP450 2C9 substrate Non-substrate 0.7988
CYP450 2D6 substrate Substrate 0.7894
CYP450 3A4 substrate Non-substrate 0.5148
CYP450 1A2 substrate Inhibitor 0.8503
CYP450 2C9 substrate Non-inhibitor 0.6675
CYP450 2D6 substrate Inhibitor 0.7222
CYP450 2C19 substrate Non-inhibitor 0.6206
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6031
Ames test Non AMES toxic 0.8079
Carcinogenicity Non-carcinogens 0.9742
Biodegradation Not ready biodegradable 0.9919
Rat acute toxicity 2.5197 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7532
hERG inhibition (predictor II) Inhibitor 0.7455
Pharmacoeconomics
Manufacturers
  • Actavis totowa llc
  • Aurobindo pharma ltd inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Organon usa inc
  • Actavis elizabeth llc
  • Alphapharm party ltd
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Sandoz inc
  • Watson laboratories inc florida
Packagers
Dosage forms
FormRouteStrength
TabletOral
Tablet, orally disintegratingOral
Prices
Unit descriptionCostUnit
Remeron SolTab 30 45 mg Dispersible Tablet Box114.4USDbox
Remeron SolTab 30 15 mg Dispersible Tablet Box107.58USDbox
Remeron SolTab 30 30 mg Dispersible Tablet Box107.27USDbox
Mirtazapine 30 45 mg Dispersible Tablet Box88.95USDbox
Mirtazapine 30 30 mg Dispersible Tablet Box83.48USDbox
Mirtazapine 30 15 mg Dispersible Tablet Box81.02USDbox
Remeron 45 mg tablet4.61USDtablet
Remeron 15 mg tablet4.42USDtablet
Remeron 45 mg soltab3.57USDtablet
Remeron 30 mg soltab3.55USDtablet
Remeron 30 mg tablet3.47USDtablet
Remeron 15 mg soltab3.26USDtablet
Mirtazapine 45 mg tablet2.91USDtablet
Mirtazapine 30 mg tablet2.85USDtablet
Mirtazapine 15 mg tablet2.77USDtablet
Mirtazapine 7.5 mg tablet2.56USDtablet
Apo-Mirtazapine 30 mg Tablet0.73USDtablet
Mylan-Mirtazapine 30 mg Tablet0.73USDtablet
Novo-Mirtazapine 30 mg Tablet0.73USDtablet
Phl-Mirtazapine 30 mg Tablet0.73USDtablet
Pms-Mirtazapine 30 mg Tablet0.73USDtablet
Ratio-Mirtazapine 30 mg Tablet0.73USDtablet
Sandoz Mirtazapine 30 mg Tablet0.73USDtablet
Pms-Mirtazapine 15 mg Tablet0.39USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States51788781993-01-122010-01-12
Canada23865472010-06-082020-10-09
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point114-116 °CNot Available
water solubilitySlightNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
water solubility1.10e+00 g/lALOGPS
logP2.9ALOGPS
logP3.21ChemAxon
logS-2.4ALOGPS
pKa (strongest basic)6.67ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area19.37ChemAxon
rotatable bond count0ChemAxon
refractivity82.66ChemAxon
polarizability30.35ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Leonid Metzger, “Methods for the preparation of mirtazapine intermediates.” U.S. Patent US20020165238, issued November 07, 2002.

US20020165238
General Reference
  1. 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
  2. Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed
  3. Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed
  4. Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed
  5. 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
  6. Pubmed
External Links
ResourceLink
KEGG DrugD00563
KEGG CompoundC07570
PubChem Compound4205
PubChem Substance46506965
ChemSpider4060
ChEBI6950
ChEMBLCHEMBL654
Therapeutic Targets DatabaseDAP000010
PharmGKBPA450522
Drug Product Database2256126
RxListhttp://www.rxlist.com/cgi/generic/mirtaz.htm
Drugs.comhttp://www.drugs.com/cdi/mirtazapine.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/rem1371.shtml
WikipediaMirtazapine
ATC CodesN06AX11
AHFS Codes
  • 28:16.04.92
PDB EntriesNot Available
FDA labelshow(904 KB)
MSDSshow(57.2 KB)
Interactions
Drug Interactions
Drug
ClonidinePossible hypertensive crisis
DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
DonepezilPossible antagonism of action
EthotoinThe hydantoins may reduce mirtazapine plasma concentrations and pharmacological effects
FluvoxamineFluvoxamine may increase the therapeutic and adverse effects of mirtazapine.
FosphenytoinThe hydantoins may reduce mirtazapine plasma concentrations and pharmacological effects
GalantaminePossible antagonism of action
IsocarboxazidPossible severe adverse reaction with this combination
MephenytoinThe hydantoins may reduce mirtazapine plasma concentrations and pharmacological effects
PhenelzinePossible severe adverse reaction with this combination
PhenytoinThe hydantoins may reduce mirtazapine plasma concentrations and pharmacological effects
RasagilinePossible severe adverse reaction with this combination
RivastigminePossible antagonism of action
TelithromycinTelithromycin may reduce clearance of Mirtazapine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Mirtazapine if Telithromycin is initiated, discontinued or dose changed.
TerbinafineTerbinafine may reduce the metabolism and clearance of Mirtazapine. Consider alternate therapy or monitor for therapeutic/adverse effects of Mirtazapine if Terbinafine is initiated, discontinued or dose changed.
TramadolIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Mirtazapine. These agents should not be administered within 14 days of each other.
TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TrimipramineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TriprolidineThe CNS depressants, Triprolidine and Mirtazapine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of mirtazapine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of mirtazapine if voriconazole is initiated, discontinued or dose changed.
ZolmitriptanUse of two serotonin modulators, such as zolmitriptan and mirtazapine, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

Targets

1. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

References:

  1. Westenberg HG: Pharmacology of antidepressants: selectivity or multiplicity? J Clin Psychiatry. 1999;60 Suppl 17:4-8; discussion 46-8. Pubmed
  2. Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed
  3. Nutt DJ: Care of depressed patients with anxiety symptoms. J Clin Psychiatry. 1999;60 Suppl 17:23-7; discussion 46-8. Pubmed
  4. Laakmann G, Schule C, Baghai T, Waldvogel E: Effects of mirtazapine on growth hormone, prolactin, and cortisol secretion in healthy male subjects. Psychoneuroendocrinology. 1999 Oct;24(7):769-84. Pubmed
  5. Waldinger MD, Berendsen HH, Schweitzer DH: Treatment of hot flushes with mirtazapine: four case reports. Maturitas. 2000 Oct 31;36(3):165-8. Pubmed
  6. Anttila SA, Leinonen EV: A review of the pharmacological and clinical profile of mirtazapine. CNS Drug Rev. 2001 Fall;7(3):249-64. Pubmed

2. 5-hydroxytryptamine receptor 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 3A P46098 Details

References:

  1. Westenberg HG: Pharmacology of antidepressants: selectivity or multiplicity? J Clin Psychiatry. 1999;60 Suppl 17:4-8; discussion 46-8. Pubmed
  2. Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed
  3. Kast RE, Foley KF: Cancer chemotherapy and cachexia: mirtazapine and olanzapine are 5-HT3 antagonists with good antinausea effects. Eur J Cancer Care (Engl). 2007 Jul;16(4):351-4. Pubmed
  4. de Boer T: The effects of mirtazapine on central noradrenergic and serotonergic neurotransmission. Int Clin Psychopharmacol. 1995 Dec;10 Suppl 4:19-23. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  6. Anttila SA, Leinonen EV: A review of the pharmacological and clinical profile of mirtazapine. CNS Drug Rev. 2001 Fall;7(3):249-64. Pubmed

3. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

References:

  1. Garcia-Sevilla JA, Ventayol P, Perez V, Rubovszky G, Puigdemont D, Ferrer-Alcon M, Andreoli A, Guimon J, Alvarez E: Regulation of platelet alpha 2A-adrenoceptors, Gi proteins and receptor kinases in major depression: effects of mirtazapine treatment. Neuropsychopharmacology. 2004 Mar;29(3):580-8. Pubmed
  2. Anttila SA, Leinonen EV: A review of the pharmacological and clinical profile of mirtazapine. CNS Drug Rev. 2001 Fall;7(3):249-64. Pubmed
  3. Besson A, Haddjeri N, Blier P, de Montigny C: Effects of the co-administration of mirtazapine and paroxetine on serotonergic neurotransmission in the rat brain. Eur Neuropsychopharmacol. 2000 May;10(3):177-88. Pubmed
  4. Schreiber S, Bleich A, Pick CG: Venlafaxine and mirtazapine: different mechanisms of antidepressant action, common opioid-mediated antinociceptive effects—a possible opioid involvement in severe depression? J Mol Neurosci. 2002 Feb-Apr;18(1-2):143-9. Pubmed
  5. Rogoz Z, Wrobel A, Dlaboga D, Maj J, Dziedzicka-Wasylewska M: Effect of repeated treatment with mirtazapine on the central alpha1-adrenergic receptors. J Physiol Pharmacol. 2002 Mar;53(1):105-16. Pubmed
  6. Rogoz Z, Wrobel A, Dlaboga D, Dziedzicka-Wasylewska M: Effect of repeated treatment with mirtazapine on the central dopaminergic D2/D3 receptors. Pol J Pharmacol. 2002 Jul-Aug;54(4):381-9. Pubmed

4. 5-hydroxytryptamine receptor 2C

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2C P28335 Details

References:

  1. Benelli A, Frigeri C, Bertolini A, Genedani S: Influence of mirtazapine on the sexual behavior of male rats. Psychopharmacology (Berl). 2004 Jan;171(3):250-8. Epub 2003 Nov 13. Pubmed
  2. Millan MJ, Gobert A, Rivet JM, Adhumeau-Auclair A, Cussac D, Newman-Tancredi A, Dekeyne A, Nicolas JP, Lejeune F: Mirtazapine enhances frontocortical dopaminergic and corticolimbic adrenergic, but not serotonergic, transmission by blockade of alpha2-adrenergic and serotonin2C receptors: a comparison with citalopram. Eur J Neurosci. 2000 Mar;12(3):1079-95. Pubmed
  3. Meert TF, Melis W, Aerts N, Clincke G: Antagonism of meta-chlorophenylpiperazine-induced inhibition of exploratory activity in an emergence procedure, the open field test, in rats. Behav Pharmacol. 1997 Aug;8(4):353-63. Pubmed
  4. Millan MJ: Serotonin 5-HT2C receptors as a target for the treatment of depressive and anxious states: focus on novel therapeutic strategies. Therapie. 2005 Sep-Oct;60(5):441-60. Pubmed
  5. Dekeyne A, Iob L, Millan MJ: Following long-term training with citalopram, both mirtazapine and mianserin block its discriminative stimulus properties in rats. Psychopharmacology (Berl). 2001 Jan;153(3):389-92. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

5. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Schreiber S, Rigai T, Katz Y, Pick CG: The antinociceptive effect of mirtazapine in mice is mediated through serotonergic, noradrenergic and opioid mechanisms. Brain Res Bull. 2002 Sep 30;58(6):601-5. Pubmed

6. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: no

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

7. Alpha-2C adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Alpha-2C adrenergic receptor P18825 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed
  3. Roth, BL; Driscol, J. “PDSD Ki Database”. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 2013-07-27.

8. 5-hydroxytryptamine receptor 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binding

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 7 P34969 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed
  3. Roth, BL; Driscol, J. “PDSD Ki Database”. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 2013-07-27.

9. Alpha-1 adrenergic receptor

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details
Alpha-1B adrenergic receptor P35368 Details
Alpha-1D adrenergic receptor P25100 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman’s The Pharmacological Basis of Therapeutics (in English) (12th ed.). New York: McGraw-Hill Professional. ISBN 978-0-07-162442-8.
  3. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed
  4. Wikstrom HV, Mensonides-Harsema MM, Cremers TI, Moltzen EK, Arnt J: Synthesis and pharmacological testing of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and its enantiomers in comparison with the two antidepressants mianserin and mirtazapine. J Med Chem. 2002 Jul 18;45(15):3280-5. Pubmed

10. D(2) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

References:

  1. Wikstrom HV, Mensonides-Harsema MM, Cremers TI, Moltzen EK, Arnt J: Synthesis and pharmacological testing of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and its enantiomers in comparison with the two antidepressants mianserin and mirtazapine. J Med Chem. 2002 Jul 18;45(15):3280-5. Pubmed
  2. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  3. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed

11. D(3) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D(3) dopamine receptor P35462 Details

References:

  1. Wikstrom HV, Mensonides-Harsema MM, Cremers TI, Moltzen EK, Arnt J: Synthesis and pharmacological testing of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and its enantiomers in comparison with the two antidepressants mianserin and mirtazapine. J Med Chem. 2002 Jul 18;45(15):3280-5. Pubmed
  2. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  3. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed

12. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. 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

13. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. 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

14. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. 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

15. 5-hydroxytryptamine receptor 2B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2B P41595 Details

References:

  1. de Boer T: The pharmacologic profile of mirtazapine. J Clin Psychiatry. 1996;57 Suppl 4:19-25. Pubmed
  2. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  3. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed
  4. Millan MJ, Gobert A, Rivet JM, Adhumeau-Auclair A, Cussac D, Newman-Tancredi A, Dekeyne A, Nicolas JP, Lejeune F: Mirtazapine enhances frontocortical dopaminergic and corticolimbic adrenergic, but not serotonergic, transmission by blockade of alpha2-adrenergic and serotonin2C receptors: a comparison with citalopram. Eur J Neurosci. 2000 Mar;12(3):1079-95. Pubmed

16. D(1) dopamine receptor

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details
D(1B) dopamine receptor P21918 Details

References:

  1. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  2. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed
  3. de Boer T: The effects of mirtazapine on central noradrenergic and serotonergic neurotransmission. Int Clin Psychopharmacol. 1995 Dec;10 Suppl 4:19-23. Pubmed
  4. Shaul Schreiber, Avi Bleich, and Chaim G. Pick. Venlafaxine and Mirtazapine. Journal of Molecular Neuroscience. 2002(18) 143-149

17. Histamine H3 receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Histamine H3 receptor Q9Y5N1 Details

References:

  1. Pytliak M, Vargova V, Mechirova V, Felsoci M: Serotonin receptors – from molecular biology to clinical applications. Physiol Res. 2011;60(1):15-25. Epub 2010 Oct 15. Pubmed
  2. Fernandez J, Alonso JM, Andres JI, Cid JM, Diaz A, Iturrino L, Gil P, Megens A, Sipido VK, Trabanco AA: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. J Med Chem. 2005 Mar 24;48(6):1709-12. Pubmed
  3. de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM: Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers. Neuropharmacology. 1988 Apr;27(4):399-408. Pubmed
  4. Millan MJ, Gobert A, Rivet JM, Adhumeau-Auclair A, Cussac D, Newman-Tancredi A, Dekeyne A, Nicolas JP, Lejeune F: Mirtazapine enhances frontocortical dopaminergic and corticolimbic adrenergic, but not serotonergic, transmission by blockade of alpha2-adrenergic and serotonin2C receptors: a comparison with citalopram. Eur J Neurosci. 2000 Mar;12(3):1079-95. Pubmed

18. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. Millan MJ, Gobert A, Rivet JM, Adhumeau-Auclair A, Cussac D, Newman-Tancredi A, Dekeyne A, Nicolas JP, Lejeune F: Mirtazapine enhances frontocortical dopaminergic and corticolimbic adrenergic, but not serotonergic, transmission by blockade of alpha2-adrenergic and serotonin2C receptors: a comparison with citalopram. Eur J Neurosci. 2000 Mar;12(3):1079-95. Pubmed

19. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

References:

  1. Millan MJ, Gobert A, Rivet JM, Adhumeau-Auclair A, Cussac D, Newman-Tancredi A, Dekeyne A, Nicolas JP, Lejeune F: Mirtazapine enhances frontocortical dopaminergic and corticolimbic adrenergic, but not serotonergic, transmission by blockade of alpha2-adrenergic and serotonin2C receptors: a comparison with citalopram. Eur J Neurosci. 2000 Mar;12(3):1079-95. Pubmed

20. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. Millan MJ, Gobert A, Rivet JM, Adhumeau-Auclair A, Cussac D, Newman-Tancredi A, Dekeyne A, Nicolas JP, Lejeune F: Mirtazapine enhances frontocortical dopaminergic and corticolimbic adrenergic, but not serotonergic, transmission by blockade of alpha2-adrenergic and serotonin2C receptors: a comparison with citalopram. Eur J Neurosci. 2000 Mar;12(3):1079-95. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Anttila SA, Leinonen EV: A review of the pharmacological and clinical profile of mirtazapine. CNS Drug Rev. 2001 Fall;7(3):249-64. Pubmed
  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. Epub 2009 Nov 24. Pubmed
  3. Stormer E, von Moltke LL, Shader RI, Greenblatt DJ: Metabolism of the antidepressant mirtazapine in vitro: contribution of cytochromes P-450 1A2, 2D6, and 3A4. Drug Metab Dispos. 2000 Oct;28(10):1168-75. Pubmed

2. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Anttila SA, Leinonen EV: A review of the pharmacological and clinical profile of mirtazapine. CNS Drug Rev. 2001 Fall;7(3):249-64. Pubmed
  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. Epub 2009 Nov 24. Pubmed
  3. Stormer E, von Moltke LL, Shader RI, Greenblatt DJ: Metabolism of the antidepressant mirtazapine in vitro: contribution of cytochromes P-450 1A2, 2D6, and 3A4. Drug Metab Dispos. 2000 Oct;28(10):1168-75. Pubmed

3. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Anttila SA, Leinonen EV: A review of the pharmacological and clinical profile of mirtazapine. CNS Drug Rev. 2001 Fall;7(3):249-64. Pubmed
  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. Epub 2009 Nov 24. Pubmed
  3. Stormer E, von Moltke LL, Shader RI, Greenblatt DJ: Metabolism of the antidepressant mirtazapine in vitro: contribution of cytochromes P-450 1A2, 2D6, and 3A4. Drug Metab Dispos. 2000 Oct;28(10):1168-75. Pubmed

4. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 19, 2014 10:09