Esmirtazapine

Identification

Name
Esmirtazapine
Accession Number
DB06678
Type
Small Molecule
Groups
Investigational
Description

Esmirtazapine (SCH 900265) is a drug which was under development by Organon for the treatment of insomnia and vasomotor symptoms (e.g., hot flashes) associated with menopause. Esmirtazapine is the (S)-(+)-enantiomer of mirtazapine and possesses similar overall pharmacology, including inverse agonist actions at H1 and 5-HT2 receptors and antagonist actions at α2-adrenergic receptors. Merck has terminated its internal clinical development program for esmirtazapine as of March 2010.

Structure
Thumb
Synonyms
  • (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
External IDs
ORG-44-20 / ORG-4420 / ORG-50,081 / SCH 900265
Product Ingredients
IngredientUNIICASInChI Key
Esmirtazapine hydrochlorideJ12BQ47O1N 1448014-35-4SISMRXGXKXMBKT-PKLMIRHRSA-N
Esmirtazapine maleateI2U18E6JKA 680993-85-5RPUBHMMISKEXSR-MLCLTIQSSA-N
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
4685R51V7M
CAS number
61337-87-9
Weight
Average: 265.36
Monoisotopic: 265.157897624
Chemical Formula
C17H19N3
InChI Key
RONZAEMNMFQXRA-MRXNPFEDSA-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/t16-/m1/s1
IUPAC Name
(7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene
SMILES
[H][C@]12CN(C)CCN1C1=C(CC3=CC=CC=C23)C=CC=N1

Pharmacology

Indication

Investigated for use/treatment in insomnia and sleep disorders.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHistamine H1 receptor
inverse agonist
Human
U5-hydroxytryptamine receptor 2
inverse agonist
Human
UAlpha-2 adrenergic receptors
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

10 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Esmirtazapine can be increased when it is combined with 1,10-Phenanthroline.Experimental
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Esmirtazapine.Experimental, Illicit
3,4-DichloroisocoumarinThe serum concentration of Esmirtazapine can be increased when it is combined with 3,4-Dichloroisocoumarin.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Esmirtazapine.Experimental, Illicit
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Esmirtazapine.Experimental, Illicit
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Esmirtazapine can be increased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Esmirtazapine.Experimental, Illicit
4-MethoxyamphetamineEsmirtazapine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the serotonergic activities of Esmirtazapine.Experimental
AbirateroneThe serum concentration of Esmirtazapine can be increased when it is combined with Abiraterone.Approved
AcenocoumarolEsmirtazapine may increase the anticoagulant activities of Acenocoumarol.Approved
AgmatineEsmirtazapine may decrease the antihypertensive activities of Agmatine.Experimental, Investigational
AlogliptinThe serum concentration of Esmirtazapine can be increased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Esmirtazapine can be increased when it is combined with Alpha-1-proteinase inhibitor.Approved
AltretamineAltretamine may increase the orthostatic hypotensive activities of Esmirtazapine.Approved
AmiodaroneThe metabolism of Esmirtazapine can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe metabolism of Esmirtazapine can be increased when combined with Amobarbital.Approved, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Esmirtazapine.Approved, Illicit
AmprenavirThe serum concentration of Esmirtazapine can be increased when it is combined with Amprenavir.Approved
Antithrombin III humanThe serum concentration of Esmirtazapine can be increased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Esmirtazapine can be increased when it is combined with Apixaban.Approved
ApomorphineEsmirtazapine may decrease the antihypertensive activities of Apomorphine.Approved, Investigational
ApraclonidineEsmirtazapine may decrease the antihypertensive activities of Apraclonidine.Approved
AprotininThe serum concentration of Esmirtazapine can be increased when it is combined with Aprotinin.Approved, Withdrawn
ArbutamineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Arbutamine.Approved
ArformoterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Arformoterol.Approved, Investigational
ArgatrobanThe serum concentration of Esmirtazapine can be increased when it is combined with Argatroban.Approved, Investigational
ArtemetherThe metabolism of Esmirtazapine can be decreased when combined with Artemether.Approved
AsunaprevirThe serum concentration of Esmirtazapine can be increased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Esmirtazapine can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Esmirtazapine can be decreased when combined with Atomoxetine.Approved
BambuterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Bambuterol.Approved
BarbexacloneThe metabolism of Esmirtazapine can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Esmirtazapine can be increased when combined with Barbital.Illicit
BatimastatThe serum concentration of Esmirtazapine can be increased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Esmirtazapine can be increased when it is combined with Benazepril.Approved, Investigational
BenmoxinBenmoxin may increase the serotonergic activities of Esmirtazapine.Withdrawn
BenzamidineThe serum concentration of Esmirtazapine can be increased when it is combined with Benzamidine.Experimental
BenzphetamineEsmirtazapine may decrease the antihypertensive activities of Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineEsmirtazapine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Esmirtazapine.Approved
BetaxololThe metabolism of Esmirtazapine can be decreased when combined with Betaxolol.Approved
BethanidineEsmirtazapine may decrease the antihypertensive activities of Bethanidine.Approved
BivalirudinThe serum concentration of Esmirtazapine can be increased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Esmirtazapine can be increased when it is combined with Boceprevir.Withdrawn
BrimonidineEsmirtazapine may decrease the antihypertensive activities of Brimonidine.Approved
BrimonidineThe therapeutic efficacy of Brimonidine can be decreased when used in combination with Esmirtazapine.Approved
BromocriptineEsmirtazapine may decrease the antihypertensive activities of Bromocriptine.Approved, Investigational
BupropionThe metabolism of Esmirtazapine can be decreased when combined with Bupropion.Approved
CandoxatrilThe serum concentration of Esmirtazapine can be increased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Esmirtazapine can be increased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Esmirtazapine can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Esmirtazapine can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneCaroxazone may increase the serotonergic activities of Esmirtazapine.Withdrawn
CelecoxibThe metabolism of Esmirtazapine can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Celiprolol.Approved, Investigational
ChloroquineThe metabolism of Esmirtazapine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Esmirtazapine.Illicit, Withdrawn
ChlorpromazineThe metabolism of Esmirtazapine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Esmirtazapine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
ChymostatinThe serum concentration of Esmirtazapine can be increased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Esmirtazapine can be increased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Esmirtazapine can be increased when it is combined with Cilazapril.Approved
CimetidineThe metabolism of Esmirtazapine can be decreased when combined with Cimetidine.Approved
CinacalcetThe serum concentration of Esmirtazapine can be increased when it is combined with Cinacalcet.Approved
CirazolineEsmirtazapine may increase the vasopressor activities of Cirazoline.Experimental
CitalopramThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Citalopram.Approved
ClemastineThe metabolism of Esmirtazapine can be decreased when combined with Clemastine.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Clenbuterol.Approved, Vet Approved
ClobazamThe metabolism of Esmirtazapine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Esmirtazapine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClonidineEsmirtazapine may decrease the antihypertensive activities of Clonidine.Approved
ClotrimazoleThe metabolism of Esmirtazapine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Esmirtazapine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Esmirtazapine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Esmirtazapine can be decreased when combined with Cocaine.Approved, Illicit
Dabigatran etexilateThe serum concentration of Esmirtazapine can be increased when it is combined with Dabigatran etexilate.Approved
DarexabanThe serum concentration of Esmirtazapine can be increased when it is combined with Ym150.Investigational
DarifenacinThe metabolism of Esmirtazapine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Esmirtazapine can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Esmirtazapine can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Esmirtazapine can be decreased when combined with Desipramine.Approved
DesmopressinThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Desmopressin.Approved
DexmedetomidineEsmirtazapine may decrease the antihypertensive activities of Dexmedetomidine.Approved, Vet Approved
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Esmirtazapine.Approved
DextroamphetamineDextroamphetamine may decrease the sedative activities of Esmirtazapine.Approved, Illicit
DicoumarolEsmirtazapine may increase the anticoagulant activities of Dicoumarol.Approved
DiethylpropionDiethylpropion may decrease the sedative activities of Esmirtazapine.Approved, Illicit
DihydroergotamineEsmirtazapine may decrease the antihypertensive activities of Dihydroergotamine.Approved
DiphenhydramineThe metabolism of Esmirtazapine can be decreased when combined with Diphenhydramine.Approved
DipivefrinEsmirtazapine may decrease the antihypertensive activities of Dipivefrin.Approved
DobutamineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Dobutamine.Approved
DronedaroneThe metabolism of Esmirtazapine can be decreased when combined with Dronedarone.Approved
DroxidopaEsmirtazapine may decrease the antihypertensive activities of Droxidopa.Approved, Investigational
DuloxetineDuloxetine may increase the serotonergic activities of Esmirtazapine.Approved
EcabetThe serum concentration of Esmirtazapine can be increased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Esmirtazapine can be increased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Esmirtazapine can be increased when it is combined with Elafin.Investigational
EliglustatThe metabolism of Esmirtazapine can be decreased when combined with Eliglustat.Approved
EnalaprilThe serum concentration of Esmirtazapine can be increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Esmirtazapine can be increased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Esmirtazapine can be increased when it is combined with Enalkiren.Experimental
EphedraEsmirtazapine may decrease the antihypertensive activities of Ephedra.Approved, Nutraceutical, Withdrawn
EpinephrineEsmirtazapine may decrease the antihypertensive activities of Epinephrine.Approved, Vet Approved
ErgotamineEsmirtazapine may decrease the antihypertensive activities of Ergotamine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Escitalopram.Approved, Investigational
Ethyl biscoumacetateEsmirtazapine may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtomidateEsmirtazapine may decrease the antihypertensive activities of Etomidate.Approved
FaldaprevirThe serum concentration of Esmirtazapine can be increased when it is combined with Bi201335.Investigational
FenoterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Fenoterol.Approved
FluindioneEsmirtazapine may increase the anticoagulant activities of Fluindione.Investigational
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Esmirtazapine.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Esmirtazapine.Approved, Investigational
FormoterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Formoterol.Approved, Investigational
FosamprenavirThe serum concentration of Esmirtazapine can be increased when it is combined with Fosamprenavir.Approved
FosinoprilThe serum concentration of Esmirtazapine can be increased when it is combined with Fosinopril.Approved
FurazolidoneFurazolidone may increase the serotonergic activities of Esmirtazapine.Approved, Vet Approved
GabexateThe serum concentration of Esmirtazapine can be increased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Esmirtazapine can be increased when it is combined with Geldanamycin.Experimental
GM6001The serum concentration of Esmirtazapine can be increased when it is combined with GM6001.Experimental
GuanabenzEsmirtazapine may decrease the antihypertensive activities of Guanabenz.Approved
GuanfacineEsmirtazapine may decrease the antihypertensive activities of Guanfacine.Approved, Investigational
HaloperidolThe metabolism of Esmirtazapine can be decreased when combined with Haloperidol.Approved
HexobarbitalThe metabolism of Esmirtazapine can be increased when combined with Hexobarbital.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Esmirtazapine.Approved, Investigational
HydracarbazineHydracarbazine may increase the serotonergic activities of Esmirtazapine.Experimental
HydroxyamphetamineHydroxyamphetamine hydrobromide may decrease the sedative activities of Esmirtazapine.Approved
IdraparinuxThe serum concentration of Esmirtazapine can be increased when it is combined with idraparinux.Investigational
ImidaprilThe serum concentration of Esmirtazapine can be increased when it is combined with Imidapril.Investigational
ImipramineThe metabolism of Esmirtazapine can be decreased when combined with Imipramine.Approved
IndacaterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Indacaterol.Approved
IndinavirThe serum concentration of Esmirtazapine can be increased when it is combined with Indinavir.Approved
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Esmirtazapine.Approved
IproclozideIproclozide may increase the serotonergic activities of Esmirtazapine.Withdrawn
IproniazidIproniazid may increase the serotonergic activities of Esmirtazapine.Withdrawn
IsocarboxazidIsocarboxazid may increase the serotonergic activities of Esmirtazapine.Approved
IsoetarineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Isoetarine.Approved
IsoflurophateThe serum concentration of Esmirtazapine can be increased when it is combined with Isoflurophate.Approved, Withdrawn
IsoniazidThe metabolism of Esmirtazapine can be decreased when combined with Isoniazid.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Isoprenaline.Approved
IxazomibThe serum concentration of Esmirtazapine can be increased when it is combined with Ixazomib.Approved
KetoconazoleThe metabolism of Esmirtazapine can be decreased when combined with Ketoconazole.Approved, Investigational
LepirudinThe serum concentration of Esmirtazapine can be increased when it is combined with Lepirudin.Approved
LevothyroxineLevothyroxine may increase the arrhythmogenic activities of Esmirtazapine.Approved
LinagliptinThe serum concentration of Esmirtazapine can be increased when it is combined with Linagliptin.Approved
LinezolidLinezolid may increase the serotonergic activities of Esmirtazapine.Approved, Investigational
LiothyronineLiothyronine may increase the arrhythmogenic activities of Esmirtazapine.Approved, Vet Approved
LiotrixLiotrix may increase the arrhythmogenic activities of Esmirtazapine.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Esmirtazapine.Approved, Investigational
LisinoprilThe serum concentration of Esmirtazapine can be increased when it is combined with Lisinopril.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Esmirtazapine.Approved
LofexidineEsmirtazapine may decrease the antihypertensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Esmirtazapine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Esmirtazapine can be decreased when combined with Lorcaserin.Approved
LumefantrineThe metabolism of Esmirtazapine can be decreased when combined with Lumefantrine.Approved
MebanazineMebanazine may increase the serotonergic activities of Esmirtazapine.Withdrawn
MephedroneMephedrone may decrease the sedative activities of Esmirtazapine.Investigational
MephentermineEsmirtazapine may increase the vasopressor activities of Mephentermine.Approved
MetaraminolEsmirtazapine may increase the vasopressor activities of Metaraminol.Approved, Investigational
MethadoneThe metabolism of Esmirtazapine can be decreased when combined with Methadone.Approved
MethamphetamineEsmirtazapine may decrease the antihypertensive activities of Methamphetamine.Approved, Illicit
MethohexitalThe metabolism of Esmirtazapine can be increased when combined with Methohexital.Approved
MethotrimeprazineThe metabolism of Esmirtazapine can be decreased when combined with Methotrimeprazine.Approved
MethoxamineEsmirtazapine may increase the vasopressor activities of Methoxamine.Approved
Methylene blueEsmirtazapine may increase the serotonergic activities of Methylene blue.Investigational
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Esmirtazapine.Approved, Investigational
MethylphenobarbitalThe metabolism of Esmirtazapine can be increased when combined with Methylphenobarbital.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Esmirtazapine.Approved, Investigational
MetoprololThe metabolism of Esmirtazapine can be decreased when combined with Metoprolol.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Esmirtazapine.Approved
MidodrineEsmirtazapine may increase the vasopressor activities of Midodrine.Approved
MinaprineMinaprine may increase the serotonergic activities of Esmirtazapine.Approved
MirabegronThe metabolism of Esmirtazapine can be decreased when combined with Mirabegron.Approved
MMDAMMDA may decrease the sedative activities of Esmirtazapine.Experimental, Illicit
MoclobemideMoclobemide may increase the serotonergic activities of Esmirtazapine.Approved
MoexiprilThe serum concentration of Esmirtazapine can be increased when it is combined with Moexipril.Approved
MoxonidineThe therapeutic efficacy of Moxonidine can be decreased when used in combination with Esmirtazapine.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Esmirtazapine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Esmirtazapine can be increased when it is combined with Nafamostat.Approved, Investigational
NaphazolineEsmirtazapine may decrease the antihypertensive activities of Naphazoline.Approved
NelfinavirThe serum concentration of Esmirtazapine can be increased when it is combined with Nelfinavir.Approved
NevirapineThe metabolism of Esmirtazapine can be decreased when combined with Nevirapine.Approved
NialamideNialamide may increase the serotonergic activities of Esmirtazapine.Withdrawn
NicardipineThe metabolism of Esmirtazapine can be decreased when combined with Nicardipine.Approved
NicorandilEsmirtazapine may increase the hypotensive activities of Nicorandil.Approved
NilotinibThe metabolism of Esmirtazapine can be decreased when combined with Nilotinib.Approved, Investigational
NitroaspirinThe serum concentration of Esmirtazapine can be increased when it is combined with Nitroaspirin.Investigational
NorepinephrineEsmirtazapine may decrease the antihypertensive activities of Norepinephrine.Approved
OctamoxinOctamoxin may increase the serotonergic activities of Esmirtazapine.Withdrawn
OlodaterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Olodaterol.Approved
OmapatrilatThe serum concentration of Esmirtazapine can be increased when it is combined with Omapatrilat.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Orciprenaline.Approved
OtamixabanThe serum concentration of Esmirtazapine can be increased when it is combined with Otamixaban.Investigational
OxymetazolineEsmirtazapine may decrease the antihypertensive activities of Oxymetazoline.Approved
PaliperidoneEsmirtazapine may decrease the antihypertensive activities of Paliperidone.Approved
PanobinostatThe serum concentration of Esmirtazapine can be increased when it is combined with Panobinostat.Approved, Investigational
PargylinePargyline may increase the serotonergic activities of Esmirtazapine.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Esmirtazapine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Esmirtazapine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Esmirtazapine can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideEsmirtazapine may decrease the antihypertensive activities of Pergolide.Approved, Vet Approved, Withdrawn
PerindoprilThe serum concentration of Esmirtazapine can be increased when it is combined with Perindopril.Approved
PhenelzinePhenelzine may increase the serotonergic activities of Esmirtazapine.Approved
PhenindioneEsmirtazapine may increase the anticoagulant activities of Phenindione.Approved
PheniprazinePheniprazine may increase the serotonergic activities of Esmirtazapine.Withdrawn
PhenobarbitalThe metabolism of Esmirtazapine can be increased when combined with Phenobarbital.Approved
PhenoxypropazinePhenoxypropazine may increase the serotonergic activities of Esmirtazapine.Withdrawn
PhenprocoumonEsmirtazapine may increase the anticoagulant activities of Phenprocoumon.Approved
PhenterminePhentermine may decrease the sedative activities of Esmirtazapine.Approved, Illicit
PhenylephrineEsmirtazapine may increase the vasopressor activities of Phenylephrine.Approved
PhenylpropanolamineEsmirtazapine may decrease the antihypertensive activities of Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PhosphoramidonThe serum concentration of Esmirtazapine can be increased when it is combined with Phosphoramidon.Experimental
PirbuterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Pirbuterol.Approved
PirlindolePirlindole may increase the serotonergic activities of Esmirtazapine.Approved
PivhydrazinePivhydrazine may increase the serotonergic activities of Esmirtazapine.Withdrawn
PrimidoneThe metabolism of Esmirtazapine can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Esmirtazapine can be increased when it is combined with Prinomastat.Investigational
ProcaterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Procaterol.Approved
PromazineThe metabolism of Esmirtazapine can be decreased when combined with Promazine.Approved, Vet Approved
PseudoephedrineEsmirtazapine may decrease the antihypertensive activities of Pseudoephedrine.Approved
QuinaprilThe serum concentration of Esmirtazapine can be increased when it is combined with Quinapril.Approved, Investigational
QuinidineEsmirtazapine may increase the QTc-prolonging activities of Quinidine.Approved
QuinineThe metabolism of Esmirtazapine can be decreased when combined with Quinine.Approved
RacecadotrilThe serum concentration of Esmirtazapine can be increased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Esmirtazapine can be increased when it is combined with Ramipril.Approved
RanolazineThe metabolism of Esmirtazapine can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the serotonergic activities of Esmirtazapine.Approved
RemikirenThe serum concentration of Esmirtazapine can be increased when it is combined with Remikiren.Approved
RisperidoneEsmirtazapine may decrease the antihypertensive activities of Risperidone.Approved, Investigational
RitobegronRitobegron may decrease the sedative activities of Esmirtazapine.Investigational
RitodrineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Ritodrine.Approved
RitonavirThe metabolism of Esmirtazapine can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Esmirtazapine can be increased when it is combined with Rivaroxaban.Approved
RolapitantThe metabolism of Esmirtazapine can be decreased when combined with Rolapitant.Approved
RopiniroleEsmirtazapine may decrease the antihypertensive activities of Ropinirole.Approved, Investigational
SafrazineSafrazine may increase the serotonergic activities of Esmirtazapine.Withdrawn
SalbutamolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Salbutamol.Approved, Vet Approved
SalmeterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Salmeterol.Approved
SaquinavirThe serum concentration of Esmirtazapine can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Esmirtazapine can be increased when it is combined with Saxagliptin.Approved
SecobarbitalThe metabolism of Esmirtazapine can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineSelegiline may increase the serotonergic activities of Esmirtazapine.Approved, Investigational, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Esmirtazapine.Approved
SimeprevirThe serum concentration of Esmirtazapine can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Esmirtazapine can be increased when it is combined with Sitagliptin.Approved, Investigational
SpiraprilThe serum concentration of Esmirtazapine can be increased when it is combined with Spirapril.Approved
St. John's WortThe metabolism of Esmirtazapine can be increased when combined with St. John's Wort.Nutraceutical
StiripentolThe metabolism of Esmirtazapine can be decreased when combined with Stiripentol.Approved
TelaprevirThe serum concentration of Esmirtazapine can be increased when it is combined with Telaprevir.Withdrawn
TemocaprilThe serum concentration of Esmirtazapine can be increased when it is combined with Temocapril.Experimental, Investigational
TerbinafineThe metabolism of Esmirtazapine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerbutalineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Terbutaline.Approved
ThiamylalThe metabolism of Esmirtazapine can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Esmirtazapine can be increased when combined with Thiopental.Approved, Vet Approved
ThioridazineThe metabolism of Esmirtazapine can be decreased when combined with Thioridazine.Withdrawn
ThiorphanThe serum concentration of Esmirtazapine can be increased when it is combined with Thiorphan.Experimental
Thyroid, porcineThyroid, porcine may increase the arrhythmogenic activities of Esmirtazapine.Approved
TiclopidineThe metabolism of Esmirtazapine can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Esmirtazapine can be decreased when combined with Tipranavir.Approved, Investigational
TizanidineEsmirtazapine may decrease the antihypertensive activities of Tizanidine.Approved
ToloxatoneToloxatone may increase the serotonergic activities of Esmirtazapine.Approved
TramadolEsmirtazapine may increase the neuroexcitatory activities of Tramadol.Approved, Investigational
TrandolaprilThe serum concentration of Esmirtazapine can be increased when it is combined with Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the serotonergic activities of Esmirtazapine.Experimental
TranylcypromineTranylcypromine may increase the serotonergic activities of Esmirtazapine.Approved
UbenimexThe serum concentration of Esmirtazapine can be increased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Esmirtazapine can be increased when it is combined with Ulinastatin.Investigational
Valproic AcidThe serum concentration of Esmirtazapine can be increased when it is combined with Valproic Acid.Approved, Investigational
VenlafaxineThe metabolism of Esmirtazapine can be decreased when combined with Venlafaxine.Approved
VilanterolThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Vilanterol.Approved
VildagliptinThe serum concentration of Esmirtazapine can be increased when it is combined with Vildagliptin.Approved, Investigational
WarfarinEsmirtazapine may increase the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Esmirtazapine can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
XylometazolineEsmirtazapine may decrease the antihypertensive activities of Xylometazoline.Approved
YohimbineThe serum concentration of Yohimbine can be increased when it is combined with Esmirtazapine.Approved, Vet Approved
ZiprasidoneThe metabolism of Esmirtazapine can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. Teegarden BR, Al Shamma H, Xiong Y: 5-HT(2A) inverse-agonists for the treatment of insomnia. Curr Top Med Chem. 2008;8(11):969-76. [PubMed:18673166 ]
  2. Lewis V: Undertreatment of menopausal symptoms and novel options for comprehensive management. Curr Med Res Opin. 2009 Nov;25(11):2689-98. doi: 10.1185/03007990903240519. [PubMed:19775194 ]
External Links
PubChem Compound
3085218
PubChem Substance
310264876
ChemSpider
2342166
ChEMBL
CHEMBL1366933
Wikipedia
Esmirtazapine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Disorders, Intrinsic / Sleep Initiation and Maintenance Disorder; Elderly1
3CompletedTreatmentDyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Disorders, Intrinsic / Sleep Initiation and Maintenance Disorders1
3CompletedTreatmentDyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Initiation and Maintenance Disorders / Sleeplessness1
3CompletedTreatmentMenopause / Postmenopausal Syndrome / Vasomotor Symptoms1
3CompletedTreatmentMenopause / Vasomotor Symptoms1
3CompletedTreatmentSleeplessness3
3TerminatedTreatmentDyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Disorders, Intrinsic / Sleep Initiation and Maintenance Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)114 to 116Not Available
water solubilitySoluble in methanol and chloroform mg/mL (20 °C)Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.1 mg/mLALOGPS
logP2.9ALOGPS
logP3.21ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)6.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.66 m3·mol-1ChemAxon
Polarizability30.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as piperazinoazepines. These are compounds containing a piperazinoazepine skeleton, which consists of an azepine ring fused to a piperazine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperazinoazepines
Sub Class
Not Available
Direct Parent
Piperazinoazepines
Alternative Parents
Benzazepines / Dialkylarylamines / N-methylpiperazines / Azepines / Aralkylamines / Pyridines and derivatives / Imidolactams / Benzenoids / Heteroaromatic compounds / Trialkylamines
show 3 more
Substituents
Benzazepine / Piperazino-azepine / Dialkylarylamine / Azepine / N-methylpiperazine / N-alkylpiperazine / Aralkylamine / Imidolactam / Benzenoid / Pyridine
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Histamine receptor activity
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 catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Ivgy-May N, Ruwe F, Krystal A, Roth T: Esmirtazapine in non-elderly adult patients with primary insomnia: efficacy and safety from a randomized, 6-week sleep laboratory trial. Sleep Med. 2015 Jul;16(7):838-44. doi: 10.1016/j.sleep.2015.04.001. Epub 2015 Apr 16. [PubMed:26047892 ]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...

Components:
References
  1. Ivgy-May N, Ruwe F, Krystal A, Roth T: Esmirtazapine in non-elderly adult patients with primary insomnia: efficacy and safety from a randomized, 6-week sleep laboratory trial. Sleep Med. 2015 Jul;16(7):838-44. doi: 10.1016/j.sleep.2015.04.001. Epub 2015 Apr 16. [PubMed:26047892 ]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Thioesterase binding
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 oxymetazo...

Components:
References
  1. Ivgy-May N, Ruwe F, Krystal A, Roth T: Esmirtazapine in non-elderly adult patients with primary insomnia: efficacy and safety from a randomized, 6-week sleep laboratory trial. Sleep Med. 2015 Jul;16(7):838-44. doi: 10.1016/j.sleep.2015.04.001. Epub 2015 Apr 16. [PubMed:26047892 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase 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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Ramaekers JG, Conen S, de Kam PJ, Braat S, Peeters P, Theunissen EL, Ivgy-May N: Residual effects of esmirtazapine on actual driving performance: overall findings and an exploratory analysis into the role of CYP2D6 phenotype. Psychopharmacology (Berl). 2011 May;215(2):321-32. doi: 10.1007/s00213-010-2149-4. Epub 2011 Jan 19. [PubMed:21246188 ]
  2. Link [Link]
Drug created on March 19, 2008 10:48 / Updated on September 01, 2017 11:29