Esmirtazapine

Esmirtazapine
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Pharmacokinetic data
Metabolism	Liver (CYP2D6)
Identifiers
	IUPAC name (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine;
CAS Number	61337-87-9 ;
PubChem CID	3085218; E. maleate: 6451144;
DrugBank	DB06678 ;
ChemSpider	2342166 ;
UNII	4685R51V7M;
KEGG	D04055 ;
ECHA InfoCard	100.056.994
Chemical and physical data
Formula	C17H19N3
Molar mass	265.360 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	114 to 116 °C (237 to 241 °F)
Solubility in water	Soluble in methanol and chloroform mg/mL (20 °C)
	SMILES CN1CCN2c3c(cccn3)Cc4ccccc4[C@H]2C1;
	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 ; Key:RONZAEMNMFQXRA-MRXNPFEDSA-N ;
	(what is this?)

Esmirtazapine (ORG-50,081) is a drug which was under development by Organon for the treatment of insomnia and vasomotor symptoms (e.g., hot flashes) associated with menopause.^[2]^[3]^[4]^[5] 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.^[2]^[6] As of March 2010, Merck terminated internal clinical development program for esmirtazapine, for hot flashes and insomnia, for strategic reasons.^[7]

References[]

^ "A population analysis on the effects of the CYP2D6 deficiency on pharmacokinetics and exposure of esmirtazapine in healthy volunteers" (PDF).
^ ^a ^b "Future Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net".
^ "A Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov". 7 January 2021. Cite journal requires |journal= (help)
^ Teegarden BR, Al Shamma H, Xiong Y (2008). "5-HT(2A) inverse-agonists for the treatment of insomnia". Current Topics in Medicinal Chemistry. 8 (11): 969–76. doi:10.2174/156802608784936700. PMID 18673166.
^ Lewis V (November 2009). "Undertreatment of menopausal symptoms and novel options for comprehensive management". Current Medical Research and Opinion. 25 (11): 2689–98. doi:10.1185/03007990903240519. PMID 19775194. S2CID 206964530.
^ Depression and bipolar disorder: Stahl's essential psychopharmacology. Cambridge, UK: Cambridge University Press. 2008. ISBN 978-0-521-88663-5.
^ http://www.merck.com/investors/financials/form-10-K-2009-final.pdf

External links[]

Media related to Esmirtazapine at Wikimedia Commons

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[urlwww.page-meeting.org-1] "A population analysis on the effects of the CYP2D6 deficiency on pharmacokinetics and exposure of esmirtazapine in healthy volunteers" (PDF).

[urlFuture_Treatments_for_Depression,_Anxiety,_Sleep_Disorders,_Psychosis,_and_ADHD_--_Neurotransmitter.net-2] "Future Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net".

[urlA_Long-Term_Safety_Study_of_Org_50081_in_Elderly_Outpatients_With_Chronic_Primary_Insomnia_(176005)(P05697)_-_Full_Text_View_-_ClinicalTrials.gov-3] "A Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov". 7 January 2021. Cite journal requires |journal= (help)

[pmid18673166-4] Teegarden BR, Al Shamma H, Xiong Y (2008). "5-HT(2A) inverse-agonists for the treatment of insomnia". Current Topics in Medicinal Chemistry. 8 (11): 969–76. doi:10.2174/156802608784936700. PMID 18673166.

[pmid19775194-5] Lewis V (November 2009). "Undertreatment of menopausal symptoms and novel options for comprehensive management". Current Medical Research and Opinion. 25 (11): 2689–98. doi:10.1185/03007990903240519. PMID 19775194. S2CID 206964530.

[isbn0-521-88663-5-6] Depression and bipolar disorder: Stahl's essential psychopharmacology. Cambridge, UK: Cambridge University Press. 2008. ISBN 978-0-521-88663-5.

[7] ttp://www.merck.com/investors/financials/form-10-K-2009-final.pdf

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v t Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (TCAs and TeCAs)	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Esmirtazapine Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Naranol Nitroxazepine Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline (teciptiline) Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Clocapramine Clorotepine Clotiapine Clozapine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Levomepromazine/Methotrimeprazine Loxapine Lurasidone Mesoridazine Metiapine Metitepine Mosapramine Naranol Olanzapine Oxyprothepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Trifluoperazine Triflupromazine Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Others	Adosopine Atiprosin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Methylene blue Monatepil Oxetorone Perlapine Pipazethate P7C3 Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Telenzepine Tropatepine

Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Pharmacokinetic data
Metabolism	Liver (CYP2D6)^[1]
Identifiers
IUPAC name (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
CAS Number	61337-87-9^Y
PubChem CID	3085218 E. maleate: 6451144
DrugBank	DB06678^N
ChemSpider	2342166^Y
UNII	4685R51V7M
KEGG	D04055^Y
ECHA InfoCard	100.056.994
Chemical and physical data
Formula	C₁₇H₁₉N₃
Molar mass	265.360 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	114 to 116 °C (237 to 241 °F)
Solubility in water	Soluble in methanol and chloroform mg/mL (20 °C)
SMILES CN1CCN2c3c(cccn3)Cc4ccccc4[C@H]2C1
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^Y Key:RONZAEMNMFQXRA-MRXNPFEDSA-N^Y
^NY (what is this?)

Esmirtazapine

See also[]

References[]

External links[]