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'''Esmirtazapine''' ('''ORG-50,081''') is a [[drug]] which was under development by [[Organon International|Organon]] for the treatment of [[insomnia]] and [[vasomotor]] [[symptom]]s (e.g., [[hot flash]]es) associated with [[menopause]].<ref name="urlFuture Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net">{{cite web | url = http://www.neurotransmitter.net/newdrugs.html | title = Future Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net | work = | accessdate = }}</ref><ref name="urlA Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov">{{cite web | url = http://clinicaltrials.gov/ct2/show/NCT00561574 | title = A Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov | format = | work = | accessdate = }}</ref><ref name="pmid18673166">{{cite journal | author = Teegarden BR, Al Shamma H, Xiong Y | title = 5-HT(2A) inverse-agonists for the treatment of insomnia | journal = Current Topics in Medicinal Chemistry | volume = 8 | issue = 11 | pages = 969–76 | year = 2008 | pmid = 18673166 | doi = 10.2174/156802608784936700| url = }}</ref><ref name="pmid19775194">{{cite journal | author = Lewis V | title = Undertreatment of menopausal symptoms and novel options for comprehensive management | journal = Current Medical Research and Opinion | volume = 25 | issue = 11 | pages = 2689–98 |date=November 2009 | pmid = 19775194 | doi = 10.1185/03007990903240519 | url = http://informahealthcare.com/doi/abs/10.1185/03007990903240519}}</ref> Esmirtazapine is the (''S'')-(+)-[[enantiomer]] of [[mirtazapine]] and possesses similar overall [[pharmacology]], including [[inverse agonist]] actions at [[H1 receptor|H<sub>1</sub>]] and [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s and [[receptor antagonist|antagonist]] actions at [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic receptor]]s.<ref name="urlFuture Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net"/><ref name="isbn0-521-88663-5">{{cite book | author = | title = Depression and bipolar disorder: Stahl's essential psychopharmacology | publisher = Cambridge University Press | location = Cambridge, UK | year = 2008 | pages = | isbn = 0-521-88663-5 | oclc = | doi = | url = http://books.google.com/?id=zqvVZOea2JAC&lpg=PA112&dq=esmirtazapine&pg=PA112#v=onepage&q=&f=false}}</ref> As of March 2010, Merck terminated internal clinical development program for esmirtazapine, for hot flashes and insomnia, for strategic reasons.<ref>http://www.merck.com/investors/financials/form-10-K-2009-final.pdf</ref>
'''Esmirtazapine''' ('''ORG-50,081''') is a [[drug]] which was under development by [[Organon International|Organon]] for the treatment of [[insomnia]] and [[vasomotor]] [[symptom]]s (e.g., [[hot flash]]es) associated with [[menopause]].<ref name="urlFuture Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net">{{cite web | url = http://www.neurotransmitter.net/newdrugs.html | title = Future Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net | work = | accessdate = }}</ref><ref name="urlA Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov">{{cite web | url = http://clinicaltrials.gov/ct2/show/NCT00561574 | title = A Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov | format = | work = | accessdate = }}</ref><ref name="pmid18673166">{{cite journal |vauthors=Teegarden BR, Al Shamma H, Xiong Y | title = 5-HT(2A) inverse-agonists for the treatment of insomnia | journal = Current Topics in Medicinal Chemistry | volume = 8 | issue = 11 | pages = 969–76 | year = 2008 | pmid = 18673166 | doi = 10.2174/156802608784936700| url = }}</ref><ref name="pmid19775194">{{cite journal | author = Lewis V | title = Undertreatment of menopausal symptoms and novel options for comprehensive management | journal = Current Medical Research and Opinion | volume = 25 | issue = 11 | pages = 2689–98 |date=November 2009 | pmid = 19775194 | doi = 10.1185/03007990903240519 | url = http://informahealthcare.com/doi/abs/10.1185/03007990903240519}}</ref> Esmirtazapine is the (''S'')-(+)-[[enantiomer]] of [[mirtazapine]] and possesses similar overall [[pharmacology]], including [[inverse agonist]] actions at [[H1 receptor|H<sub>1</sub>]] and [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s and [[receptor antagonist|antagonist]] actions at [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic receptor]]s.<ref name="urlFuture Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net"/><ref name="isbn0-521-88663-5">{{cite book | title = Depression and bipolar disorder: Stahl's essential psychopharmacology | publisher = Cambridge University Press | location = Cambridge, UK | year = 2008 | pages = | isbn = 0-521-88663-5 | oclc = | doi = | url = http://books.google.com/?id=zqvVZOea2JAC&lpg=PA112&dq=esmirtazapine&pg=PA112#v=onepage&q=&f=false}}</ref> As of March 2010, Merck terminated internal clinical development program for esmirtazapine, for hot flashes and insomnia, for strategic reasons.<ref>http://www.merck.com/investors/financials/form-10-K-2009-final.pdf</ref>


== See also ==
== See also ==
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[[Category:Serotonin antagonists]]
[[Category:Serotonin antagonists]]
[[Category:Tetracyclic antidepressants]]
[[Category:Tetracyclic antidepressants]]



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{{nervous-system-drug-stub}}

Revision as of 21:13, 26 May 2016

Esmirtazapine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
MetabolismLiver (CYP2D6)[1]
Identifiers
  • (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.056.994 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3
Molar mass265.35 g/mol g·mol−1
3D model (JSmol)
Melting point114 to 116 °C (237 to 241 °F)
Solubility in waterSoluble in methanol and chloroform mg/mL (20 °C)
  • CN1CCN2c3c(cccn3)Cc4ccccc4[C@H]2C1
  • 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 checkY
  • Key:RONZAEMNMFQXRA-MRXNPFEDSA-N checkY
  (verify)

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]

See also

References

  1. ^ "A population analysis on the effects of the CYP2D6 deficiency on pharmacokinetics and exposure of esmirtazapine in healthy volunteers" (PDF).
  2. ^ a b "Future Treatments for Depression, Anxiety, Sleep Disorders, Psychosis, and ADHD -- Neurotransmitter.net".
  3. ^ "A Long-Term Safety Study of Org 50081 in Elderly Outpatients With Chronic Primary Insomnia (176005)(P05697) - Full Text View - ClinicalTrials.gov".
  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.
  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.
  6. ^ Depression and bipolar disorder: Stahl's essential psychopharmacology. Cambridge, UK: Cambridge University Press. 2008. ISBN 0-521-88663-5.
  7. ^ http://www.merck.com/investors/financials/form-10-K-2009-final.pdf


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