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<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_category =
| pregnancy_category =
| legal_status = Uncontrolled
| legal_status = Uncontrolled
| routes_of_administration = [[Mouth|Oral]]
| routes_of_administration = [[Mouth|Oral]]


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| metabolism = Liver ([[CYP2D6]])<ref name="urlwww.page-meeting.org">{{cite web | url = http://www.page-meeting.org/pdf_assets/2259-posterPAGE2008_SP.pdf | title = A population analysis on the effects of the CYP2D6 deficiency on pharmacokinetics and exposure of esmirtazapine in healthy volunteers}}</ref>
| metabolism = Liver ([[CYP2D6]])<ref name="urlwww.page-meeting.org">{{cite web | url = http://www.page-meeting.org/pdf_assets/2259-posterPAGE2008_SP.pdf | title = A population analysis on the effects of the CYP2D6 deficiency on pharmacokinetics and exposure of esmirtazapine in healthy volunteers}}</ref>
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
Line 21: Line 21:
| CAS_number = 61337-87-9
| CAS_number = 61337-87-9
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| PubChem = 6451144
| PubChem2 = 6451144
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2342166
| ChemSpiderID = 2342166
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
Line 29: Line 29:
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04055
| KEGG = D04055
| PubChem = 3085218


<!--Chemical data-->
<!--Chemical data-->
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| molecular_weight = 381.43 g/mol
| molecular_weight = 381.43 g/mol
| smiles = CN1CCN2C(C1)C3=CC=CC=C3CC4=C2N=CC=C4
| smiles = CN1CCN2C(C1)C3=CC=CC=C3CC4=C2N=CC=C4
| PubChem = 3085218
| PubChem = 3085218
| InChI = 1/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
| InChI = 1/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
| InChIKey = RONZAEMNMFQXRA-MRXNPFEDBJ
| InChIKey = RONZAEMNMFQXRA-MRXNPFEDBJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RONZAEMNMFQXRA-MRXNPFEDSA-N
| StdInChIKey = RONZAEMNMFQXRA-MRXNPFEDSA-N
| melting_point = 114
| melting_point = 114

Revision as of 01:19, 27 November 2014

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
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.056.994 Edit this at Wikidata
Chemical and physical data
FormulaC21H23N3O4
Molar mass381.43 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)
  • CN1CCN2C(C1)C3=CC=CC=C3CC4=C2N=CC=C4
  • 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] As of 2009 it is in phase III clinical trials.[2] 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 c "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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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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