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| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 408764754
| verifiedrevid = 408764754
| IUPAC_name = 3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-<br>1,5,6,7-tetrahydro-4''H''-indol-4-one
| IUPAC_name = 3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-<br>1,5,6,7-tetrahydro-4''H''-indol-4-one
| image = Molindone.svg
| image = Molindone.svg
| width = 200

<!--Clinical data-->
<!--Clinical data-->
| pronounce = {{respell|moe|LIN|done}}
| tradename = Moban
| tradename = Moban
| Drugs.com = {{drugs.com|CDI|molindone}}
| Drugs.com = {{drugs.com|CDI|molindone}}
| MedlinePlus = a682238
| MedlinePlus = a682238
| pregnancy_category = C
| pregnancy_category = C
| legal_status = Rx-only
| legal_US = Rx-only
| routes_of_administration = Oral
| routes_of_administration = [[Oral administration|By mouth]] ([[Tablet (pharmacy)|tablets]])

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
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| elimination_half-life = 1.5 hours
| elimination_half-life = 1.5 hours
| excretion = Minor, [[kidney|renal]] and fecal
| excretion = Minor, [[kidney|renal]] and fecal

<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 460
| ChEMBL = 460

<!--Chemical data-->
<!--Chemical data-->
| C=16 | H=24 | N=2 | O=2
| C=16 | H=24 | N=2 | O=2
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It is sometimes described as a [[typical antipsychotic]],<ref name="pmid19028375">{{cite journal |vauthors=Aparasu RR, Jano E, Johnson ML, Chen H |title=Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients |journal=Am J Geriatr Pharmacother |volume=6 |issue=4 |pages=198–204 |date=October 2008 |pmid=19028375 |doi=10.1016/j.amjopharm.2008.10.003 |url=http://linkinghub.elsevier.com/retrieve/pii/S1543-5946(08)00055-X}}</ref> and sometimes described as an [[atypical antipsychotic]].<ref name="pmid17253473">{{cite journal |author=Bagnall A, Fenton M, Kleijnen J, Lewis R |title=Molindone for schizophrenia and severe mental illness |journal=Cochrane Database Syst Rev |volume= |issue=1 |pages=CD002083 |year=2007 |pmid=17253473 |doi=10.1002/14651858.CD002083.pub2 |editor1-last=Bagnall |editor1-first=Anne-Marie}}</ref>
It is sometimes described as a [[typical antipsychotic]],<ref name="pmid19028375">{{cite journal |vauthors=Aparasu RR, Jano E, Johnson ML, Chen H |title=Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients |journal=Am J Geriatr Pharmacother |volume=6 |issue=4 |pages=198–204 |date=October 2008 |pmid=19028375 |doi=10.1016/j.amjopharm.2008.10.003 |url=http://linkinghub.elsevier.com/retrieve/pii/S1543-5946(08)00055-X}}</ref> and sometimes described as an [[atypical antipsychotic]].<ref name="pmid17253473">{{cite journal |author=Bagnall A, Fenton M, Kleijnen J, Lewis R |title=Molindone for schizophrenia and severe mental illness |journal=Cochrane Database Syst Rev |volume= |issue=1 |pages=CD002083 |year=2007 |pmid=17253473 |doi=10.1002/14651858.CD002083.pub2 |editor1-last=Bagnall |editor1-first=Anne-Marie}}</ref>


Molindone was discontinued by its previous supplier, Endo Pharmaceuticals, on January 13, 2010.<ref name="FDA">http://www.fda.gov/Drugs/DrugSafety/DrugShortages/ucm050794.htm</ref>
Molindone was discontinued by its previous supplier, Endo Pharmaceuticals, on January 13, 2010.<ref name="FDA">http://www.fda.gov/Drugs/DrugSafety/DrugShortages/ucm050794.htm</ref> It is currently available in the U.S. from CorePharma under Abbreviated New Drug Application approved March 23, 2015.

It is currently available in the USA from COREPHARMA under ANDA approved March 23, 2015.


== Adverse effects ==
== Adverse effects ==

{{main|Typical antipsychotic}}
{{main|Typical antipsychotic}}

The side effect profile of molindone is similar to that of other typical antipsychotics. Unlike most antipsychotics, however, molindone use is associated with weight loss.<ref name="pmid17253473"/><ref>{{cite journal |author=Allison DB |title=Antipsychotic-induced weight gain: a comprehensive research synthesis |journal=[[American Journal of Psychiatry|Am J Psychiatry]] |volume=156 |issue=11 |pages=1686–96 |year=1999 |pmid=10553730 |doi= |name-list-format=vanc|author2=Mentore JL |author3=Heo M |display-authors=3 |last4=Chandler |first4=LP |last5=Cappelleri |first5=JC |last6=Infante |first6=MC |last7=Weiden |first7=PJ}} [http://ajp.psychiatryonline.org/doi/abs/10.1176/ajp.156.11.1686 Free full text]</ref>
The side effect profile of molindone is similar to that of other typical antipsychotics. Unlike most antipsychotics, however, molindone use is associated with weight loss.<ref name="pmid17253473"/><ref>{{cite journal |author=Allison DB |title=Antipsychotic-induced weight gain: a comprehensive research synthesis |journal=[[American Journal of Psychiatry|Am J Psychiatry]] |volume=156 |issue=11 |pages=1686–96 |year=1999 |pmid=10553730 |doi= |name-list-format=vanc|author2=Mentore JL |author3=Heo M |display-authors=3 |last4=Chandler |first4=LP |last5=Cappelleri |first5=JC |last6=Infante |first6=MC |last7=Weiden |first7=PJ}} [http://ajp.psychiatryonline.org/doi/abs/10.1176/ajp.156.11.1686 Free full text]</ref>


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== References ==
== References ==
{{Reflist}}
{{Reflist}}6. http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.DrugDetails<nowiki/>{{Antipsychotics}}

{{Antipsychotics}}
{{Dopaminergics}}
{{Dopaminergics}}


[[Category:Morpholines]]
[[Category:Indoles]]
[[Category:Indoles]]
[[Category:Ketones]]
[[Category:Ketones]]
[[Category:Atypical antipsychotics]]
[[Category:Morpholines]]
[[Category:Typical antipsychotics]]

Revision as of 15:39, 2 September 2016

Molindone
Clinical data
Pronunciationmoe-LIN-done
Trade namesMoban
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682238
Pregnancy
category
  • C
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
Elimination half-life1.5 hours
ExcretionMinor, renal and fecal
Identifiers
  • 3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-
    1,5,6,7-tetrahydro-4H-indol-4-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.254.109 Edit this at Wikidata
Chemical and physical data
FormulaC16H24N2O2
Molar mass276.374 g/mol g·mol−1
3D model (JSmol)
  • O=C2c1c(c(nc1CCC2CN3CCOCC3)C)CC
  • InChI=1S/C16H24N2O2/c1-3-13-11(2)17-14-5-4-12(16(19)15(13)14)10-18-6-8-20-9-7-18/h12,17H,3-10H2,1-2H3 checkY
  • Key:KLPWJLBORRMFGK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Molindone (Moban) is a therapeutic antipsychotic, used in the treatment of schizophrenia.[1] It works by blocking the effects of dopamine in the brain, leading to diminished psychoses. It is rapidly absorbed when taken orally.

It is sometimes described as a typical antipsychotic,[2] and sometimes described as an atypical antipsychotic.[3]

Molindone was discontinued by its previous supplier, Endo Pharmaceuticals, on January 13, 2010.[4] It is currently available in the U.S. from CorePharma under Abbreviated New Drug Application approved March 23, 2015.

Adverse effects

Main article: Typical antipsychotic

The side effect profile of molindone is similar to that of other typical antipsychotics. Unlike most antipsychotics, however, molindone use is associated with weight loss.[3][5]

Synthesis

Molindone synthesis: SCHOEN KARL, J PACHTER IRWIN; BE 670798  (1965 to Endo Lab).

Condensation of oximinoketone 2 (from nitrosation of 3-pentanone), with cyclohexane-1,3-dione (1) in the presence of zinc and acetic acid leads directly to the partly reduced indole derivative 6. The transformation may be rationalized by assuming as the first step, reduction of 2 to the corresponding α-aminoketone. Conjugate addition of the amine to 1 followed by elimination of hydroxide (as water) would give ene-aminoketone 3. This enamine may be assumed to be in tautomeric equilibrium with imine 4. Aldol condensation of the side chain carbonyl group with the doubly activated ring methylene group would then result in cyclization to pyrrole 5; simple tautomeric transformation would then give the observed product. Mannich reaction of 6 with formaldehyde and morpholine gives the tranquilizer molindone (7).

See also

References

  1. ^ "molindone". F.A. Davis Company.
  2. ^ Aparasu RR, Jano E, Johnson ML, Chen H (October 2008). "Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients". Am J Geriatr Pharmacother. 6 (4): 198–204. doi:10.1016/j.amjopharm.2008.10.003. PMID 19028375.
  3. ^ a b Bagnall A, Fenton M, Kleijnen J, Lewis R (2007). Bagnall, Anne-Marie (ed.). "Molindone for schizophrenia and severe mental illness". Cochrane Database Syst Rev (1): CD002083. doi:10.1002/14651858.CD002083.pub2. PMID 17253473.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ http://www.fda.gov/Drugs/DrugSafety/DrugShortages/ucm050794.htm
  5. ^ Allison DB; Mentore JL; Heo M; et al. (1999). "Antipsychotic-induced weight gain: a comprehensive research synthesis". Am J Psychiatry. 156 (11): 1686–96. PMID 10553730. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help) Free full text
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