Molindone

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Molindone
Clinical data
Pronunciation/moʊˈlɪndoʊn/ moh-LIN-dohn
Trade namesMoban
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682238
Pregnancy
category
  • C
Routes of
administration		By mouth (tablets)
Drug classTypical antipsychotic
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
JSmol)
  • O=C2c1c(c([nH]c1CCC2CN3CCOCC3)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, sold under the brand name Moban, is an antipsychotic which is used in the United States in the treatment of schizophrenia.[1][2] It works by blocking the effects of dopamine in the brain, leading to diminished symptoms of psychosis. It is rapidly absorbed when taken orally.

It is sometimes described as a typical antipsychotic,[3] and sometimes described as an atypical antipsychotic.[4]

Molindone was discontinued by its original supplier, Endo Pharmaceuticals, on January 13, 2010.[5]

Availability and marketing in the USA

After having been produced and subsequently discontinued by Core Pharma in 2015–2017, molindone is available again from Epic Pharma effective December, 2018.[6]

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.[4][7]

Chemistry

Synthesis

Patent:[8][9] Newer patent:[10]

Condensation of oximinoketone 2 (from

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. ^ "Molindone".
  3. PMID 19028375
    .
  4. ^
    PMID 17253473
    .
  5. ^ "Drugs to be Discontinued". www.fda.gov. Archived from the original on 2009-06-03.
  6. ^ "NEWS". www.epic-pharma.com. Retrieved 2018-12-12.
  7. S2CID 38635470
    .
  8. ^ SCHOEN KARL, J PACHTER IRWIN; BE 670798  (1965 to Endo Lab).
  9. ^ Irwin J Pachter, Karl Schoen, U.S. patent 3,491,093 (1970 to Endo Lab).
  10. ^ Martin Hanbauer, et al. WO2014042688 (Supernus Pharmaceuticals Inc).
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