Molindone

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.

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
IUPAC name
  • 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
Chemical and physical data
FormulaC16H24N2O2
Molar mass276.380 g·mol−1
3D model (JSmol)
SMILES
  • O=C2c1c(c([nH]c1CCC2CN3CCOCC3)C)CC
InChI
  • 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 Y
  • Key:KLPWJLBORRMFGK-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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
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. "Molindone".
  3. 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.
  4. Bagnall A, Fenton M, Kleijnen J, Lewis R (2007). Bagnall A (ed.). "Molindone for schizophrenia and severe mental illness". Cochrane Database Syst Rev (1): CD002083. doi:10.1002/14651858.CD002083.pub2. 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. Allison DB, Mentore JL, Heo M, et al. (1999). "Antipsychotic-induced weight gain: a comprehensive research synthesis". Am J Psychiatry. 156 (11): 1686–96. doi:10.1176/ajp.156.11.1686. PMID 10553730.
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