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SPN 810, SPN 801M, AFX 2201
cas 15622-65-8 hcl
Molindone is used for the management of the manifestations of psychotic disorders.
Supernus Pharmaceuticals , under license from Afecta Pharmaceuticals , is developing molindone hydrochloride (SPN-810; SPN-801M; AFX-2201; presumed to be Zalvari), as a capsule formulation, for the potential oral treatment of conduct disorder in patients with attention deficit hyperactivity disorder. In 3Q15, the company initiated two phase III trials (CHIME 1 and CHIME 2) for compulsive aggression in ADHD. In November 2019, the trial was expected to complete in June 2020.
Molindone, sold under the brand name Moban, is an antipsychotic which is used in the United States in the treatment of schizophrenia. 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 was discontinued by its original supplier, Endo Pharmaceuticals, on January 13, 2010.
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.
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).
Process for preparing molindone and its intermediates useful for treating schizophrenia..
Molindone is chemically known as 4H-Indol-4-one, 3-ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl) and represented by formula I. Molindone is indicated for management of schizophrenia and is under clinical trial for alternate therapies.
Example 1: Preparation of methyl 2-chloro-2-ethyl-3-oxobutanoate
Example 2: Preparation of 3-chloropentan-2-one
Example 3: Preparation of 3-chloropentan-2-one
Example 4: Preparation of 2-(2-oxopentan-3-yl)cyclohexane-1,3-dione (4)
Example 5: Preparation of 2-methyl-3-ethyl-4-oxo-4,5,6,7-tetrahydroindole (5)
Example 6: Preparation of 2-methyl-3-ethyl-4-oxo-4,5,6,7-tetrahydroindole (5)
Example 7: Preparation of Molindone Hydrochloride
- “molindone”. F.A. Davis Company.
- 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.
- 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.
- “NEWS”. http://www.epic-pharma.com. Retrieved 2018-12-12.
- 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 (inactive 2020-01-22). PMID 10553730. Free full text
|AHFS/Drugs.com||Consumer Drug Information|
|By mouth (tablets)|
|Elimination half-life||1.5 hours|
|Excretion||Minor, renal and fecal|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||276.380 g·mol−1|
|3D model (JSmol)|
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