Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H24N2O2 |
Molecular Weight | 276.374 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1=C(C)NC2=C1C(=O)C(CN3CCOCC3)CC2
InChI
InChIKey=KLPWJLBORRMFGK-UHFFFAOYSA-N
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01618 | http://reference.medscape.com/drug/moban-molindone-1000167 | https://www.drugs.com/cdi/molindone.html
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01618 | http://reference.medscape.com/drug/moban-molindone-1000167 | https://www.drugs.com/cdi/molindone.html
Molindone (Moban) is a therapeutic antipsychotic, used in the treatment of schizophrenia. The exact mechanism has not been established, however, based on electroencephalogram (EEG) studies, molindone is thought to act by occupying (antagonizing) dopamine (D2) receptor sites in the reticular limbic systems in the brain, thus decreasing dopamine activity. Decreased dopamine activity results in decreased physiological effects normally induced by excessive dopamine stimulation, such as those typically seen in manifestations of psychotic disorders. 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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12825922 |
265.0 nM [Ki] | ||
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28142338 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MOBAN Approved UseINDICATIONS AND USAGE. MOBAN is indicated for the management of schizophrenia. The efficacy of MOBAN in schizophrenia was established in clinical studies which enrolled newly hospitalized and chronically hospitalized, acutely ill, schizophrenic patients as subjects. Launch Date1974 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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482 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2861214/ |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MOLINDONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1897 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2861214/ |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MOLINDONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.76 μg × h/mL |
75 mg single, intramuscular dose: 75 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MOLINDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h |
75 mg single, intramuscular dose: 75 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MOLINDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
140 mg 1 times / day steady, oral Highest studied dose Dose: 140 mg, 1 times / day Route: oral Route: steady Dose: 140 mg, 1 times / day Sources: |
unhealthy, 8 -19 years Health Status: unhealthy Condition: Early-Onset Schizophrenia Age Group: 8 -19 years Sex: M+F Sources: |
|
76.5 mg 1 times / day steady, oral (mean) Dose: 76.5 mg, 1 times / day Route: oral Route: steady Dose: 76.5 mg, 1 times / day Sources: |
unhealthy, 8 -19 years n = 20 Health Status: unhealthy Condition: Early-Onset Schizophrenia Age Group: 8 -19 years Sex: M+F Population Size: 20 Sources: |
Disc. AE: Weight gain... AEs leading to discontinuation/dose reduction: Weight gain (4 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Weight gain | 4 patients Disc. AE |
76.5 mg 1 times / day steady, oral (mean) Dose: 76.5 mg, 1 times / day Route: oral Route: steady Dose: 76.5 mg, 1 times / day Sources: |
unhealthy, 8 -19 years n = 20 Health Status: unhealthy Condition: Early-Onset Schizophrenia Age Group: 8 -19 years Sex: M+F Population Size: 20 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Dystonic reaction during maintenance antipsychotic therapy. | 1981 Jan |
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Effect of alpha-methyl-p-tyrosine on neuroleptic-induced catalepsy in rat. | 1983 Jul-Sep |
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Drug interactions on spontaneous locomotor activity in rats. Neuroleptics and amphetamine-induced hyperactivity. | 1984 Aug |
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Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. | 1984 Sep |
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Clinical experience with molindone hydrochloride in geriatric patients. | 1985 Aug |
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Molindone hydrochloride treatment of hospitalized children with conduct disorder. | 1985 Aug |
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A case of massive rhabdomyolysis following molindone administration. | 1986 Dec |
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D-1 and D-2 receptor blockade have additive cataleptic effects in mice, but receptor effects may interact in opposite ways. | 1988 Feb |
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Relation of serum molindone levels to serum prolactin levels and antipsychotic response. | 1989 Oct |
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Polydipsia and hyponatremia induced by multiple neuroleptics but not molindone. | 1990 Apr |
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Neuroleptic-induced "painful legs and moving toes" syndrome: successful treatment with clonazepam and baclofen. | 1990 Dec |
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Neuroleptic malignant syndrome possibly caused by molindone hydrochloride. | 1991 Oct |
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Paroxetine-molindone interaction. | 1995 Feb |
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H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. | 2003 Mar |
|
Reversibility of dopamine receptor antagonist-induced hyperprolactinemia and associated histological changes in Tg RasH2 wild-type mice. | 2015 Dec |
Patents
Sample Use Guides
Initial Dosage Schedule The usual starting dosage is 50-75 mg/day. Increase to 100 mg/day in 3 or 4 days. Based on severity of symptomatology, dosage may be titrated up or down depending on individual patient response. An increase to 225 mg/day may be required in patients with severe symptomatology. Elderly and debilitated patients should be started on lower dosage.
Maintenance Dosage Schedule Mild-5 mg-15 mg three or four times a day. Moderate-10 mg-25 mg three or four times a day. Severe-225 mg/day may be required.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27040600
Salmonella typhimurium tester strains TA98, TA100, TA1535, TA1537 were used for Genotoxicity evaluation. S9 homogenates were added into a “mix” at a final concentration of 10% and the mix was supplemented with GSH (30 mM) and UDPGA (trisodium salt; 15 mM) as needed. The components of the S9 “mix” (per mL) included 0.7 mL water, 0.10 mL of 1M NaH2PO4/Na2HPO4 (pH 7.4), 0.02 mL of 0.25M glucose-6-phosphate, 0.04 mL of NADP, 0.04 mL of 0.825M KCl/0.2M MgCl2 and 0.1 mL of S9 homogenate. For the plate incorporation assay without S9, 100 mkL of tester strain and 50 mkL of vehicle control or test substance dilution were added to 2.5 mL of molten selective top agar (maintained at 45+/-2C). When S9 mix was required, 500 mkL of S9 mix, 100 mkL of tester strain and 50 mkL of vehicle control or Molindone dilution were added to 2.0 mL of molten selective agar. The top agar (100 mL) was supplemented with 0.5 mM histidine/biotin for the selection of histidine revertants (Salmonella tester strains) and 0.5 mM of tryptophan for the selection of tryptophan revertants (strain WP2uvrA). After the addition of the required components, the mixture was vortexed and overlaid (in 2.65 mL aliquots) onto the surface of 25 mL of minimal bottom agar contained in a 15 3 100 mm petri dish. Bacterial plates (triplicate plates/concentration/strain for each phase of the assay) were incubated for 5264 h at 378C before counting the revertants. The identification of a positive response was based on at least 2-fold (TA98, TA100, and WP2uvrA) or 3-fold (TA1535 and TA1537) increase in the mean revertants/plate accompanied by a dose-response to increasing concentrations of the Molindone.
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WHO-VATC |
QN05AE02
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WHO-ATC |
N05AE02
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NDF-RT |
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NBK548468
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NCI_THESAURUS |
C29710
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CHEMBL460
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RT3Y3QMF8N
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MOLINDONE
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SUB09042MIG
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m7589
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D008972
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C61850
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7019
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2376
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RT3Y3QMF8N
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Molindone
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DB01618
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23897
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)