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Details

Stereochemistry RACEMIC
Molecular Formula C16H24N2O2.ClH
Molecular Weight 312.835
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOLINDONE HYDROCHLORIDE

SMILES

Cl.CCC1=C(C)NC2=C1C(=O)C(CN3CCOCC3)CC2

InChI

InChIKey=GQWNECFJGBQMBO-UHFFFAOYSA-N
InChI=1S/C16H24N2O2.ClH/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;1H

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
265.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MOBAN

Approved Use

INDICATIONS 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 Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
482 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1897 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
PubMed

PubMed

TitleDatePubMed
A case of massive rhabdomyolysis following molindone administration.
1986 Dec
D-1 and D-2 receptor blockade have additive cataleptic effects in mice, but receptor effects may interact in opposite ways.
1988 Feb
Relation of serum molindone levels to serum prolactin levels and antipsychotic response.
1989 Oct
Neuroleptic malignant syndrome possibly caused by molindone hydrochloride.
1991 Oct
Paroxetine-molindone interaction.
1995 Feb
Patents

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
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.
Name Type Language
MOLINDONE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
3-Ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)indol-4(5H)-one monohydrochloride
Systematic Name English
MOLINDONE HYDROCHLORIDE [USAN]
Common Name English
4H-INDOL-4-ONE, 3-ETHYL-1,5,6,7-TETRAHYDRO-2-METHYL-5-(4-MORPHOLINYLMETHYL)-, MONOHYDROCHLORIDE
Common Name English
MOLINDONE HYDROCHLORIDE [USP-RS]
Common Name English
MOLINDONE HCL
Common Name English
MOLINDONE HYDROCHLORIDE [VANDF]
Common Name English
MOLINDONE HYDROCHLORIDE [MART.]
Common Name English
Molindone hydrochloride [WHO-DD]
Common Name English
EN-1733A
Code English
MOBAN
Brand Name English
MOLINDONE HYDROCHLORIDE [USP IMPURITY]
Common Name English
MOLINDONE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
MOLINDONE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
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Code System Code Type Description
EVMPD
SUB14587MIG
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PRIMARY
EPA CompTox
DTXSID5045417
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PRIMARY
PUBCHEM
27421
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PRIMARY
DRUG BANK
DBSALT001243
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PRIMARY
RXCUI
82051
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PRIMARY RxNorm
FDA UNII
1DWS68PNE6
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PRIMARY
MERCK INDEX
m7589
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PRIMARY Merck Index
SMS_ID
100000076232
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PRIMARY
DAILYMED
1DWS68PNE6
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PRIMARY
RS_ITEM_NUM
1445459
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PRIMARY
NCI_THESAURUS
C47624
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PRIMARY
ChEMBL
CHEMBL460
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PRIMARY
CAS
15622-65-8
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PRIMARY