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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
Structure of MOLINDONE

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

HIDE SMILES / InChI

Molecular Formula C16H24N2O2
Molecular Weight 276.374
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Dystonic reaction during maintenance antipsychotic therapy.
1981 Jan
Drug interactions on spontaneous locomotor activity in rats. Neuroleptics and amphetamine-induced hyperactivity.
1984 Aug
Clinical experience with molindone hydrochloride in geriatric patients.
1985 Aug
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
Polydipsia and hyponatremia induced by multiple neuroleptics but not molindone.
1990 Apr
Neuroleptic-induced "painful legs and moving toes" syndrome: successful treatment with clonazepam and baclofen.
1990 Dec
Neuroleptic malignant syndrome possibly caused by molindone hydrochloride.
1991 Oct
Paroxetine-molindone interaction.
1995 Feb
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

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:04:38 GMT 2023
Edited
by admin
on Fri Dec 15 18:04:38 GMT 2023
Record UNII
RT3Y3QMF8N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOLINDONE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
MOLINDONE [HSDB]
Common Name English
MOLINDONE [MI]
Common Name English
molindone [INN]
Common Name English
3-ETHYL-6,7-DIHYDRO-2-METHYL-5-(MORPHOLINOMETHYL)INDOL-4(5H)-ONE
Systematic Name English
(±)-MOLINDONE
Common Name English
SPN-810
Common Name English
MOLINDONE [VANDF]
Common Name English
Molindone [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN05AE02
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
WHO-ATC N05AE02
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
NDF-RT N0000180182
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
LIVERTOX NBK548468
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL460
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
HSDB
3131
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
DRUG CENTRAL
1830
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PRIMARY
FDA UNII
RT3Y3QMF8N
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
WIKIPEDIA
MOLINDONE
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
EVMPD
SUB09042MIG
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PRIMARY
CAS
7416-34-4
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
MERCK INDEX
m7589
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY Merck Index
MESH
D008972
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PRIMARY
NCI_THESAURUS
C61850
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
RXCUI
7019
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY RxNorm
INN
2376
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
DAILYMED
RT3Y3QMF8N
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
SMS_ID
100000080357
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
IUPHAR
207
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023332
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
LACTMED
Molindone
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
DRUG BANK
DB01618
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
PUBCHEM
23897
Created by admin on Fri Dec 15 18:04:38 GMT 2023 , Edited by admin on Fri Dec 15 18:04:38 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC