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Identification
NameMolindone
Accession NumberDB01618
TypeSmall Molecule
GroupsApproved
Description

An indole derivative effective in schizophrenia and other psychoses and possibly useful in the treatment of the aggressive type of undersocialized conduct disorder. Molindone has much lower affinity for D2 receptors than most antipsychotic agents and has a relatively low affinity for D1 receptors. It has only low to moderate affinity for cholinergic and alpha-adrenergic receptors. Some electrophysiologic data from animals indicate that molindone has certain characteristics that resemble those of clozapine. (From AMA Drug Evaluations Annual, 1994, p283)

Structure
Thumb
Synonyms
(+-)-molindone
Moban
Molindona
Molindone
Molindonum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Molindone Hydrochloridetablet5 mg/1oralCore Pharma, Llc2015-09-15Not applicableUs
Molindone Hydrochloridetablet25 mg/1oralCore Pharma, Llc2015-09-15Not applicableUs
Molindone Hydrochloridetablet10 mg/1oralCore Pharma, Llc2015-09-15Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MobanNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Molindone hydrochloride
ThumbNot applicableDBSALT001243
Categories
UNIIRT3Y3QMF8N
CAS number7416-34-4
WeightAverage: 276.374
Monoisotopic: 276.183778022
Chemical FormulaC16H24N2O2
InChI KeyInChIKey=KLPWJLBORRMFGK-UHFFFAOYSA-N
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
IUPAC Name
3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one
SMILES
CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • Aryl alkyl ketone
  • Aryl ketone
  • Aralkylamine
  • Substituted pyrrole
  • Oxazinane
  • Morpholine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationMolindone is used for the management of the manifestations of psychotic disorders.
PharmacodynamicsMolindone is a dihydroindolone compound which is not structurally related to the phenothiazines, the butyrophenones, or the thioxanthenes. Molindone has a pharmacological profile in laboratory animals which predominantly resembles that of major tranquilizers causing reduction of spontaneous locomotion and aggressiveness, suppression of a conditioned response and antagonism of the bizarre stereotyped behavior and hyperactivity induced by amphetamines. In addition, molindone antagonizes the depression caused by the tranquilizing agent tetrabenazine.
Mechanism of actionThe 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.
Related Articles
AbsorptionRapidly absorbed from the gastrointestinal tract following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Most likely hepatic. 36 metabolites have been recognized, some of which may be active.

Route of eliminationHuman metabolic studies show molindone to be rapidly absorbed and metabolized when given orally. There are 36 recognized metabolites with less than 2-3% unmetabolized molindone being excreted in urine and feces.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9637
Caco-2 permeable+0.6401
P-glycoprotein substrateSubstrate0.7994
P-glycoprotein inhibitor IInhibitor0.828
P-glycoprotein inhibitor IIInhibitor0.6826
Renal organic cation transporterInhibitor0.5863
CYP450 2C9 substrateNon-substrate0.8202
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.637
CYP450 1A2 substrateNon-inhibitor0.6779
CYP450 2C9 inhibitorNon-inhibitor0.939
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.7549
CYP450 3A4 inhibitorInhibitor0.7739
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7134
Ames testNon AMES toxic0.6399
CarcinogenicityNon-carcinogens0.9336
BiodegradationNot ready biodegradable0.9909
Rat acute toxicity2.9352 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5259
hERG inhibition (predictor II)Inhibitor0.5804
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral10 mg/1
Tabletoral25 mg/1
Tabletoral5 mg/1
Prices
Unit descriptionCostUnit
Moban 50 mg tablet5.12USD tablet
Moban 25 mg tablet3.02USD tablet
Moban 10 mg tablet2.57USD tablet
Moban 5 mg tablet1.79USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point180.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.474 mg/mLALOGPS
logP2.09ALOGPS
logP2.04ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.34ChemAxon
pKa (Strongest Basic)6.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.06 m3·mol-1ChemAxon
Polarizability32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.41 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DrugSyn.org

US3491093
General ReferencesNot Available
External Links
ATC CodesN05AE02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Molindone.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Molindone.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Molindone.
AmphetamineMolindone may decrease the stimulatory activities of Amphetamine.
BenzphetamineMolindone may decrease the stimulatory activities of Benzphetamine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Molindone.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Molindone.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Molindone.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Molindone.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Molindone.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Molindone.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Molindone.
DextroamphetamineMolindone may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Molindone.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Molindone.
DonepezilDonepezil may increase the central neurotoxic activities of Molindone.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Molindone.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Molindone.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Molindone.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Molindone.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Molindone.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Molindone.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Molindone.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Molindone.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Molindone.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Molindone.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Molindone.
GalantamineGalantamine may increase the central neurotoxic activities of Molindone.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Molindone.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Molindone.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Molindone.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Molindone.
LisdexamfetamineMolindone may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Molindone.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Molindone.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Molindone.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Molindone.
MethamphetamineMolindone may decrease the stimulatory activities of Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Molindone is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Molindone.
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Molindone.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Molindone.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Molindone.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Molindone.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Molindone.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Molindone.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Molindone.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Molindone.
PhendimetrazineMolindone may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Molindone.
PhentermineMolindone may decrease the stimulatory activities of Phentermine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Molindone.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Molindone.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Molindone.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Molindone.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Molindone.
RivastigmineRivastigmine may increase the central neurotoxic activities of Molindone.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Molindone.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Molindone.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Molindone.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Molindone.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Molindone.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Molindone.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Molindone.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Molindone.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Molindone.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Molindone.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Molindone.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Molindone.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Molindone.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Molindone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Seeman P, Tallerico T: Antipsychotic drugs which elicit little or no parkinsonism bind more loosely than dopamine to brain D2 receptors, yet occupy high levels of these receptors. Mol Psychiatry. 1998 Mar;3(2):123-34. [PubMed:9577836 ]
  3. Lidow MS, Goldman-Rakic PS: Differential regulation of D2 and D4 dopamine receptor mRNAs in the primate cerebral cortex vs. neostriatum: effects of chronic treatment with typical and atypical antipsychotic drugs. J Pharmacol Exp Ther. 1997 Nov;283(2):939-46. [PubMed:9353417 ]
  4. Froimowitz M, Cody V: The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists. Drug Des Discov. 1997 Aug;15(2):63-81. [PubMed:9342550 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular Weight:
46106.335 Da
References
  1. Nguyen TV, Juorio AV: Down-regulation of tryptamine binding sites following chronic molindone administration. A comparison with responses of dopamine and 5-hydroxytryptamine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):366-71. [PubMed:2586632 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Nguyen TV, Juorio AV: Down-regulation of tryptamine binding sites following chronic molindone administration. A comparison with responses of dopamine and 5-hydroxytryptamine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):366-71. [PubMed:2586632 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Neeper R, Richelson E, Nelson A: Neuroleptic binding to muscarinic M2 receptors of normal human heart in vitro and comparison with binding to M1 and dopamine D2 receptors of brain. Neuropharmacology. 1991 May;30(5):527-9. [PubMed:1678146 ]
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Drug created on August 29, 2007 14:15 / Updated on August 17, 2016 12:23