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Identification
- Summary
Molindone is an antipsychotic used to treat schizophrenia.
- Generic Name
- Molindone
- DrugBank Accession Number
- DB01618
- Background
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)
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Molindone (DB01618)
- Weight
- Average: 276.374
Monoisotopic: 276.183778022 - Chemical Formula
- C16H24N2O2
- Synonyms
- (+/-)-molindone
- Molindona
- Molindone
- Molindonum
Pharmacology
- Indication
Molindone is used for the management of the manifestations of psychotic disorders.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Schizophrenia •••••••••••• - Contraindications & Blackbox Warnings
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Molindone 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 action
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.
Target Actions Organism AD(2) dopamine receptor antagonistHumans U5-hydroxytryptamine receptor 1A antagonistHumans U5-hydroxytryptamine receptor 2A antagonistHumans UMuscarinic acetylcholine receptor M1 other/unknownHumans - Absorption
Rapidly absorbed from the gastrointestinal tract following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Most likely hepatic. 36 metabolites have been recognized, some of which may be active.
- Route of elimination
Human 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-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Molindone is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Molindone is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Molindone. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Molindone. Agomelatine The risk or severity of CNS depression can be increased when Molindone is combined with Agomelatine. - Food Interactions
- Avoid alcohol. Severe CNS depression, which can be caused by alcohol, is a contraindication for molindone hydrochloride therapy.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Molindone hydrochloride 1DWS68PNE6 15622-65-8 GQWNECFJGBQMBO-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Moban Tablet 50 mg/1 Oral Endo Pharmaceuticals Inc. 1974-07-03 2009-11-23 US 
Moban Tablet 5 mg/1 Oral Endo Pharmaceuticals Inc. 1974-07-03 2010-05-25 US Moban Tablet 25 mg/1 Oral Endo Pharmaceuticals Inc. 1974-07-03 2009-08-24 US Moban Tablet 50 mg/1 Oral Physicians Total Care, Inc. 1974-07-03 2011-06-30 US Moban Tablet 100 mg/1 Oral Endo Pharmaceuticals Inc. 1974-07-03 2002-02-22 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Molindone Hydrochloride Tablet 10 mg/1 Oral Epic Pharma, LLC 2018-10-17 Not applicable US Molindone Hydrochloride Tablet 10 mg/1 Oral Core Pharma, Llc 2015-09-15 2018-02-28 US Molindone Hydrochloride Tablet 5 mg/1 Oral Epic Pharma, LLC 2018-10-17 Not applicable US Molindone Hydrochloride Tablet 5 mg/1 Oral Core Pharma, Llc 2015-09-15 2017-07-31 US Molindone Hydrochloride Tablet 25 mg/1 Oral Epic Pharma, LLC 2018-10-17 Not applicable US
Categories
- ATC Codes
- N05AE02 — Molindone
- Drug Categories
- Antidepressive Agents
- Antipsychotic Agents
- Antipsychotic Agents (First Generation [Typical])
- Central Nervous System Agents
- Central Nervous System Depressants
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Heterocyclic Compounds, Fused-Ring
- Indole Derivatives
- Indoles
- Nervous System
- Neurotoxic agents
- Psycholeptics
- Psychotropic Drugs
- Serotonin 5-HT1 Receptor Antagonists
- Serotonin 5-HT1A Receptor Antagonists
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Not Available
- Direct Parent
- Indoles and derivatives
- Alternative Parents
- Aryl alkyl ketones / Aralkylamines / Substituted pyrroles / Morpholines / Vinylogous amides / Heteroaromatic compounds / Trialkylamines / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds show 3 more
- Substituents
- Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- indoles (CHEBI:6965)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- RT3Y3QMF8N
- CAS number
- 7416-34-4
- InChI Key
- 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-yl)methyl]-4,5,6,7-tetrahydro-1H-indol-4-one
- SMILES
- CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2
References
- Synthesis Reference
- US3491093
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015555
- KEGG Drug
- D08226
- KEGG Compound
- C07230
- PubChem Compound
- 23897
- PubChem Substance
- 46504744
- ChemSpider
- 22342
- BindingDB
- 50130290
- 7019
- ChEBI
- 6965
- ChEMBL
- CHEMBL460
- Therapeutic Targets Database
- DAP000979
- PharmGKB
- PA164746756
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Molindone
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bristol-Myers Squibb Co.
- Endo Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Tablet Oral 100 mg/1 Tablet Oral 50 mg/1 Tablet Oral 10 mg/1 Tablet Oral 25 mg/1 Tablet Oral 5 mg/1 - Prices
Unit description Cost Unit Moban 50 mg tablet 5.12USD tablet Moban 25 mg tablet 3.02USD tablet Moban 10 mg tablet 2.57USD tablet Moban 5 mg tablet 1.79USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 180.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.474 mg/mL ALOGPS logP 2.09 ALOGPS logP 2.04 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 15.43 Chemaxon pKa (Strongest Basic) 6.65 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 45.33 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 81.06 m3·mol-1 Chemaxon Polarizability 32 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9637 Caco-2 permeable + 0.6401 P-glycoprotein substrate Substrate 0.7994 P-glycoprotein inhibitor I Inhibitor 0.828 P-glycoprotein inhibitor II Inhibitor 0.6826 Renal organic cation transporter Inhibitor 0.5863 CYP450 2C9 substrate Non-substrate 0.8202 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.637 CYP450 1A2 substrate Non-inhibitor 0.6779 CYP450 2C9 inhibitor Non-inhibitor 0.939 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.7549 CYP450 3A4 inhibitor Inhibitor 0.7739 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7134 Ames test Non AMES toxic 0.6399 Carcinogenicity Non-carcinogens 0.9336 Biodegradation Not ready biodegradable 0.9909 Rat acute toxicity 2.9352 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5259 hERG inhibition (predictor II) Inhibitor 0.5804
Spectra
- Mass Spec (NIST)
- Download (9.41 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001j-7690000000-39a1949956d6f8459274 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0290000000-1decadf2de366c0109dc Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-f19a97ca8dca33e6c7b4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0iml-1940000000-deb07ed174bd49a1b3e0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-d2df5eb506b0a1500479 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03fs-1940000000-929c36a09b928f098cb9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05fu-1920000000-cf324ae57df84d9a85a6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 179.8822057 predictedDarkChem Lite v0.1.0 [M-H]- 164.50879 predictedDeepCCS 1.0 (2019) [M+H]+ 179.3408057 predictedDarkChem Lite v0.1.0 [M+H]+ 166.86678 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.9884057 predictedDarkChem Lite v0.1.0 [M+Na]+ 172.95995 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- Dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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 proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895). 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) (PubMed:28129538). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors (PubMed:28129538). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538). Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores (PubMed:18703043, PubMed:28129538). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other/unknown
- General 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
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- 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. [Article]
Drug created at August 29, 2007 20:15 / Updated at June 02, 2024 21:54