3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one

• ChemBase ID: 1394
• Molecular Formular: C16H24N2O2
• Molecular Mass: 276.37396
• Monoisotopic Mass: 276.18377802
• SMILES: O1CCN(CC2CCc3[nH]c(c(c3C2=O)CC)C)CC1
• Canonical SMILES: CCc1c(C)[nH]c2c1C(=O)C(CC2)CN1CCOCC1
• 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
• InChIKey: KLPWJLBORRMFGK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one
• IUPAC Traditional name: molindone
• Brand Name: Moban
• Synonyms: 3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one; (+-)-molindone; Molindona [inn-spanish]; Molindonum [inn-latin]; Molindone

Database IDs

• CAS Number: 7416-34-4
• MDL Number: MFCD00866709
• PubChem SID: 160964854; 46504744
• PubChem CID: 23897
• ATC CODE: N05AE02
• CHEMBL: 460
• Chemspider ID: 22342
• DrugBank ID: DB01618
• IUPHAR ligand ID: 207
• KEGG ID: D08226
• Unique Ingredient Identifier: RT3Y3QMF8N
• Wikipedia Title: Molindone
• Medline Plus: a682238

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.337675
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.8571428
• LogD (pH = 7.4): 1.9640257
• Log P: 2.035115
• Molar Refractivity: 81.0594 cm^3
• Polarizability: 30.793152 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -2.77
• Solubility (Water): 4.74e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 179 - 181°C
• Hydrophobicity(logP): 2.572

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Minor, renal and fecal
• Half Life: 1.5 hours
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: C

Product Information

• Purity: 95%

DETAILS

DrugBank - DB01618

• Drug Groups: approved
• 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)
• Indication: Molindone is used for the management of the manifestations of psychotic disorders.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Most likely hepatic. 36 metabolites have been recognized, some of which may be active.
• Absorption: Rapidly absorbed from the gastrointestinal tract following oral administration.
• 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.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com