- 同
- molindone hydrochloride
WordNet
- a disorderly crowd of people (同)rabble, rout
PrepTutorEJDIC
- 〈C〉(無秩序な)『群衆』,暴徒,やじ馬 / 〈C〉(一般に,人・動物・物の)群れ,集まり《+『of』+『名』》 / 《the ~》大衆,民衆(the masses) / 《話》(盗賊・ギャングなどの)一団,一味 / …‘の'回りに熱狂して集まる;…‘に'大勢で押し寄せる
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/03/15 05:54:55」(JST)
[Wiki en表示]
Molindone
|
Systematic (IUPAC) name |
3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-
1,5,6,7-tetrahydro-4H-indol-4-one
|
Clinical data |
Trade names |
Moban |
AHFS/Drugs.com |
Consumer Drug Information |
MedlinePlus |
a682238 |
Pregnancy
category |
|
Routes of
administration |
Oral |
Legal status |
|
Pharmacokinetic data |
Metabolism |
Hepatic |
Biological half-life |
1.5 hours |
Excretion |
Minor, renal and fecal |
Identifiers |
CAS Number |
7416-34-4 Y |
ATC code |
N05AE02 (WHO) |
PubChem |
CID 23897 |
IUPHAR/BPS |
207 |
DrugBank |
DB01618 N |
ChemSpider |
22342 Y |
UNII |
RT3Y3QMF8N Y |
KEGG |
D08226 Y |
ChEMBL |
CHEMBL460 Y |
Chemical data |
Formula |
C16H24N2O2 |
Molar mass |
276.374 g/mol |
SMILES
-
O=C2c1c(c(nc1CCC2CN3CCOCC3)C)CC
|
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 Y
-
Key:KLPWJLBORRMFGK-UHFFFAOYSA-N Y
|
NY (what is this?) (verify) |
Molindone (Moban) is a therapeutic antipsychotic, used in the treatment of schizophrenia.[1] It works by blocking the effects of dopamine in the brain, leading to diminished psychoses. It is rapidly absorbed when taken orally.
It is sometimes described as a typical antipsychotic,[2] and sometimes described as an atypical antipsychotic.[3]
Molindone was discontinued by its sole supplier, Endo Pharmaceuticals, on January 13, 2010. [4]
Contents
- 1 Adverse effects
- 2 Synthesis
- 3 See also
- 4 References
Adverse effects
Main article: Typical antipsychotic
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.[3][5]
Synthesis
Molindone synthesis: SCHOEN KARL, J PACHTER IRWIN;
BE 670798 (1965 to Endo Lab).
Condensation of oximinoketone 2 (from nitrosation of 3-pentanone), with 1,3-cyclohexanedione (1) in the presence of zinc and acetic acid leads directly to the partly reduced indole derivative 6. The transformation may be rationalized by assuming as the first step, reduction of 2 to the corresponding α-aminoketone. Conjugate addition of the amine to 1 followed by elimination of hydroxide (as water) would give ene-aminoketone 3. This enamine may be assumed to be in tautomeric equilibrium with imine 4. Aldol condensation of the side chain carbonyl group with the doubly activated ring methylene[disambiguation needed] would then result in cyclization to pyrrole 5; simple tautomeric transformation would then give the observed product. Mannich reaction of 6 with formaldehyde and morpholine gives the tranquilizer molindone (7).
See also
References
- ^ "molindone". F.A. Davis Company.
- ^ Aparasu RR, Jano E, Johnson ML, Chen H (October 2008). "Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients". Am J Geriatr Pharmacother 6 (4): 198–204. doi:10.1016/j.amjopharm.2008.10.003. PMID 19028375.
- ^ a b Bagnall A, Fenton M, Kleijnen J, Lewis R (2007). Bagnall, Anne-Marie, ed. "Molindone for schizophrenia and severe mental illness". Cochrane Database Syst Rev (1): CD002083. doi:10.1002/14651858.CD002083.pub2. PMID 17253473.
- ^ http://www.fda.gov/Drugs/DrugSafety/DrugShortages/ucm050794.htm
- ^ Allison DB, Mentore JL, Heo M, et al. (1999). "Antipsychotic-induced weight gain: a comprehensive research synthesis". Am J Psychiatry 156 (11): 1686–96. PMID 10553730. Free full text
Antipsychotics (neuroleptics) (N05A)
|
|
Typical |
- Benzamides
- Levosulpiride
- Sulpiride
- Veralipride‡
- Butyrophenones
- Aceperone
- Azaperone
- Benperidol
- Bromperidol
- Droperidol
- Fluanisone
- Haloperidol#
- Lenperone
- Moperone
- Pipamperone
- Spiperone
- Timiperone
- Trifluperidol
- Diphenylbutylpiperidines
- Clopimozide
- Fluspirilene
- Penfluridol
- Pimozide
- Phenothiazines
- Acepromazine
- Acetophenazine
- Butaperazine
- Carphenazine
- Chloracizine
- Chlorproethazine
- Chlorpromazine
- Cyamemazine
- Dixyrazine
- Fluacizine
- Fluphenazine
- Levomepromazine/Methotrimeprazine
- Mesoridazine
- Perazine
- Periciazine
- Perphenazine
- Perphenazine 4-aminobutyrate
- Piperacetazine
- Pipotiazine
- Prochlorperazine
- Promazine
- Promethazine
- Propiomazine
- Sulforidazine
- Thiethylperazine
- Thiopropazate
- Thioproperazine
- Thioridazine
- Trifluoperazine
- Triflupromazine
- Thioxanthenes
- Chlorprothixene
- Clopenthixol
- Clothixamide
- Flupentixol
- Fluprothixene
- Piflutixol
- Teflutixol
- Thiothixene
- Zuclopenthixol
- Tricyclics
- Fluotracen
- Loxapine
- Trimipramine
- Others
- Butaclamol
- Prothipendyl
|
|
Atypical |
- Benzamides
- Amisulpride
- Nemonapride
- Remoxipride‡
- Sultopride
- Tiapride
- Butyrophenones
- Cinuperone
- Melperone
- Setoperone
- Benzo(iso)oxazolepiperidines
- Iloperidone
- Ocaperidone§
- Paliperidone
- Risperidone#
- Benzo(iso)thiazolepiperazines
- Lurasidone
- Perospirone
- Revospirone§
- Tiospirone§
- Ziprasidone
- Diphenylbutylpiperazines
- Amperozide
- Phenylpiperazines
- Aripiprazole
- Aripiprazole lauroxil
- Bifeprunox§
- Brexpiprazole
- Cariprazine
- Tricyclics
- Amoxapine
- Asenapine
- Carpipramine
- Clocapramine
- Clorotepine
- Clotiapine
- Clozapine#
- Fluperlapine
- Gevotroline
- Metitepine
- Mosapramine
- Olanzapine
- Quetiapine
- Tenilapine
- Zotepine
- Others
- Blonanserin
- ITI-007†
- Molindone
- Pimavanserin
- RP5063†
- Sertindole
- Zicronapine§
|
|
Others |
- Azacyclonol
- Cannabidiol
- Oxypertine
- Reserpine
- Tetrabenazine
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
Dopaminergics
|
|
Receptor ligands
|
|
DR |
Agonists |
- Adamantanes
- Amantadine
- Memantine
- Rimantadine
|
|
- Aminotetralins
- 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232
|
|
- Benzazepines
- 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959
|
|
- Ergolines
- Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Lisuride
- LSD
- Pergolide
|
|
- Dihydrexidine derivatives
- 2-OH-NPA
- A-86929
- Adrogolide (ABT-431, DAS-431)
- Ciladopa
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine
|
|
- Others
- A-68930
- A-77636
- A-412,997
- ABT-670
- ABT-724
- Aplindore
- Apomorphine
- Aripiprazole
- Arketamine
- Bifeprunox
- BP-897
- Captodiame
- CY-208,243
- Dizocilpine
- Esketamine
- Etilevodopa
- Flibanserin
- Ketamine
- Melevodopa
- Modafinil
- Pardoprunox
- Phencyclidine
- PD-128,907
- PD-168,077
- PF-219,061
- Piribedil
- Pramipexole
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Rotigotine
- Roxindole
- Salvinorin A
- SKF-89,145
- Sumanirole
- Terguride
- Umespirone
- WAY-100,635
|
|
|
Antagonists |
- Typical antipsychotics
- Acepromazine
- Azaperone
- Benperidol
- Bromperidol
- Clopenthixol
- Chlorpromazine
- Chlorprothixene
- Droperidol
- Flupentixol
- Fluphenazine
- Fluspirilene
- Haloperidol
- Levomepromazine
- Levosulpiride
- Loxapine
- Mesoridazine
- Nemonapride
- Penfluridol
- Perazine
- Periciazine
- Perphenazine
- Pimozide
- Prochlorperazine
- Promazine
- Sulforidazine
- Sulpiride
- Sultopride
- Thioridazine
- Thiothixene
- Trifluoperazine
- Triflupromazine
- Trifluperidol
- Zuclopenthixol
|
|
- Atypical antipsychotics
- Amisulpride
- Asenapine
- Blonanserin
- Cariprazine
- Carpipramine
- Clocapramine
- Clorotepine
- Clozapine
- Gevotroline
- Iloperidone
- Lurasidone
- Melperone
- Molindone
- Mosapramine
- Olanzapine
- Paliperidone
- Perospirone
- Piquindone
- Quetiapine
- Remoxipride
- Risperidone
- Sertindole
- Tiospirone
- Zicronapine
- Ziprasidone
- Zotepine
|
|
- Antiemetics
- AS-8112
- Alizapride
- Bromopride
- Clebopride
- Domperidone
- Metoclopramide
- Thiethylperazine
|
|
- Others
- Amoxapine
- Buspirone
- Butaclamol
- Ecopipam
- EEDQ
- Eticlopride
- Fananserin
- Hydroxyzine
- L-745,870
- Nafadotride
- Nuciferine
- PNU-99,194
- Raclopride
- Sarizotan
- SB-277,011-A
- SCH 23390
- SKF-83,959
- Sonepiprazole
- Spiperone
- Spiroxatrine
- Stepholidine
- Tetrahydropalmatine
- Tiapride
- UH-232
- Yohimbine
|
|
|
|
|
|
Reuptake modulators
|
|
DAT |
Inhibitors |
- Piperazines
- DBL-583
- GBR-12783
- GBR-12935
- GBR-13069
- GBR-13098
- Nefazodone
- Vanoxerine
|
|
- Piperidines
- 4-Fluoropethidine
- Benocyclidine (BTCP)
- Desoxypipradrol
- Dexmethylphenidate
- Difemetorex
- Ethylphenidate
- HDMP-28
- Methylphenidate
- Pethidine (meperidine)
- Phencyclidine
- Pipradrol
|
|
- Pyrrolidines
- Diphenylprolinol
- MDPV
- Naphyrone
- Prolintane
- Pyrovalerone
|
|
- Tropanes
- Altropane
- Benzatropine (benztropine)
- Brasofensine
- CFT
- Cocaine
- Dichloropane
- Difluoropine
- Etybenzatropine (ethybenztropine)
- FE-β-CPPIT
- FP-β-CPPIT
- Ioflupane (123I)
- RTI-55
- RTI-112
- RTI-113
- RTI-121
- RTI-126
- RTI-150
- RTI-177
- RTI-229
- RTI-336
- Tenocyclidine
- Tesofensine
- Troparil
- Tropoxane
- WF-11
- WF-23
- WF-31
- WF-33
|
|
- Others
- Adrafinil
- Amifitadine
- Armodafinil
- Amfonelic acid
- Amineptine
- Ansofaxine
- BTQ
- BTS 74,398
- Bupropion
- Chaenomeles speciosa
- Ciclazindol
- Dasotraline
- Desmethylsertraline
- Diclofensine
- Dimethocaine
- Diphenylpyraline
- Dizocilpine (MK-801)
- DOV-102,677
- DOV-216,303
- Efavirenz
- Esketamine
- EXP-561
- Fencamfamine
- Fezolamine
- Fluorenol
- GYKI-52895
- Indatraline
- Ketamine
- Lefetamine
- Levophacetoperane
- Liafensine
- LR-5182
- Manifaxine
- Mazindol
- Medifoxamine
- Mesocarb
- Metaphit
- MIN-117 (WF-516)
- Modafinil
- Nefopam
- Nomifensine
- NS-2359
- O-2172
- Oroxylin A
- Perafensine
- Pridefine
- Radafaxine
- Rimcazole
- Sertraline
- Sibutramine
- Tametraline
- Tedatioxetine
- Tripelennamine
- Venlafaxine
|
|
|
Enhancers |
|
|
Modulators |
|
|
- Antagonist-like
- SoRI-20041
|
|
|
|
VMATs |
- Inhibitors
- Amiodarone
- Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
- Bietaserpine
- Deserpidine
- Efavirenz
- GBR-12935
- Ibogaine
- Ketanserin
- Lobeline
- Reserpine
- Rose bengal
- Tetrabenazine
- Vanoxerine (GBR-12909)
|
|
|
|
Releasing agents
|
|
- Morpholines
- Fenbutrazate
- Fenmetramide
- Morazone
- Morforex
- Phendimetrazine
- Phenmetrazine
- Pseudophenmetrazine
|
|
- Oxazolines
- 4-MAR
- Aminorex
- Clominorex
- Cyclazodone
- Fenozolone
- Fluminorex
- Pemoline
- Thozalinone
|
|
- Phenethylamines (also amphetamines, cathinones, etc)
- 2-OH-PEA
- 4-CAB
- 4-FA
- 4-FMA
- 4-MA
- 4-MMA
- Alfetamine
- Amfecloral
- Amfepentorex
- Amfepramone
- Amphetamine (Dextroamphetamine
- Levoamphetamine)
- Amphetaminil
- β-Me-PEA
- BDB
- BOH
- Benzphetamine
- Buphedrone
- Bupropion
- Butylone
- Cathine
- Cathinone
- Clobenzorex
- Clortermine
- D-Deprenyl
- DMA
- DMMA
- Dimethylamphetamine
- Ephedrine
- Ethcathinone
- EBDB
- Ethylone
- Etilamfetamine
- Famprofazone
- Fenethylline
- Fenproporex
- Flephedrone
- Fludorex
- Furfenorex
- Hordenine
- 4-Hydroxyamphetamine
- Iofetamine (123I)
- Lophophine
- Mefenorex
- Mephedrone
- Metamfepramone
- Methamphetamine
- Dextromethamphetamine
- Levomethamphetamine
- Methcathinone
- Methedrone
- MMDA
- MMDMA
- MBDB
- MDA
- MDEA
- MDMA
- MDMPEA
- MDOH
- MDPEA
- Methylone
- Morforex
- Ortetamine
- pBA
- pCA
- pIA
- Pholedrine
- Phenethylamine
- Pholedrine
- Phenpromethamine
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Tiflorex
- Tyramine
- Xylopropamine
- Zylofuramine
|
|
- Piperazines
- 2C-B-BZP
- BZP
- MBZP
- MDBZP
- MeOPP
|
|
- Others
- 2-ADN
- 2-AI
- 2-AT
- 4-BP
- 5-APDI
- 5-IAI
- Clofenciclan
- Cyclopentamine
- Cypenamine
- Cyprodenate
- Feprosidnine
- Gilutensin
- Heptaminol
- Hexacyclonate
- Indanorex
- Isometheptene
- Methylhexanamine
- Naphthylaminopropane
- Octodrine
- Phthalimidopropiophenone
- Phenylbiguanide
- Propylhexedrine
- Levopropylhexedrine
- Tuaminoheptane
|
|
|
|
Enzyme inhibitors
|
|
PAH |
|
|
TH |
- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
|
|
AAAD |
- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
|
|
MAO |
- Nonselective
- Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine
|
|
- MAO-A selective
- Amiflamine
- Bazinaprine
- Befloxatone
- Brofaromine
- Cimoxatone
- Clorgiline
- CX157 (Tyrima)
- Eprobemide
- Esuprone
- Harmala alkaloids
- Methylene Blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
|
|
- MAO-B selective
- Almoxatone
- D-Deprenyl
- Ethanol
- Ladostigil
- Lazabemide
- Milacemide
- Nicotine
- Pargyline‡
- Rasagiline
- Safinamide
- Selegiline (L-Deprenyl)
|
|
|
COMT |
- Entacapone
- Nitecapone
- Tolcapone
|
|
DBH |
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Tropolone
|
|
|
|
Others
|
|
Precursors |
- L-Phenylalanine → L-Tyrosine → L-DOPA (levodopa)
|
|
Cofactors |
- Ferrous iron (Fe2+)
- Tetrahydrobiopterin
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
|
|
Neurotoxins |
- Amphetamine
- Methamphetamine
- MPP+
- MPTP
- Norsalsolinol
- Oxidopamine (6-OHDA)
- Rotenone
|
|
Others |
- Activity enhancers
- BPAP
- PPAP
|
|
- Levodopa prodrugs
- XP21279
|
|
- Others
- Bromantane (dopamine synthesis enhancer)
|
|
|
|
|
- See also:
- Adrenergics
- Melatonergics
- Serotonergics
- List of dopaminergic drugs
|
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- A Systematic Review and Network Meta-Analysis to Assess the Relative Efficacy of Antipsychotics for the Treatment of Positive and Negative Symptoms in Early-Onset Schizophrenia.
- Harvey RC1, James AC2, Shields GE3.
- CNS drugs.CNS Drugs.2016 Jan;30(1):27-39. doi: 10.1007/s40263-015-0308-1.
- INTRODUCTION: Early-onset schizophrenia (EOS) is a serious debilitating disorder with considerable morbidity and a reduced life expectancy; therefore, early diagnosis and effective treatments are particularly important. Negative symptoms are more prominent in adolescents and children (compared with
- PMID 26801655
- Reversibility of dopamine receptor antagonist-induced hyperprolactinemia and associated histological changes in Tg RasH2 wild-type mice.
- Krishna G1, Ganiger S2, Kannan K3, Gopalakrishnan G4, Goel S5.
- Reproductive toxicology (Elmsford, N.Y.).Reprod Toxicol.2015 Dec;58:73-8. doi: 10.1016/j.reprotox.2015.08.006. Epub 2015 Aug 29.
- The purpose of this study was to better understand the biological effects of increased prolactin levels induced in mice by dopamine D2 receptor antagonist molindone treatment. Toxicokinetics, prolactin levels, and reproductive tissue histology were evaluated in Tg rasH2 wild-type mice treated orally
- PMID 26327279
- Corrected QT changes during antipsychotic treatment of children and adolescents: a systematic review and meta-analysis of clinical trials.
- Jensen KG1, Juul K2, Fink-Jensen A3, Correll CU4, Pagsberg AK5.
- Journal of the American Academy of Child and Adolescent Psychiatry.J Am Acad Child Adolesc Psychiatry.2015 Jan;54(1):25-36. doi: 10.1016/j.jaac.2014.10.002. Epub 2014 Oct 16.
- OBJECTIVE: To evaluate the effect of antipsychotics on the corrected QT (QTc) interval in youth.METHOD: We searched PubMed (http://www.ncbi.nlm.nih.gov/pubmed) for randomized or open clinical trials of antipsychotics in youth <18 years with QTc data, meta-analyzing the results. Meta-regression a
- PMID 25524787
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