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Remoxipride - Wikipedia

From Wikipedia, the free encyclopedia

Remoxipride
Clinical data

Trade names	Roxiam
Routes of administration	Oral
ATC code	N05AL04 (WHO)
Legal status
Legal status	Withdrawn
Pharmacokinetic data
Bioavailability	96%^[1]
Protein binding	89-98%
Metabolism	Hepatic^[1]
Elimination half-life	4-7 hours^[1]
Excretion	Renal^[1]
Identifiers
IUPAC name 3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxybenzamide
CAS Number	80125-14-0^N
PubChem CID	54477
DrugBank	DB00409^Y
ChemSpider	49195^Y
UNII	0223RD59PE
KEGG	D02683^Y
ChEMBL	ChEMBL22242^Y
CompTox Dashboard (EPA)	DTXSID6045668
Chemical and physical data
Formula	C₁₆H₂₃BrN₂O₃
Molar mass	371.275 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN2CCC[C@H]2CNC(=O)c1c(OC)ccc(Br)c1OC
InChI InChI=1S/C16H23BrN2O3/c1-4-19-9-5-6-11(19)10-18-16(20)14-13(21-2)8-7-12(17)15(14)22-3/h7-8,11H,4-6,9-10H2,1-3H3,(H,18,20)/t11-/m0/s1^Y Key:GUJRSXAPGDDABA-NSHDSACASA-N^Y
^NY (what is this?) (verify)

Remoxipride (Roxiam) is an atypical antipsychotic (although according to some sources it is a typical antipsychotic) which was previously used in Europe for the treatment of schizophrenia and acute mania but was withdrawn due to toxicity concerns (incidence of aplastic anemia in 1/10,000 patients).^[2] It was initially launched by AstraZeneca in 1990 and suspension of its use began in 1993.^[2] Remoxipride acts as a selective D₂ and D₃ receptor antagonist and also has high affinity for the sigma receptor, possibly playing a role in its atypical neuroleptic action.^[3]

Due to its short half-life twice daily (bid) dosing is required, although a once-daily controlled-release tablet has been developed.^[4] There was some interest in its use in the treatment of treatment-resistant schizophrenia.^[5]^[6]

References

^ ^a ^b ^c ^d Grind M, Nilsson MI, Nilsson L, Oxenstierna G, Sedvall G, Wahlén A (1989). "Remoxipride--a new potential antipsychotic compound. Tolerability and pharmacokinetics after single oral and intravenous administration in healthy male volunteers". Psychopharmacology. 98 (3): 304–9. doi:10.1007/bf00451679. PMID 2568653. S2CID 27357548.
^ ^a ^b Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 978-3-527-31058-6.
^ Köhler C, Hall H, Magnusson O, Lewander T, Gustafsson K (1990). "Biochemical pharmacology of the atypical neuroleptic remoxipride". Acta Psychiatrica Scandinavica. Supplementum. 358: 27–36. doi:10.1111/j.1600-0447.1990.tb05282.x. PMID 1978484. S2CID 144567193.
^ Alexander MS, Chakravarti SK, Sundararajan K, Mullin JM, Shaw SH, Blomqvist M, Lockett CM (January 1993). "Once-daily controlled release remoxipride is equieffective with twice-daily immediate release remoxipride in the treatment of schizophrenia". Journal of Psychopharmacology. 7 (3): 276–82. doi:10.1177/026988119300700307. PMID 22290842. S2CID 23518319.
^ Conley R, Dixon L, Nguyen JA, Tamminga C, Raymond R (April 1993). "Remoxipride therapy in treatment resistant schizophrenia". Schizophrenia Research. 9 (2–3): 235–236. doi:10.1016/0920-9964(93)90521-J. S2CID 54386181.
^ Conley R, Dixon L, Nguyen JA, Tamminga C, Raymond R (April 1993). "Remoxipride therapy in poorly responsive schizophrenics". Schizophrenia Research. 4 (3): 316. doi:10.1016/0920-9964(91)90208-9. S2CID 54317014.

External links

Herbert Y. Meltzer, Atypical Antipsychotic Drugs, 2000 Archived 2006-04-26 at the Wayback Machine

v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol Xanomeline/trospium chloride
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Dopamine receptor modulators

D₁-like

Agonists	Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines: Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives: A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines: BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others: A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs^{[clarification needed]}	Tetrahydroisoquinolines: DETQ DPTQ Mevidalen
Antagonists	Typical antipsychotics: Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics: Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others: Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390

D₂-like

Agonists

Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine)
Dopexamine
Etilevodopa
Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
Melevodopa
XP21279

Atypical antipsychotics: Alentemol (U-66444B)
Aripiprazole (+sertraline)
Aripiprazole lauroxil
Bifeprunox
Brexpiprazole
Brilaroxazine
Cariprazine
F-15063
Lumateperone
Norclozapine

Antagonists

Typical antipsychotics: Acepromazine
Acetophenazine
Azaperone
Benperidol
Bromperidol
Butaclamol
Butaperazine
Chloracizine
Chlorproethazine
Chlorpromazine
Chlorprothixene
Ciclindole
Clopenthixol
Clothixamide
Clopimozide
Droperidol
Fluacizine
Fluanisone
Flucindole
Fluotracen
Flupentixol (flupenthixol) (+melitracen)
Fluphenazine
Fluprothixene
Fluspirilene
Haloperidol
Homopipramol
Lenperone
Levomepromazine (methotrimeprazine)
Levosulpiride
Loxapine
Mesoridazine
Moperone
Naranol
Nemonapride
Penfluridol
Perathiepin
Perazine
Pericyazine (periciazine)
Perphenazine (+amitriptyline)
Piflutixol (pifluthixol)
Pimozide
Pipamperone
Preclamol
Prochlorperazine
Promazine
Prothipendyl
Spiperone (spiroperidol)
Sulforidazine
Sulpiride
Sultopride
Teflutixol
Thiopropazate
Thioproperazine
Thioridazine
Thiothixene
Timiperone
Trifluoperazine (+tranylcypromine)
Triflupromazine
Trifluperidol
Zetidoline
Zuclopenthixol

Antiemetics/gastroprokinetics/sedatives: Aceprometazine
AS-8112
Alimemazine
Alizapride
Benzquinamide
Bromopride
Clebopride
Deudomperidone
Domperidone
Eticlopride
Hydroxyzine
Itopride
Metoclopramide
Metopimazine
Promethazine
Thiethylperazine
Trazpiroben
Trimethobenzamide

See also: Receptor/signaling modulators
Adrenergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

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