Remoxipride

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Remoxipride
Clinical data
Trade names	Roxiam
Routes of; administration	Oral
ATC code	N05AL04 (WHO) ;
Legal status
Legal status	Withdrawn;
Pharmacokinetic data
Bioavailability	96%
Protein binding	89-98%
Metabolism	Hepatic
Elimination half-life	4-7 hours
Excretion	Renal
Identifiers
	IUPAC name (S)-3-bromo-N-[(1-ethylpyrrolidin-2-yl)methyl]-2,6-dimethoxy-benzamide;
CAS Number	117591-79-4 ;
PubChem CID	54477;
DrugBank	DB00409 ;
ChemSpider	49195 ;
UNII	0223RD59PE;
KEGG	D02683 ;
ChEMBL	ChEMBL22242 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C16H23BrN2O3
Molar mass	371.27 g/mol
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 ; Key:GUJRSXAPGDDABA-NSHDSACASA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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a typical antipsychotic) which was previously used in Europe for the treatment of schizophrenia and acute mania but was withdrawn due to toxicity concerns (incidence of aplastic anemia in 1/10,000 patients).^[2] It was initially launched by AstraZeneca in 1990 and suspension of its use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

↑ ^1.0 ^1.1 ^1.2 ^1.3 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): 304-309. doi:10.1007/bf00451679. PMID 2568653.
↑ ^2.0 ^2.1 José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 3-527-31058-4.
↑ 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. PMID 1978484.
↑ 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.
↑ Conley, R; Dixon, L; An Nguyen, R; Taminga, C; Hain, R (April 1993). "Remoxipride therapy in treatment resistant schizophrenia". Schizophrenia Research. 9 (2–3): 235-236. doi:10.1016/0920-9964(93)90521-J.
↑ Conley, R; Dixon, L; An Nguyen, R; Taminga, C; Raymond, R (April 1993). "Remoxipride therapy in poorly responsive schizophrenics". Schizophrenia Research. 4 (3): 316. doi:10.1016/0920-9964(91)90208-9.

External links

Herbert Y. Meltzer, Atypical Antipsychotic Drugs, 2000

Template:Sigmaergics

[PK-1] 1.0 ^1.1 ^1.2 ^1.3 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): 304-309. doi:10.1007/bf00451679. PMID 2568653.

[isbn3-527-31058-4-2] 2.0 ^2.1 José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 3-527-31058-4.

[pmid1978484-3] 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. PMID 1978484.

[dose-4] 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.

[TRS-5] Conley, R; Dixon, L; An Nguyen, R; Taminga, C; Hain, R (April 1993). "Remoxipride therapy in treatment resistant schizophrenia". Schizophrenia Research. 9 (2–3): 235-236. doi:10.1016/0920-9964(93)90521-J.

[TRS2-6] Conley, R; Dixon, L; An Nguyen, R; Taminga, C; Raymond, R (April 1993). "Remoxipride therapy in poorly responsive schizophrenics". Schizophrenia Research. 4 (3): 316. doi:10.1016/0920-9964(91)90208-9.

[1]

[2]

[3]

[4]

[5]

[6]

v t e Antipsychotics (neuroleptics) (N05A)
Typical	Benzamides: Levosulpiride • Nemonapride • Sulpiride • Sultopride • Tiapride • Veralipride; Butyrophenones: 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 • Piperacetazine • Pipotiazine • Prochlorperazine • Promazine • Promethazine • Propiomazine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioproperazine • Thioridazine • Trifluoperazine • Triflupromazine; Thioxanthenes: Chlorprothixene • Clopenthixol • Flupentixol • Thiothixene • Zuclopenthixol; Tricyclics: Amoxapine • Butaclamol • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin • Trimipramine; Others: Prothipendyl
Atypical	Benzamides: Amisulpride • Remoxipride; Butyrophenones: Cinuperone • Setoperone; Benzo(iso)oxazole piperidines: Iloperidone • Ocaperidone • Paliperidone • Risperidone; Benzo(iso)thiazole piperazines: Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone; Diphenylbutylpiperazines: Amperozide; Phenylpiperazines: Aripiprazole • Bifeprunox • Elopiprazole • Umespirone; Tricyclics: Asenapine • Carpipramine • Clocapramine • Clotiapine • Clozapine • Fluperlapine • Gevotroline • Metitepine/Methiothepin • Mosapramine • NDMC • Olanzapine • Piquindone • Quetiapine • Tenilapine • Zotepine; Others: Blonanserin • Cariprazine • Molindone • Pimavanserin • Roxindole • Sarizotan • Sertindole • Spiramide
Others	Azacyclonol • Cannabidiol • D-Cycloserine • Lithium • Mifepristone • Oxypertine • Reserpine • Rimcazole • Secretin • Talnetant • Tetrabenazine • Vabicaserin
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III Template:Psychology navs

Remoxipride

Overview

See also

References

External links

Navigation menu

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 (S)-3-bromo-N-[(1-ethylpyrrolidin-2-yl)methyl]-2,6-dimethoxy-benzamide
CAS Number	117591-79-4^N
PubChem CID	54477
DrugBank	DB00409^Y
ChemSpider	49195^Y
UNII	0223RD59PE
KEGG	D02683^Y
ChEMBL	ChEMBL22242^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₆H₂₃BrN₂O₃
Molar mass	371.27 g/mol
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)