Remoxipride: Difference between revisions

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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Legal status	Withdrawn;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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VisualWikitext

Latest revision as of 14:16, 13 April 2015

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typical antipsychotic) which was previously used in Europe for the treatment of schizophrenia and acute mania but was withdrawn due to toxicity concerns (incidence of aplastic anemia in 1/10,000 patients).^[2] It was initially launched by AstraZeneca in 1990 and suspension of its use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

@@ Line 1: / Line 1: @@
-{{drugbox
+{{Drugbox
-| IUPAC_name        = 3-Bromo-N-[ [(''2S'')-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxy-benzamide
+| Verifiedfields = changed
-| image             = Remoxipride.png
+| verifiedrevid = 464380815
-| CAS_number        = 117591-79-4
+| IUPAC_name = (''S'')-3-bromo-''N''-[(1-ethylpyrrolidin-2-yl)methyl]-2,6-dimethoxy-benzamide
-| ATC_prefix        = N05
+| image =Remoxipride Structural Formulae.png
-| ATC_suffix        = AL04
-| PubChem           = 54477
+<!--Clinical data-->
-| DrugBank          =
+| tradename = Roxiam
-| chemical_formula  =
+| pregnancy_category =
-| molecular_weight  = 371.27 g/mol
+| legal_status = Withdrawn
-| bioavailability   = C<sub>16</sub>H<sub>23</sub>BrN<sub>2</sub>O<sub>3</sub>
+| routes_of_administration = Oral
-| protein_bound     =
-| metabolism        =
+<!--Pharmacokinetic data-->
-| elimination_half-life =
+| bioavailability = 96%<ref name = PK>{{cite journal|title=Remoxipride - a new potential antipsychotic compound: tolerability and pharmacokinetics after single oral and intravenous administration in healthy male volunteers|journal=Psychopharmacology|author=Grind, M; Nilsson, MI; Nilsson, L; Oxenstierna, G; Sedvall, G; Wahlén, A|date=1989|volume=98|issue=3|page=304-309|pmid=2568653|doi=10.1007/bf00451679}}</ref>
-| excretion         =
+| protein_bound = 89-98%
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
+| metabolism = [[Hepatic]]<ref name = PK/>
-| pregnancy_category=
+| elimination_half-life = 4-7 hours<ref name = PK/>
-| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
+| excretion = [[Renal]]<ref name = PK/>
-| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
+<!--Identifiers-->
-| legal_US          =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
+| CAS_number_Ref = {{cascite|changed|??}}
-| legal_status      =
+| CAS_number = 117591-79-4
-| routes_of_administration =
+| ATC_prefix = N05
+| ATC_suffix = AL04
+| PubChem = 54477
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank = DB00409
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 49195
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 0223RD59PE
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D02683
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 22242
+<!--Chemical data-->
+| C=16 | H=23 | Br=1 | N=2 | O=3
+| molecular_weight = 371.27 g/mol
+| smiles = CCN2CCC[C@H]2CNC(=O)c1c(OC)ccc(Br)c1OC
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 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
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = GUJRSXAPGDDABA-NSHDSACASA-N
 }}
+__Notoc__
+{{SI}}
+{{CMG}}
+==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).<ref name="isbn3-527-31058-4">{{cite book | author = José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens | title = Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application | publisher = Wiley-VCH | location = Weinheim | year = 2007 | pages = | isbn = 3-527-31058-4 | oclc = | doi = | accessdate = }}</ref> It was initially launched by [[AstraZeneca]] in 1990 and suspension of its use began in 1993.<ref name="isbn3-527-31058-4">{{cite book | author = José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens | title = Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application | publisher = Wiley-VCH | location = Weinheim | year = 2007 | pages = | isbn = 3-527-31058-4 | oclc = | doi = | accessdate = }}</ref> Remoxipride acts as a [[binding selectivity|selective]] [[D2 receptor|D<sub>2</sub>]] and [[D3 receptor|D<sub>3</sub> receptor]] [[receptor antagonist|antagonist]] and also has high [[affinity (pharmacology)|affinity]] for the [[sigma receptor]], possibly playing a role in its atypical neuroleptic action.<ref name="pmid1978484">{{cite journal | author = Köhler C, Hall H, Magnusson O, Lewander T, Gustafsson K | title = Biochemical pharmacology of the atypical neuroleptic remoxipride | journal = Acta Psychiatrica Scandinavica. Supplementum | volume = 358 | issue = | pages = 27–36 | year = 1990 | pmid = 1978484 | doi = | url = }}</ref>
-'''Remoxipride''' is a substituted [[benzamide]] which was a promising [[antipsychotic]] during clinical trials in the 1990s, but was removed due to possible side effects.
+Due to its short half-life twice daily (bid) dosing is required, although a once-daily controlled-release tablet has been developed.<ref name = dose>{{cite journal|title=Once-daily controlled release remoxipride is equieffective with twice-daily immediate release remoxipride in the treatment of schizophrenia|author=Alexander, MS; Chakravarti, SK; Sundararajan, K; Mullin, JM; Shaw, SH; Blomqvist, M; Lockett, CM|journal=Journal of Psychopharmacology|date=January 1993|volume=7|issue=3|doi=10.1177/026988119300700307|page=276-82|pmid=22290842}}</ref> There was some interest in its use in the treatment of treatment-resistant schizophrenia.<ref name = TRS>{{cite journal|title=Remoxipride therapy in treatment resistant schizophrenia|author=Conley, R; Dixon, L; An Nguyen, R; Taminga, C; Hain, R|doi=10.1016/0920-9964(93)90521-J|date=April 1993|volume=9|issue=2-3|journal=Schizophrenia Research|page=235-236}}</ref><ref name = TRS2>{{cite journal|title=Remoxipride therapy in poorly responsive schizophrenics|author=Conley, R; Dixon, L; An Nguyen, R; Taminga, C; Raymond, R|doi=10.1016/0920-9964(91)90208-9|date=April 1993|volume=4|issue=3|page=316|journal=Schizophrenia Research}}</ref>
-== Clinical trials ==
+== See also ==
-Remoxipride is a selective [[Dopamine receptor|D2]] [[Receptor antagonist|antagonist]], with a relatively low effective dosage and low incidence of side effects relative to [[haloperidol]]. However, after its introduction in Europe, its use was correlated with incidence of [[aplastic anemia]] in as many as 1 in 10,000 cases, and it was taken off the market until its relationship to this possible side effect could be studied.
+* [[Typical antipsychotic]]
+* [[Benzamide]]
+== References ==
+{{Reflist|2}}
 == External links ==
 * [http://www.acnp.org/G4/GN401000123/CH121.html Herbert Y. Meltzer, Atypical Antipsychotic Drugs, 2000]
+{{Antipsychotics}}
+{{Dopaminergics}}
+{{Sigmaergics}}
 [[Category:Atypical antipsychotics]]
-[[Category:Amides]]
+[[Category:Pyrrolidines]]
+[[Category:Benzamides]]
-{{pharma-stub}}
+[[Category:Phenol ethers]]
+[[Category:Organobromides]]
+[[Category:Withdrawn drugs]]
-[[de:Remoxiprid]]
+[[Category:Drug]]

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

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)

Remoxipride: Difference between revisions

Latest revision as of 14:16, 13 April 2015

Overview

See also

References

External links

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