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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Legal status	Withdrawn;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 3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxybenzamide;
CAS Number	80125-14-0 ;
PubChem CID	54477;
DrugBank	DB00409 ;
ChemSpider	49195 ;
UNII	0223RD59PE;
KEGG	D02683 ;
ChEMBL	ChEMBL22242 ;
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 ; Key:GUJRSXAPGDDABA-NSHDSACASA-N ;
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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a typical antipsychotic) which was previously used in Europe for the treatment of schizophrenia and acute mania but was withdrawn due to toxicity concerns (incidence of aplastic anemia in 1/10,000 patients).^[2] It was initially launched by AstraZeneca in 1990 and suspension of its use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.