Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H23BrN2O3.ClH |
| Molecular Weight | 407.73 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN1CCC[C@H]1CNC(=O)C2=C(OC)C(Br)=CC=C2OC
InChI
InChIKey=WCPXLMIPGMFZMY-MERQFXBCSA-N
InChI=1S/C16H23BrN2O3.ClH/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);1H/t11-;/m0./s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11607043 | https://www.ncbi.nlm.nih.gov/pubmed/1981869
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11607043 | https://www.ncbi.nlm.nih.gov/pubmed/1981869
Remoxipride is a substituted benzamide. It is a weak, but relatively selective, central dopamine D2-receptor antagonist and appears to have preferential affinity for extrastriatal dopamine D2-receptors. It also has marked affinity for central sigma receptors. It was introduced by Astra (Roxiam) at the end of the eighties and was prescribed as an atypical antipsychotic. Remoxipride was withdrawn from the market worldwide by Astra because of several cases of aplastic anaemia associated with the drug.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 2.8 µM [IC50] | |||
Target ID: CHEMBL287 |
60.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ROXIAM Approved UseRemoxipride is primarily indicated in conditions like Schizophrenia, and can also be given in adjunctive therapy as an alternative drug of choice in Psychosis. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparison of the effects of haloperidol, remoxipride and raclopride on "pre"- and postsynaptic dopamine receptors in the rat brain. | 1988 Apr |
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| Hypotensive and bradycardic effects elicited by spinal dopamine receptor stimulation: effects of D1 and D2 receptor agonists and antagonists. | 1991 Oct |
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| Neuropsychopharmacological profile of remoxipride in comparison with clozapine. | 1997 Jan-Feb |
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| Role of dopamine D1 and D2 receptors in the micturition reflex in conscious rats. | 2001 |
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| Pharmacology of the atypical antipsychotic remoxipride, a dopamine D2 receptor antagonist. | 2001 Fall |
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| Psychosis in children: diagnosis and treatment. | 2001 Jun |
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| Antagonism of the discriminative stimulus effects of (+)-7-OH-DPAT by remoxipride but not PNU-99194A. | 2001 Mar |
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| Atypical antipsychotics: mechanism of action. | 2002 Feb |
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| Atypical kinetics for a series of putative dopamine antagonists to reverse the low-magnitude Ca2+ phase in the dopamine-bound D2short receptor state. | 2002 Jan |
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| Effects of antipsychotic drugs on operant responding after acute and repeated administration. | 2002 Mar |
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| Role of brain dopaminergic system in the adrenomedullin-induced diuresis and natriuresis. | 2003 Nov |
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| The effects of atypical antipsychotic medications on psychosocial outcomes. | 2003 Sep 1 |
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| Impact of atypical antipsychotics on quality of life in patients with schizophrenia. | 2004 |
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| Characterization of glutathione conjugates of the remoxipride hydroquinone metabolite NCQ-344 formed in vitro and detection following oxidation by human neutrophils. | 2004 Apr |
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| Anticonvulsant action of GBR-12909 and citalopram against acute experimentally induced limbic seizures. | 2004 Dec |
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| Anticonvulsant action of hippocampal dopamine and serotonin is independently mediated by D and 5-HT receptors. | 2004 May |
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| Development of behavioral sensitization to the cocaine-like fungicide triadimefon is prevented by AMPA, NMDa, DA D1 but not DA D2 receptor antagonists. | 2004 May |
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| XEDS-mapping for explaining release patterns from single pellets. | 2005 Feb 16 |
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| Dopaminergic mechanisms controlling urethral function in rats. | 2006 |
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| A dopaminergic deficit hypothesis of schizophrenia: the path to discovery. | 2006 |
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| Antipsychotic drugs inhibit the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells-an involvement of protein kinases. | 2006 Apr |
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| Activation of D2-like receptors induces sympathetic climactic-like responses in male and female anaesthetised rats. | 2006 Jun |
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| D2 dopamine receptor blockade prevents cognitive effects of Ang IV and des-Phe6 Ang IV. | 2006 Jun 15 |
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| Prototypical antipsychotic drugs protect hippocampal neuronal cultures against cell death induced by growth medium deprivation. | 2006 Mar 30 |
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| Quality of life in the long-term treatment and the role of second-generation antipsychotics. | 2007 Feb |
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| Thioridazine for schizophrenia. | 2007 Jul 18 |
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| Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys. | 2009 Nov 5 |
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| Comparison of the agonist-antagonist interaction model and the pool model for the effect of remoxipride on prolactin. | 2010 Dec |
|
| Tolerability of zotepine in Indian patients: Preliminary experience. | 2010 Jul |
|
| Zotepine versus other atypical antipsychotics for schizophrenia. | 2010 Oct 6 |
Patents
Sample Use Guides
Two hundred and forty-two patients with acute schizophrenia were enrolled in a double-blind, comparative, dose-finding study of a novel antipsychotic, remoxipride. Remoxipride was evaluated in a low (30 to 90 mg), medium (120 to 240 mg) and a high (300 to 600 mg) dose range and compared with a haloperidol (15 to 45 mg), which was administered to a similar group of patients. The results support the antipsychotic effect of remoxipride, with maximum efficacy occurring at daily doses between 120 mg and 600 mg.
A controlled release (CR) formulation of remoxipride (Roxiam(®), Astra) given once-daily was compared to immediate release (IR) remoxipride given twice-daily, with respect to efficacy and tolerability, in a 4-week multicentre parallel-group dose titration (200-600 mg/day) study with acutely ill schizophrenic patients. Forty- three patients received remoxipride CR (mean dose 344 mg/day) and 49 patients received remoxipride IR (mean dose 346 mg/day).
Route of Administration:
Oral
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QS4S72U30K
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m9522
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73220-03-8
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15565709
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ACTIVE MOIETY
SUBSTANCE RECORD
