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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C16H23BrN2O3 |
| Molecular Weight | 371.269 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 Remoxipride was withdrawn from the market worldwide by Astra because of several cases of aplastic anaemia associated with the drug.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 |
|---|---|---|
| Remoxipride, a new potential antipsychotic compound with selective antidopaminergic actions in the rat brain. | 1984 Jul 20 |
|
| Comparison of the effects of haloperidol, remoxipride and raclopride on "pre"- and postsynaptic dopamine receptors in the rat brain. | 1988 Apr |
|
| Cognitive disturbances in neuroleptic therapy. | 1990 |
|
| Hypotensive and bradycardic effects elicited by spinal dopamine receptor stimulation: effects of D1 and D2 receptor agonists and antagonists. | 1991 Oct |
|
| Concentrations of remoxipride and its phenolic metabolites in rat brain and plasma. Relationship to extrapyramidal side effects and atypical antipsychotic profile. | 1993 |
|
| Effects of dopamine D1 and D2 receptor agonists and antagonists on seizures induced by chemoconvulsants in mice. | 1993 Apr-May |
|
| Aplastic anaemia and remoxipride. | 1993 Nov 13 |
|
| Conformationally restricted analogues of remoxipride as potential antipsychotic agents. | 1993 Oct 29 |
|
| The tolerability and efficacy of the atypical neuroleptic remoxipride compared with clozapine and haloperidol in acute schizophrenia. | 1994 |
|
| Psychomotor impairment and cognitive disturbances induced by neuroleptics. | 1994 |
|
| Symptomatic relief from treatment-induced psychosis in Parkinson's disease: an open-label pilot study with remoxipride. | 1994 Mar |
|
| Remoxipride in the treatment of psychoses. | 1994 May |
|
| Remoxipride in Parkinson's disease: differential response in patients with dyskinesias fluctuations versus psychosis. | 1995 Feb |
|
| Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine. | 1995 Sep 5 |
|
| Remoxipride in the treatment of levodopa-induced psychosis. | 1996 Oct |
|
| Neuropsychopharmacological profile of remoxipride in comparison with clozapine. | 1997 Jan-Feb |
|
| Psychosis in children: diagnosis and treatment. | 2001 Jun |
|
| Anticonvulsant action of GBR-12909 and citalopram against acute experimentally induced limbic seizures. | 2004 Dec |
|
| XEDS-mapping for explaining release patterns from single pellets. | 2005 Feb 16 |
|
| Studies on the effect of MDMA ('ecstasy') on the body temperature of rats housed at different ambient room temperatures. | 2005 Sep |
|
| Dopaminergic mechanisms controlling urethral function in rats. | 2006 |
|
| A dopaminergic deficit hypothesis of schizophrenia: the path to discovery. | 2006 |
|
| Antipsychotic drugs inhibit the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells-an involvement of protein kinases. | 2006 Apr |
|
| Cocaine strongly reduces prepulse inhibition in apomorphine-susceptible rats, but not in apomorphine-unsusceptible rats: regulation by dopamine D2 receptors. | 2006 Dec 15 |
|
| Antipsychotic medication for elderly people with schizophrenia. | 2006 Jan 25 |
|
| Inhibitory effect of antipsychotic drugs on the Con A- and LPS-induced proliferative activity of mouse splenocytes: a possible mechanism of action. | 2006 Jun |
|
| Activation of D2-like receptors induces sympathetic climactic-like responses in male and female anaesthetised rats. | 2006 Jun |
|
| D2 dopamine receptor blockade prevents cognitive effects of Ang IV and des-Phe6 Ang IV. | 2006 Jun 15 |
|
| Prototypical antipsychotic drugs protect hippocampal neuronal cultures against cell death induced by growth medium deprivation. | 2006 Mar 30 |
|
| Dopamine D2 and D3 receptors in human putamen, caudate nucleus, and globus pallidus. | 2006 Sep 1 |
|
| Sigma 1 receptor-mediated increase in hippocampal extracellular dopamine contributes to the mechanism of the anticonvulsant action of neuropeptide Y. | 2007 Dec |
|
| Quality of life in the long-term treatment and the role of second-generation antipsychotics. | 2007 Feb |
|
| Differences in the cellular mechanism underlying the effects of amphetamine on prepulse inhibition in apomorphine-susceptible and apomorphine-unsusceptible rats. | 2007 Jan |
|
| Thioridazine for schizophrenia. | 2007 Jul 18 |
|
| Evaluation of osmotic effects on coated pellets using a mechanistic model. | 2007 May 4 |
|
| NMDA-mediated release of glutamate and GABA in the subthalamic nucleus is mediated by dopamine: an in vivo microdialysis study in rats. | 2007 Nov |
|
| Psilocybin-induced stimulus control in the rat. | 2007 Oct |
|
| Effectiveness of second generation antipsychotics: a systematic review of randomized trials. | 2008 Apr 25 |
|
| Mechanistic model for drug release during the lag phase from pellets coated with a semi-permeable membrane. | 2008 Apr 7 |
|
| Therapeutic drug monitoring of seven psychotropic drugs and four metabolites in human plasma by HPLC-MS. | 2009 Dec 5 |
|
| FemtoMolar measurements using accelerator mass spectrometry. | 2009 Mar |
|
| Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys. | 2009 Nov 5 |
|
| Online solid phase extraction with liquid chromatography-tandem mass spectrometry to analyze remoxipride in small plasma-, brain homogenate-, and brain microdialysate samples. | 2010 Apr 15 |
|
| Dissociable neural systems for timing: evidence from subjects with basal ganglia lesions. | 2010 Apr 23 |
|
| 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 |
|
| Participation of D 1-4 dopamine receptors in the pro-cognitive effects of angiotensin IV and des-Phe 6 angiotensin IV. | 2010 Mar |
|
| Memory encoding and dopamine in the aging brain: a psychopharmacological neuroimaging study. | 2010 Mar |
|
| Zotepine versus other atypical antipsychotics for schizophrenia. | 2010 Oct 6 |
|
| Locomotor response to L-DOPA in reserpine-treated rats following central inhibition of aromatic L-amino acid decarboxylase: further evidence for non-dopaminergic actions of L-DOPA and its metabolites. | 2010 Sep |
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
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
QS4S72U30K
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| Record Status |
Validated (UNII)
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| Record Version |
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