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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014553
Secondary Accession Numbers
  • HMDB14553
Metabolite Identification
Common NameRemoxipride
DescriptionRemoxipride is only found in individuals that have used or taken this drug. It is an antipsychotic agent that is specific for dopamine D2 receptors. It has been shown to be effective in the treatment of schizophrenia. [PubChem]Remoxipride acts as an antagonist at the D2 dopamine receptor. It is believed that overactivity of dopamine systems in the mesolimbic pathway may contribute to the "positive symptoms" of schizophrenia (such as delusions and hallucinations), whereas problems with dopamine function in the mesocortical pathway may be responsible for the "negative symptoms", such as avolition, flat emotional response and alogia. Therefore, by decreasing the levels of dopamine in these pathways, it is thought that remoxipride is able to reduce the symptoms of schizophrenia, particularily the "positive symptoms".
Structure
Data?1582753192
Synonyms
ValueSource
FLA-731RoxiamHMDB
a-33547REmoxiprideHMDB
RomoxiprideHMDB
FLA-731HMDB
Monohydrochloride, remoxiprideHMDB
Remoxipride hydrochlorideHMDB
Remoxipride monohydrochloride monohydrateHMDB
(S)-3-Bromo-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dimethoxybenzamideHMDB
Hydrochloride anhydrous, remoxiprideHMDB
Remoxipride monohydrochlorideHMDB
Remoxipride monohydrochloride, (R)-isomerHMDB
Remoxipride, (R)-isomerHMDB
Remoxipride hydrochloride anhydrousHMDB
Anhydrous, remoxipride hydrochlorideHMDB
Hydrochloride, remoxiprideHMDB
Monohydrochloride monohydrate, remoxiprideHMDB
Chemical FormulaC16H23BrN2O3
Average Molecular Weight371.269
Monoisotopic Molecular Weight370.089205259
IUPAC Name3-bromo-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,6-dimethoxybenzamide
Traditional Nameremoxipride
CAS Registry Number80125-14-0
SMILES
CCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC
InChI Identifier
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
InChI KeyGUJRSXAPGDDABA-NSHDSACASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Halobenzene
  • Bromobenzene
  • Aryl bromide
  • Aryl halide
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organobromide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.13 g/LNot Available
LogP2.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.94ALOGPS
logP2.34ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.06ChemAxon
pKa (Strongest Basic)8.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.8 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.56 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+169.53730932474
DeepCCS[M-H]-167.17930932474
DeepCCS[M-2H]-200.06530932474
DeepCCS[M+Na]+175.6330932474
AllCCS[M+H]+181.532859911
AllCCS[M+H-H2O]+178.632859911
AllCCS[M+NH4]+184.232859911
AllCCS[M+Na]+185.032859911
AllCCS[M-H]-180.432859911
AllCCS[M+Na-2H]-181.132859911
AllCCS[M+HCOO]-182.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RemoxiprideCCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC3376.3Standard polar33892256
RemoxiprideCCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC2619.5Standard non polar33892256
RemoxiprideCCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC2515.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Remoxipride,1TMS,isomer #1CCN1CCC[C@H]1CN(C(=O)C1=C(OC)C=CC(Br)=C1OC)[Si](C)(C)C2639.4Semi standard non polar33892256
Remoxipride,1TMS,isomer #1CCN1CCC[C@H]1CN(C(=O)C1=C(OC)C=CC(Br)=C1OC)[Si](C)(C)C2523.8Standard non polar33892256
Remoxipride,1TMS,isomer #1CCN1CCC[C@H]1CN(C(=O)C1=C(OC)C=CC(Br)=C1OC)[Si](C)(C)C3423.2Standard polar33892256
Remoxipride,1TBDMS,isomer #1CCN1CCC[C@H]1CN(C(=O)C1=C(OC)C=CC(Br)=C1OC)[Si](C)(C)C(C)(C)C2867.1Semi standard non polar33892256
Remoxipride,1TBDMS,isomer #1CCN1CCC[C@H]1CN(C(=O)C1=C(OC)C=CC(Br)=C1OC)[Si](C)(C)C(C)(C)C2718.8Standard non polar33892256
Remoxipride,1TBDMS,isomer #1CCN1CCC[C@H]1CN(C(=O)C1=C(OC)C=CC(Br)=C1OC)[Si](C)(C)C(C)(C)C3492.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Remoxipride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9021000000-9daaecbf42f2128e1ad42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Remoxipride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 10V, Positive-QTOFsplash10-00di-0519000000-3d2acd15eff0b46d38f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 20V, Positive-QTOFsplash10-03di-3912000000-e22b0c0384636903281f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 40V, Positive-QTOFsplash10-01qc-9110000000-0ddfc4805450139713b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 10V, Negative-QTOFsplash10-014i-0029000000-cd8c03d7ed0101f27c5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 20V, Negative-QTOFsplash10-03di-0294000000-26c857c4f2362cbb32312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 40V, Negative-QTOFsplash10-06r6-9671000000-9edffc6cb1f1ba0b83f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 10V, Positive-QTOFsplash10-00di-0019000000-1785aaf5dd85924ca1a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 20V, Positive-QTOFsplash10-00di-1329000000-f2461d27117d29c1a1372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 40V, Positive-QTOFsplash10-01oy-5790000000-c002f172028926a46b442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 10V, Negative-QTOFsplash10-014i-0029000000-b9eb29b968cffb6427c72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 20V, Negative-QTOFsplash10-014i-3189000000-e1209bfcec679b8827472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Remoxipride 40V, Negative-QTOFsplash10-0fbc-9072000000-004d419109fc829dd6cb2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00409 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00409 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00409
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID49195
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRemoxipride
METLIN IDNot Available
PubChem Compound54477
PDB IDNot Available
ChEBI ID127616
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
  2. Lang AE, Sandor P, Duff J: Remoxipride in Parkinson's disease: differential response in patients with dyskinesias fluctuations versus psychosis. Clin Neuropharmacol. 1995 Feb;18(1):39-45. [PubMed:8665533 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
References
  1. Seeman P, Corbett R, Van Tol HH: Atypical neuroleptics have low affinity for dopamine D2 receptors or are selective for D4 receptors. Neuropsychopharmacology. 1997 Feb;16(2):93-110; discussion 111-35. [PubMed:9015795 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Seeman P, Corbett R, Van Tol HH: Atypical neuroleptics have low affinity for dopamine D2 receptors or are selective for D4 receptors. Neuropsychopharmacology. 1997 Feb;16(2):93-110; discussion 111-35. [PubMed:9015795 ]
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration
Gene Name:
SIGMAR1
Uniprot ID:
Q99720
Molecular weight:
25127.5
References
  1. Lang A, Soosaar A, Koks S, Volke V, Bourin M, Bradwejn J, Vasar E: Pharmacological comparison of antipsychotic drugs and sigma-antagonists in rodents. Pharmacol Toxicol. 1994 Sep-Oct;75(3-4):222-7. [PubMed:7800667 ]
  2. Okuyama S: [Atypical antipsychotic profiles of sigma receptor ligands]. Nihon Yakurigaku Zasshi. 1999 Jul;114(1):13-23. [PubMed:10562961 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
Gene Name:
DRD3
Uniprot ID:
P35462
Molecular weight:
44224.3
References
  1. Christian AJ, Goodwin AK, Baker LE: Antagonism of the discriminative stimulus effects of (+)-7-OH-DPAT by remoxipride but not PNU-99194A. Pharmacol Biochem Behav. 2001 Mar;68(3):371-7. [PubMed:11325388 ]