3-bromo-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,6-dimethoxybenzamide

• ChemBase ID: 292
• Molecular Formular: C16H23BrN2O3
• Molecular Mass: 371.26942
• Monoisotopic Mass: 370.08920461
• SMILES: Brc1c(OC)c(C(=O)NC[C@H]2N(CCC2)CC)c(OC)cc1
• Canonical SMILES: CCN1CCC[C@H]1CNC(=O)c1c(OC)ccc(c1OC)Br
• 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
• InChIKey: GUJRSXAPGDDABA-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-bromo-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,6-dimethoxybenzamide
• IUPAC Traditional name: remoxipride
• Synonyms: Remoxiprida [INN-Spanish]; Remoxipride [Usan:Ban:Inn]; Remoxipridum [INN-Latin]; Romoxipride; Remoxipride; (S)-3-BroMo-N-((1-ethylpyrrolidin-2-yl)Methyl)-2,6-diMethoxybenzaMide

Database IDs

• CAS Number: 80125-14-0
• PubChem SID: 46508689; 160963755
• PubChem CID: 54477

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.061707
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.46103975
• LogD (pH = 7.4): 1.3025001
• Log P: 2.3419893
• Molar Refractivity: 90.5612 cm^3
• Polarizability: 34.70597 Å^3
• Polar Surface Area: 50.8 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.94
• LOG S: -3.47
• Solubility (Water): 1.27e-01 g/l

PROPERTIES

Physical Property

• Solubility: 74 mg/L
• Hydrophobicity(logP): 2.9

Product Information

• Purity: 97%

DETAILS

DrugBank - DB00409

• Drug Groups: approved; withdrawn
• Description: An antipsychotic agent that is specific for dopamine D2 receptors. It has been shown to be effective in the treatment of schizophrenia. [PubChem]
• Indication: Remoxipride is an atypical antipsychotic once used for the treatment of schizophrenia.
• Pharmacology: Remoxipride, a substituted benzamide, is a selective D2 receptor antagonist. It has been shown to be effective in the treatment of schizophrenia. Some antipsychotics block domapinergic receptors as well as cholinergic, noradrenergic and histaminergic receptors. Remoxipride was developed to act specifically on the dopamine D2 receptor. As a consequence, several undesired side effects can occur. Patients often feel they are not taking any antipsychotic drug. It has a potent affinity for the sigma receptor, but it is unclear whether it is a sigma agonist or antagonist. The contribution of this property to its clinical profile is unknown. Blocking the D2 dopamine receptor is known to cause relapse in patients that have achieved remission from depression, and such blocking also counteracts the effectiveness of SSRI medication.
• Affected Organisms: Humans and other mammals
• Biotransformation: No active metabolites
• Absorption: Rapidly absorbed. Absolute bioavailability is 90%.
• Half Life: 4-7 hours
• Protein Binding: 89-98%
• External Links: Wikipedia