Details of the Drug

General Information of Drug (ID: DMGQF3R)

Drug Name
Remoxipride
Synonyms
Remoxiprida; Remoxipridum; Romoxipride; A 33547; FLA 731; A-33547; FLA-731; Remoxiprida [INN-Spanish]; Remoxipride (USAN); Remoxipridum [INN-Latin]; Remoxipride [USAN:BAN:INN]; (-)-(S)-3-Brom-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dimethoxybenzamid; (-)-(S)-3-Bromo-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dimethoxybenzamide; (-)-n-ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine; (S)-3-Bromo-2,6-dimethoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide; (S)-3-Bromo-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dimethoxybenzamide; 3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxybenzamide
Indication
Disease Entry ICD 11 Status REF
Schizophrenia 6A20 Withdrawn from market [1]
Therapeutic Class
Antipsychotic Agents
Affected Organisms
Humans and other mammals
ATC Code
N05AL04: Remoxipride
N05AL: Benzamides
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AL04: Remoxipride
N05AL: Benzamides
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 371.27
Logarithm of the Partition Coefficient (xlogp) 2.1
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 39 +/- 9 micromolh/L [2]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 5.5 +/- 1.1 micromol/L [2]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 0.8 +/- 0.2 h [2]
Bioavailability
The bioavailability of drug is 90% [2]
Clearance
The renal clearance of drug is 23.6 +/- 7.0 mL/min [2]
Elimination
89% of drug is recovered in the urine and 7% of drug is recovered in the feces [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 5.1 +/- 1.6 hours (in patients with normal creatinine clearance), 6.1 +/- 2.6 hours (in patients with moderate renal impairment), and 9.9 +/- 3.8 hours (in patients with severe renal impairment) [2]
Unbound Fraction
The unbound fraction of drug in plasma is 0.16% [4]
Vd
The volume of distribution (Vd) of drug is 44.3 +/- 8.3 L [2]
Chemical Identifiers
Formula
C16H23BrN2O3
IUPAC Name
3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxybenzamide
Canonical SMILES
CCN1CCC[C@H]1CNC(=O)C2=C(C=CC(=C2OC)Br)OC
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
Cross-matching ID
PubChem CID
54477
ChEBI ID
CHEMBL22242
CAS Number
80125-14-0
UNII
0223RD59PE
DrugBank ID
DB00409
TTD ID
D01PIL
INTEDE ID
DR1403
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Antagonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Schizophrenia
ICD Disease Classification 6A20
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine D2 receptor (D2R) DTT DRD2 2.50E-02 -0.08 -0.49
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.30E-01 -1.91E-02 -1.41E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Pharmacology of the atypical antipsychotic remoxipride, a dopamine D2 receptor antagonist. CNS Drug Rev. 2001 Fall;7(3):265-82.
2 The pharmacokinetics of remoxipride and metabolites in patients with various degrees of renal function. Br J Clin Pharmacol. 1993 Jun;35(6):615-22. doi: 10.1111/j.1365-2125.1993.tb04191.x.
3 von Bahr C, Movin G, Yisak WA, Jostell KG, Widman M: Clinical pharmacokinetics of remoxipride. Acta Psychiatr Scand Suppl. 1990;358:41-4. doi: 10.1111/j.1600-0447.1990.tb05284.x.
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38.
6 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.