Synonym
Remoxipride Hydrochloride (anhydrous); Remoxipride HCl; Roxiam; A 33547 hydrochloride; UNII-QS4S72U30K; QS4S72U30K; Remoxipride Hydrochloride Anhydrous ; Remoxipride Monohydrochloride; Remoxipride Monohydrochloride Monohydrate; Remoxipride Monohydrochloride, (R)-Isomer; Remoxipride, (R)-Isomer;
IUPAC/Chemical Name
3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxybenzamide;hydrochloride
InChi Key
WCPXLMIPGMFZMY-MERQFXBCSA-N
InChi Code
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
SMILES Code
CCN1CCCC1CNC(=O)C2=C(C=CC(=C2OC)Br)OC.Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in water
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Remoxipride is a dopamine D2 receptor antagonist (Ki = 0.2 µM). It shows selectivity over D3 and D4 receptors (Ki values are ~ 300, ~ 1600, and ~ 2800 nM for D2, D3 and D4 receptors respectively). Formulations containing remoxipride have previously been used in schizophrenia treatment.
In vitro activity:
These results demonstrate that the remoxipride metabolite NCQ-344 is capable of facile formation of a reactive para-quinone capable of reacting with glutathione. This may rationalize previous findings regarding the biological effects observed in vitro with NCQ-344 and NCQ-436, two remoxipride metabolites.
Reference: Chem Res Toxicol. 2004 Apr;17(4):564-71. https://pubmed.ncbi.nlm.nih.gov/15089099/
In vivo activity:
The clinical efficacy of remoxipride is similar to that of haloperidol or chlorpromazine. Remoxipride has been found to exhibit relatively high selectivity for dopamine D2 receptors making it an interesting tool for neurochemical and behavioral studies.
Reference: CNS Drug Rev. 2001 Fall;7(3):265-82. https://pubmed.ncbi.nlm.nih.gov/11607043/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
40.8 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
407.73
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Erve JC, Svensson MA, von Euler-Chelpin H, Klasson-Wehler E. Characterization of glutathione conjugates of the remoxipride hydroquinone metabolite NCQ-344 formed in vitro and detection following oxidation by human neutrophils. Chem Res Toxicol. 2004 Apr;17(4):564-71. doi: 10.1021/tx034238n. PMID: 15089099.
2. Inayat-Hussain SH, McGuinness SM, Johansson R, Lundstrom J, Ross D. Caspase-dependent and -independent mechanisms in apoptosis induced by hydroquinone and catechol metabolites of remoxipride in HL-60 cells. Chem Biol Interact. 2000 Aug 15;128(1):51-63. doi: 10.1016/s0009-2797(00)00188-5. PMID: 10996300.
3. Nadal R. Pharmacology of the atypical antipsychotic remoxipride, a dopamine D2 receptor antagonist. CNS Drug Rev. 2001 Fall;7(3):265-82. doi: 10.1111/j.1527-3458.2001.tb00199.x. PMID: 11607043; PMCID: PMC6741677.
4. Trimble KM, Bell R, King DJ. Enhancement of latent inhibition in the rat by the atypical antipsychotic agent remoxipride. Pharmacol Biochem Behav. 1997 Apr;56(4):809-16. doi: 10.1016/s0091-3057(96)00483-2. PMID: 9130309.
In vitro protocol:
1. Erve JC, Svensson MA, von Euler-Chelpin H, Klasson-Wehler E. Characterization of glutathione conjugates of the remoxipride hydroquinone metabolite NCQ-344 formed in vitro and detection following oxidation by human neutrophils. Chem Res Toxicol. 2004 Apr;17(4):564-71. doi: 10.1021/tx034238n. PMID: 15089099.
2. Inayat-Hussain SH, McGuinness SM, Johansson R, Lundstrom J, Ross D. Caspase-dependent and -independent mechanisms in apoptosis induced by hydroquinone and catechol metabolites of remoxipride in HL-60 cells. Chem Biol Interact. 2000 Aug 15;128(1):51-63. doi: 10.1016/s0009-2797(00)00188-5. PMID: 10996300.
In vivo protocol:
1. Nadal R. Pharmacology of the atypical antipsychotic remoxipride, a dopamine D2 receptor antagonist. CNS Drug Rev. 2001 Fall;7(3):265-82. doi: 10.1111/j.1527-3458.2001.tb00199.x. PMID: 11607043; PMCID: PMC6741677.
2. Trimble KM, Bell R, King DJ. Enhancement of latent inhibition in the rat by the atypical antipsychotic agent remoxipride. Pharmacol Biochem Behav. 1997 Apr;56(4):809-16. doi: 10.1016/s0091-3057(96)00483-2. PMID: 9130309.
1: Charbit AR, Akerman S, Goadsby PJ. Comparison of the effects of central and peripheral dopamine receptor activation on evoked firing in the trigeminocervical complex. J Pharmacol Exp Ther. 2009 Nov;331(2):752-63. doi: 10.1124/jpet.109.151951. Epub 2009 Aug 5. PMID: 19657051.
2: Ringqvist A, Taylor LS, Ekelund K, Ragnarsson G, Engström S, Axelsson A. Atomic force microscopy analysis and confocal Raman microimaging of coated pellets. Int J Pharm. 2003 Nov 28;267(1-2):35-47. doi: 10.1016/j.ijpharm.2003.07.004. PMID: 14602382.
3: Behan WM, Madigan M, Clark BJ, Goldberg J, McLellan DR. Muscle changes in the neuroleptic malignant syndrome. J Clin Pathol. 2000 Mar;53(3):223-7. doi: 10.1136/jcp.53.3.223. PMID: 10823143; PMCID: PMC1731156.
4: Movin-Osswald G, Boelaert J, Hammarlund-Udenaes M, Nilsson LB. 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. PMID: 8329289; PMCID: PMC1381605.
5: Ericson H, Ross SB. Subchronic treatment of rats with remoxipride fails to modify sigma binding sites in the brain. Eur J Pharmacol. 1992 Jun 5;226(2):157-61. doi: 10.1016/0922-4106(92)90177-w. PMID: 1353452.
6: Högberg T, Rämsby S, de Paulis T, Stensland B, Csöregh I, Wägner A. Solid state conformations and antidopaminergic effects of remoxipride hydrochloride and a closely related salicylamide, FLA 797, in relation to dopamine receptor models. Mol Pharmacol. 1986 Oct;30(4):345-51. PMID: 2945089.
