| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
Eticlopride HCl (FLB131; FLB-131) is a potent antipsychotic agent acting as a selective dopamine D2‐like receptor antagonist. It exhibits high affinity for dopamine D2, α1‐adrenergic, α2‐adrenergic, 5HT1, 5HT2 receptors with Kis of 0.09, 112, 699, 6220, and 830 nM, respectively.
| Targets |
D2 receptor ( Ki = 0.09 nM )
Eticlopride is a high-affinity and selective antagonist for dopamine D2-like receptors. Its affinity (Ki) for the dopamine D2 receptor is 0.09 nM, as determined by displacement of ³H-spiperone binding. Its affinity for the dopamine D1 receptor is >10,000 nM (Ki). [1] Eticlopride also shows affinity for other receptors: α1-adrenergic (Ki = 11 nM), α2-adrenergic (Ki = 699 nM), 5HT1 (Ki = 6,220 nM), 5HT2 (Ki = 830 nM), histamine-H1 (Ki = 14,800 nM), muscarinic (Ki = 14,200 nM), and β-adrenergic (Ki = 95,900 nM). [1] |
|---|---|
| ln Vitro |
Eticlopride potently displaces ³H-spiperone binding from rat, pig, or calf brain striatum membranes, with an IC50 value of 0.6 nM. It has a negligible displacement of [³H]flupenthixol binding to D1 receptors (IC50 = >100,000 nM) and does not inhibit dopamine-stimulated adenylate cyclase at concentrations below 100 µM. [1]
In ex vivo autoradiography studies, [³H]Eticlopride accumulated most densely in the striatum, olfactory tubercles, and nucleus accumbens, with negligible accumulation in the cerebellum. The striatum-to-cerebellum distribution volume ratio (DVR) reached approximately 10:1. [1] Eticlopride (0.1-10 µM) was used in a study examining the inhibition of dopamine release in rat striatal slices, where it antagonized the inhibitory effect of quinpirole (a D2/D3 agonist) on [³H]dopamine release. [1] |
| ln Vivo |
In a conditioned avoidance response paradigm in rats, Eticlopride (0.01 and 0.05 mg/kg, s.c.) disrupted avoidance responding by increasing the latency to hold down a lever, with no effect on escape latency. [1]
In a study on microcatalepsy during operant performance in rats, chronic treatment (3 weeks) with Eticlopride (0.16 mg/kg, i.p.) showed no effects on Day 1 but exhibited sensitization over the 3 weeks, increasing both disruption of operant responding and induction of microcatalepsy. [1] In a conditioned reaction-time paradigm, Eticlopride (0.005 - 0.02 mg/kg, s.c.) produced dose-dependent increases in the number of incorrect responses in rats. [1] In a Pavlovian fear conditioning study in rats, intra-amygdala infusion of Eticlopride (dose not specified) before acquisition trials did not affect the acquisition of the conditioned response, but it reduced freezing behavior during retention testing, indicating that D2-like receptors in the amygdala contribute to associative learning. [1] Eticlopride (dose not specified) has been shown to robustly block the reinforcing effects of cocaine under several conditions and in different species. [1] Eticlopride was shown to decrease food intake in free-feeding rats, with no tolerance developing to this effect over a 2-week treatment period. Raclopride was equipotent to eticlopride in this effect. [1] |
| Animal Protocol |
Conditioned avoidance response: Rats were trained to hold down a lever until an auditory stimulus was presented, at which time they had 500 ms to release the lever to avoid a shock. Eticlopride was administered subcutaneously (s.c.) at doses of 0.01 and 0.05 mg/kg. [1]
Microcatalepsy study: Water-restricted rats were trained to lever-press for water reinforcement. Photobeams measured the duration of time the rats' muzzles were in the dipper well. Eticlopride was administered intraperitoneally (i.p.) at a dose of 0.16 mg/kg, once daily for 3 weeks. [1] Conditioned reaction-time paradigm: Rats were trained to hold down a lever until a visual stimulus was illuminated (conditioned stimulus), and had to release the lever within 700 ms to receive a food pellet. Eticlopride was administered subcutaneously (s.c.) at doses of 0.005, 0.01, and 0.02 mg/kg. [1] Pavlovian fear conditioning: Rats received three conditioning trials where a tone (conditioned stimulus) was followed by a footshock (unconditioned stimulus). Eticlopride was administered directly into the amygdala via infusion before acquisition trials and/or the retention test. [1] |
| ADME/Pharmacokinetics |
The pKa of the phenolic group of Eticlopride is 6.93 ± 0.01, and the pKa of the amino group is 9.67 ± 0.02, creating an isoelectric point of 8.30. At physiological pH (7.4), 74% of eticlopride species are in the zwitterionic form. [1]
Eticlopride readily crosses the blood-brain barrier, which is likely a function of strong internal hydrogen bonds that prevent it from acting as a hydrogen donor in biological lipophilic media. [1] [³H]Eticlopride has been used in ex vivo autoradiography studies to visualize D2-like receptors. [1] |
| Toxicity/Toxicokinetics |
In a study on feeding behavior, Eticlopride continued to decrease food intake over a 2-week treatment period, suggesting no tolerance developed to this effect. The review notes that a compensatory increase in D2-like receptor densities likely occurs, as seen with other antagonists. [1]
|
| References | |
| Additional Infomation |
5-Chloro-3-ethyl-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide is one of the salicylamide compounds.
Eticlopride is a substituted benzamide analog initially developed as a potential antipsychotic agent, but it is not used clinically. It is primarily used as a research tool for understanding D2-like receptor function. [1] Eticlopride was created by combining an ethyl group at the aromatic 5-position and a chlorine at the aromatic 3-position of the benzamide structure. It is 27 times more potent than remoxipride and nearly 35 times more potent than raclopride at displacing ³H-spiperone binding in vitro. [1] The chemical structure consists of two planes with a dihedral angle of 38°, and the asymmetric carbon atom has the S-configuration. The amide has a restricted rotational freedom, and side-chain conformations are stabilized through intramolecular hydrogen bonds forming pseudo-rings. The hydrogen bond-induced pseudo-ring C (involving the methoxy oxygen and amide nitrogen) is required for biological activity. [1] Eticlopride has been used in autoradiography to study dopamine D2-like receptor localization and density in various brain diseases, including schizophrenia. [1] The overall binding profile of Eticlopride (high D2 affinity, low affinity for α1, 5HT2, and other receptors) is similar to that reported for atypical antipsychotics. [1] |
| Molecular Formula |
C17H26CL2N2O3
|
|---|---|
| Molecular Weight |
377.306
|
| Exact Mass |
376.132
|
| Elemental Analysis |
C, 54.12; H, 6.95; Cl, 18.79; N, 7.42; O, 12.72
|
| CAS # |
97612-24-3
|
| Related CAS # |
97612-24-3 (HCl); 84226-12-0
|
| PubChem CID |
57267
|
| Appearance |
Solid powder
|
| Melting Point |
144 - 146 °C
|
| LogP |
3.1
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
23
|
| Complexity |
396
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C(C1C(O)=C(CC)C=C(Cl)C=1OC)(=O)NC[C@@H]1CCCN1CC.Cl
|
| InChi Key |
HFJFXXDHVWLIKX-YDALLXLXSA-N
|
| InChi Code |
InChI=1S/C17H25ClN2O3.ClH/c1-4-11-9-13(18)16(23-3)14(15(11)21)17(22)19-10-12-7-6-8-20(12)5-2;/h9,12,21H,4-8,10H2,1-3H3,(H,19,22);1H/t12-;/m0./s1
|
| Chemical Name |
5-chloro-3-ethyl-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-hydroxy-6-methoxybenzamide;hydrochloride
|
| Synonyms |
FLB 131; FLB131; Eticlopride; FLB-131
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~265.0 mM)
H2O: ~50 mg/mL (~132.5 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.63 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.63 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.63 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6503 mL | 13.2517 mL | 26.5034 mL | |
| 5 mM | 0.5301 mL | 2.6503 mL | 5.3007 mL | |
| 10 mM | 0.2650 mL | 1.3252 mL | 2.6503 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
|
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
