Loperamide hydrochloride
(Synonyms: 盐酸洛哌丁胺; R-18553 hydrochloride) 目录号 : GC36479
An Analytical Reference Standard
Cas No.:34552-83-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Loperamide is an opiate which potently and selectively activates μ opioid receptors (Ki = 0.16 nM) exclusively in the periphery. Loperamide is an opiate which potently and selectively activates μ opioid receptors (Ki = 0.16 nM) exclusively in the periphery.1,2 It is a much weaker agonist of the δ opioid receptor (Ki = 50 nM).1 Through its actions in the gut wall, loperamide has antidiarrheal action by increasing transit time and by altering intestinal transport of water and electrolytes.2,3 It also blocks voltage-
1.Breslin, H.J., Miskowski, T.A., Rafferty, B.M., et al.Rationale, design, and synthesis of novel phenyl imidazoles as opioid receptor agonists for gastrointestinal disordersJ. Med. Chem.47(21)5009-5020(2004) 2.Regnard, C., Twycross, R., Mihalyo, M., et al.LoperamideJ. Pain Symptom Manage.42(2)319-323(2011) 3.Trinkley, K.E., and Nahata, M.C.Treatment of irritable bowel syndromeJ. Clin. Pharm. Ther.36(3)275-282(2011) 4.McNeal, E.T., Lewandowski, G.A., Daly, J.W., et al.[3H]Batrachotoxinin A 20α-benzoate binding to voltage-sensitive sodium channels: A rapid and quantitative assay for local anesthetic activity in a variety of drugsJ. Med. Chem.28(3)381-388(1985) 5.Church, J., Fletcher, E.J., Abdel-Hamid, K., et al.Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neuronsMol. Pharmacol.45747-757(1994) 6.Shannon, H.E., and Lutz, E.A.Comparison of the peripheral and central effects of the opioid agonists loperamide and morphine in the formalin test in ratsNeuropharmacology42(2)253-261(2002)
| Cas No. | 34552-83-5 | SDF | |
| 别名 | 盐酸洛哌丁胺; R-18553 hydrochloride | ||
| Canonical SMILES | O=C(N(C)C)C(C1=CC=CC=C1)(C2=CC=CC=C2)CCN3CCC(O)(C4=CC=C(Cl)C=C4)CC3.Cl | ||
| 分子式 | C29H34Cl2N2O2 | 分子量 | 513.5 |
| 溶解度 | DMSO: 50 mg/mL (97.37 mM); Water: 1 mg/mL (1.95 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.9474 mL | 9.7371 mL | 19.4742 mL |
| 5 mM | 0.3895 mL | 1.9474 mL | 3.8948 mL |
| 10 mM | 0.1947 mL | 0.9737 mL | 1.9474 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Antidiarrhetic Loperamide hydrochloride
Acta Crystallogr C 2012 Mar;68(Pt 3):o111-3.PMID:22382543DOI:10.1107/S010827011200443X.
Single crystals of the anhydrous form of the title compound {systematic name: 1-[3-(dimethylcarbamoyl)-3,3-diphenylpropyl]-4-hydroxy-4-(4-chlorophenyl)piperidin-1-ium chloride}, C(29)H(34)ClN(2)O(2)(+)·Cl(-), were obtained by diffusion of acetone into a solution in 2-propanol. In the structure, N-H...Cl(-) and O-H...Cl(-) hydrogen bonds connect neighbouring molecules and chloride anions to form chains along the c-axis direction. Neighbouring chains along the b-axis direction are connected by intermolecular C-H...Cl(-) contacts, defining layers parallel to the (100) planes. The layers are connected by weak intermolecular C-H...Cl interactions only, which may account for the plate-like shape of the crystals.
Improvement of loperamide-hydrochloride-induced intestinal motility disturbance by Platycodon grandiflorum polysaccharides through effects on gut microbes and colonic serotonin
Front Cell Infect Microbiol 2023 Mar 13;13:1105272.PMID:36992686DOI:10.3389/fcimb.2023.1105272.
Constipation is a common gastrointestinal symptom characterized by intestinal motility disorder. The effects of Platycodon grandiflorum polysaccharides (PGP) on intestinal motility have not been confirmed. We established a rat model of constipation induced by Loperamide hydrochloride to elucidate the therapeutic effect of PGP on intestinal motility disorder and to explore the possible mechanism. After PGP treatment (400 and 800 mg/kg) for 21 d, PGP clearly relieved gastrointestinal motility, including fecal water content, gastric emptying rate, and intestinal transit rate. Moreover, the secretion of motility-related hormones, gastrin and motilin, were increased. Enzyme-linked immunosorbent assay, western blot, immunohistochemistry, and immunofluorescence results confirmed that PGP significantly increased the secretion of 5-hydroxytryptamine (5-HT) and the expression of related proteins, such as tryptophan hydroxylase 1, 5-HT4 receptor, and transient receptor potential ankyrin 1. 16S rRNA gene sequencing showed that PGP significantly increased the relative abundance of Roseburia, Butyricimonas, and Ruminiclostridium, which were positively correlated with 5-HT levels. However, the relative abundance of Clostridia_UCG-014, Lactobacillus, and Enterococcus were decreased. PGP improved intestinal transport by regulating the levels of 5-HT, which interacts with the gut microbiota and the intestinal neuro-endocrine system, further affecting constipation. Overall, PGP is a potential supplement for the treatment of constipation.
Cytotoxic effects of Loperamide hydrochloride on canine cancer cells
J Vet Med Sci 2014 Dec;76(12):1563-8.PMID:25649936DOI:10.1292/jvms.13-0537.
Loperamide is a peripheral opiate agonist that can cause apoptosis and G2/M arrest in human cancer cell lines and may sensitize cells to chemotherapy. The objectives of this study were to investigate the effects of loperamide on viability, apoptosis and cell cycle kinetics in canine cancer cells and to establish whether the drug sensitizes cells to doxorubicin. Cell viability was assessed using Alamar Blue. Cell death and cell cycle were studied using flow cytometry with 7-Aminoactinomycin-D (7-AAD) and propidium iodide (PI), respectively. Loperamide decreased cell viability in a dose-dependent fashion and was most effective against canine osteosarcoma cells. In all cell lines, it induced a dose and time dependent apoptosis and resulted in accumulation in G0/G1. When co-incubated with doxorubicin, loperamide induced a synergistic cell kill in canine carcinoma cells. Investigation is warranted into the role of loperamide in the treatment of canine cancer.
LC-MS determination and bioavailability study of Loperamide hydrochloride after oral administration of loperamide capsule in human volunteers
J Pharm Biomed Anal 2004 Oct 29;36(2):421-7.PMID:15496339DOI:10.1016/j.jpba.2004.06.020.
The purpose of the present study was to develop a standard protocol for Loperamide hydrochloride bioequivalence testing. For this purpose, a simple rapid and selective LC-MS method utilizing a single quadrupole mass spectrometer was developed and validated for the determination of Loperamide hydrochloride in human plasma, and we followed this with a bioavailability study. Methyl tert-butylether (MTBE) was used to extract Loperamide hydrochloride and ketoconazole (internal standard (IS)) from an alkaline plasma sample. LC separation was performed on a Zorbax RX C18 column (5 microm, 2.1 mm x 150 mm) using acetonitrile-water-formic acid (50:50:0.1 (v/v)) as a mobile phase. The retention times of Loperamide hydrochloride and IS were 1.2 and 0.8 min, respectively. Quadrupole MS detection was by monitoring at m/z 477 (M + 1) corresponding to Loperamide hydrochloride and at m/z 531 (M + 1) for IS. The described assay method showed acceptable precision, accuracy, linearity, stability, and specificity. The bioavailability of Loperamide hydrochloride was evaluated in eight healthy male volunteers. The following pharmacokinetic parameters were elucidated after administering a single dose of four 2mg capsules of loperamide: the area under the plasma concentration versus time curve from time 0 to 72 h (AUC72 h) 19.26 +/- 7.79 ng h/ml; peak plasma concentration (Cmax) 1.18 +/- 0.37 ng/ml; time to Cmax (Tmax) 5.38 +/- 0.74 h; and elimination half-life (t1/2) 11.35 +/- 2.06 h. The developed method was successfully used to study the bioavailability of a low dose (8 mg) of Loperamide hydrochloride.
Loperamide-induced cardiotoxicity in rats: Evidence from cardiac and oxidative stress biomarkers
J Biochem Mol Toxicol 2019 Apr;33(4):e22278.PMID:30597669DOI:10.1002/jbt.22278.
At therapeutic dose, loperamide is a safe over-the-counter antidiarrheal drug but could induce cardiotoxic effect at a supratherapeutic dose. In this study, we use cardiac and oxidative biomarkers to evaluate loperamide-induced cardiotoxicity in rats. Rats were orally gavaged with 1.5, 3, or 6 mg/kg body weight (BW) of Loperamide hydrochloride for 7 days. The results after 7 days administration of loperamide, revealed dose-dependent increase (P < 0.05) in aspartate aminotransferase, lactate dehydrogenase, creatine kinase-MB, and serum concentration of cardiac troponin I, total homocysteine, and nitric oxide. A 50% decrease in antioxidant enzymes activity was observed at 6 mg/kg BW. Furthermore, malondialdehyde and fragmented DNA also increased significantly in the heart of the treatment groups. Loperamide provoked cardiotoxicity through oxidative stress, lipid peroxidation, and DNA fragmentation in rats. This study has provided a possible biochemical explanation for the reported cardiotoxicity induced by loperamide overdose.