Mebeverine HCl | CAS# 2753-45-9 (HCl) | smooth muscle relaxant

MedKoo Cat#: 413241 | Name: Mebeverine HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mebeverine is an anticholinergic but its mechanism of action is not known; it appears to work directly on smooth muscle within the gastrointestinal tract and may have an anaesthetic effect, may affect calcium channels, and may affect muscarinic receptors. It is metabolized mostly by esterases, and almost completely. The metabolites are excreted in urine. Mebeverine exists in two enantiomeric forms. The commercially available product is a racemic mixture of them.

Chemical Structure

Mebeverine HCl

CAS#2753-45-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 413241

Name: Mebeverine HCl

CAS#: 2753-45-9 (HCl)

Chemical Formula: C25H36ClNO5

Exact Mass: 0.0000

Molecular Weight: 466.02

Elemental Analysis: C, 64.43; H, 7.79; Cl, 7.61; N, 3.01; O, 17.17

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 285.00	2 Weeks
1g	USD 650.00	2 Weeks

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Related CAS #

2753-45-9 (HCl) 3625-06-7 (free base)

Synonym

Mebeverine HCl; CSAG144; CSAG -144; CSAG 144; Mebeverine Hydrochloride;

IUPAC/Chemical Name

Benzoic acid, 3,4-dimethoxy-, 4-(ethyl(2-(4-methoxyphenyl)-1-methylethyl)amino)butyl ester, hydrochloride

InChi Key

PLGQWYOULXPJRE-UHFFFAOYSA-N

InChi Code

InChI=1S/C25H35NO5.ClH/c1-6-26(19(2)17-20-9-12-22(28-3)13-10-20)15-7-8-16-31-25(27)21-11-14-23(29-4)24(18-21)30-5;/h9-14,18-19H,6-8,15-17H2,1-5H3;1H

SMILES Code

O=C(OCCCCN(CC)C(C)CC1=CC=C(OC)C=C1)C2=CC=C(OC)C(OC)=C2.[H]Cl

Appearance

Solid powder

Purity

>95% (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 DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mebeverine HCl is a smooth muscle relaxant.

In vitro activity:

The transient hyperpolarization after mechanical stimulation was diminished after addition of mebeverine to the stimulation fluid when chloride transport was inhibited by bumetanide (BUME) but in the presence of amiloride (AMI), a sodium ion transport inhibitor, the drug did not influence the reaction. It was inferred that mebeverine was able to modulate transepithelial sodium ion transport and in this way to modify interaction between colonic wall and its contents during intestinal passage. Reference: Pharmacol Rep. 2006 Sep-Oct;58(5):765-9. https://pubmed.ncbi.nlm.nih.gov/17085870/

In vivo activity:

The aim of the present study was to characterize the effect of mebeverine on both small intestinal motor activity and electrogenic epithelial transport in the urethane anesthetized ferret. When dosed i.j., mebeverine (0.1-10 mg/kg) induced a decrease in potential difference towards lower lumen negativity, which was suggestive of a decrease in fluid secretion or enhancement of absorption. Reference: Eur J Pharmacol. 1992 Feb 11;211(2):143-7. https://pubmed.ncbi.nlm.nih.gov/1612107/

	Solvent	mg/mL	mM
Solubility
	DMSO	93.0	20.00

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 466.02 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. Tyrakowski T, Młodzik-Danielewicz N, Kurek W, Szaflarska-Popławska A, Czerwionka-Szaflarska M, Kapała A, Kopczyńska E, Hołyńska I, Kaczorowski P. Mebeverine influences sodium ion transport in the distal colon. Pharmacol Rep. 2006 Sep-Oct;58(5):765-9. PMID: 17085870. 2. Den Hertog A, Van den Akker J. Modification of alpha 1-receptor-operated channels by mebeverine in smooth muscle cells of guinea-pig taenia caeci. Eur J Pharmacol. 1987 Jun 26;138(3):367-74. doi: 10.1016/0014-2999(87)90475-4. PMID: 2442008. 3. Greenwood B, Mandel KG. Effect of mebeverine hydrochloride on jejunal motility and epithelial transport in the anesthetized ferret. Eur J Pharmacol. 1992 Feb 11;211(2):143-7. doi: 10.1016/0014-2999(92)90521-5. PMID: 1612107. 4. Den Hertog A, Van den Akker J. The action of mebeverine and metabolites on mammalian non-myelinated nerve fibres. Eur J Pharmacol. 1987 Jul 23;139(3):353-5. doi: 10.1016/0014-2999(87)90594-2. PMID: 2444442.

In vitro protocol:

In vivo protocol:

1. Greenwood B, Mandel KG. Effect of mebeverine hydrochloride on jejunal motility and epithelial transport in the anesthetized ferret. Eur J Pharmacol. 1992 Feb 11;211(2):143-7. doi: 10.1016/0014-2999(92)90521-5. PMID: 1612107. 2. Den Hertog A, Van den Akker J. The action of mebeverine and metabolites on mammalian non-myelinated nerve fibres. Eur J Pharmacol. 1987 Jul 23;139(3):353-5. doi: 10.1016/0014-2999(87)90594-2. PMID: 2444442.

1: Mostafa GAE, El-Tohamy MF, Alrabiah H. Prospective of Agro-Waste Husks for Biogenic Synthesis of Polymeric-Based CeO2/NiO Nanocomposite Sensor for Determination of Mebeverine Hydrochloride. Molecules. 2023 Feb 23;28(5):2095. doi: 10.3390/molecules28052095. PMID: 36903341; PMCID: PMC10004120. 2: Milusheva M, Gledacheva V, Stefanova I, Pencheva M, Mihaylova R, Tumbarski Y, Nedialkov P, Cherneva E, Todorova M, Nikolova S. In Silico, In Vitro, and Ex Vivo Biological Activity of Some Novel Mebeverine Precursors. Biomedicines. 2023 Feb 17;11(2):605. doi: 10.3390/biomedicines11020605. PMID: 36831141; PMCID: PMC9953468. 3: Abdel-Raoof AM, Fouad MM, Rashed NS, Hosni NYZ, Elsonbaty A, Abdel-Fattah A. Potentiometric determination of mebeverine hydrochloride antispasmodic drug based on molecular docking with different ionophores host-guest inclusion as a theoretical study. RSC Adv. 2023 Jan 4;13(2):1085-1093. doi: 10.1039/d2ra06127a. PMID: 36686904; PMCID: PMC9811649. 4: A Potential Role of Ethosuximide and Pentoxifylline in Relieving Abdominal Pain in Irritable Bowel Syndrome Patients Treated with Mebeverine: A Randomized, Double-Blind, Placebo-Controlled Trial [Retraction]. J Inflamm Res. 2022 Apr 14;15:2381-2382. doi: 10.2147/JIR.S369945. PMID: 35444453; PMCID: PMC9015672. 5: El-Haggar SM, Hegazy SK, Abd-Elsalam SM, Elkaeed EB, Al-Karmalawy AA, Bahaa MM. A Potential Role of Ethosuximide and Pentoxifylline in Relieving Abdominal Pain in Irritable Bowel Syndrome Patients Treated with Mebeverine: A Randomized, Double-Blind, Placebo-Controlled Trial. J Inflamm Res. 2022 Feb 19;15:1159-1172. doi: 10.2147/JIR.S346608. Retraction in: J Inflamm Res. 2022 Apr 14;15:2381-2382. PMID: 35221706; PMCID: PMC8867223. 6: Daniluk J, Malecka-Wojciesko E, Skrzydlo-Radomanska B, Rydzewska G. The Efficacy of Mebeverine in the Treatment of Irritable Bowel Syndrome-A Systematic Review. J Clin Med. 2022 Feb 17;11(4):1044. doi: 10.3390/jcm11041044. PMID: 35207315; PMCID: PMC8879004. 7: El-Haggar SM, Hegazy SK, Abd-Elsalam SM, Bahaa MM. Pentoxifylline, a nonselective phosphodiesterase inhibitor, in adjunctive therapy in patients with irritable bowel syndrome treated with mebeverine. Biomed Pharmacother. 2022 Jan;145:112399. doi: 10.1016/j.biopha.2021.112399. Epub 2021 Nov 12. PMID: 34775240. 8: Hashem A, Abdellutif MM, Laymon M, Abdullateef M, Abdelhamid A, Mosbah A, Abol-Enein H. Clinical efficacy of mebeverine for persistent nocturnal enuresis after orthotopic W-neobladder. BJU Int. 2022 Mar;129(3):387-393. doi: 10.1111/bju.15555. Epub 2021 Aug 3. PMID: 34289222. 9: Djebri A, Sadaoui Z, Belmedani M, Domergue L, Trari M. Removal efficiency of pharmaceutical drugs (Mebeverine hydrochloride MEB) by an activated carbon prepared from dates stems. J Environ Health Sci Eng. 2021 Apr 12;19(1):917-931. doi: 10.1007/s40201-021-00658-1. PMID: 34150282; PMCID: PMC8172815. 10: Rai RR, Nijhawan S. Comparative evaluation of efficacy and safety of drotaverine versus mebeverine in irritable bowel syndrome: A randomized double- blind controlled study. Saudi J Gastroenterol. 2021 May-Jun;27(3):136-143. doi: 10.4103/sjg.SJG_266_20. PMID: 33642357; PMCID: PMC8265406. 11: Hashem A, Abol-Enein H, Laymon M, Abdellutif MM, Ramez M, Taha MT, El- Hefnawy AS, Mosbah A. A Randomized Trial to Examine the Utility of Mebeverine on the Early Return of Continence Following Orthotopic Bladder Substitution. J Urol. 2021 May;205(5):1400-1406. doi: 10.1097/JU.0000000000001526. Epub 2020 Dec 22. PMID: 33350325. 12: Bedussi F, Acerbis E, Noseda R, Demagistri D, Zamprogno E, Ceschi A. False- positive urine screen test for MDMA in a patient exposed to mebeverine. Br J Clin Pharmacol. 2021 May;87(5):2397-2398. doi: 10.1111/bcp.14624. Epub 2020 Nov 16. PMID: 33200465. 13: Hasan AA, Samir RM, Abu-Zaid SS, Abu Lila AS. Revitalizing the local anesthetic effect of Mebeverine hydrochloride via encapsulation within ethosomal vesicular system. Colloids Surf B Biointerfaces. 2020 Oct;194:111208. doi: 10.1016/j.colsurfb.2020.111208. Epub 2020 Jun 20. PMID: 32590242. 14: Chakraborty DS, Hazra A, Sil A, Pain S. Will controlled release mebeverine be able to surpass placebo in treatment of diarrhoea predominant irritable bowel syndrome? J Family Med Prim Care. 2019 Oct 31;8(10):3173-3178. doi: 10.4103/jfmpc.jfmpc_522_19. PMID: 31742138; PMCID: PMC6857390. 15: Maev IV, Kucheravy YA, Tsukanov VV, Eremnia EY, Andreev DN, Abdulhakov SR, Akhmedov VA, Batskov SS, Vasyutin AV, V'yuchnova ES, Ivanchenko DN, Luzina EV, Krapivnaya OV, Onuchina EV, Osipenko MF, Simanenkov VI, Tonkih YL, Khomeriki NM, Shklyaev AE, Akimov AV, Sokolov KA. Effectiveness of mebeverine in patients with post-cholecystectomy gastrointestinal spasm: results of prospective observational program "odyssey". Ter Arkh. 2018 Aug 27;90(8):40-47. doi: 10.26442/terarkh201890840-47. PMID: 30701938. 16: Nezhadali A, Bonakdar GA. Multivariate optimization of mebeverine analysis using molecularly imprinted polymer electrochemical sensor based on silver nanoparticles. J Food Drug Anal. 2019 Jan;27(1):305-314. doi: 10.1016/j.jfda.2018.05.002. Epub 2018 Jun 6. PMID: 30648584; PMCID: PMC9298620. 17: Ferreira AO, Polonini H, da Silva SL, Aglio NCB, Abreu J, Fernandes BMA. Stability of Acetazolamide, Baclofen, Dipyridamole, Mebeverine Hydrochloride, Propylthiouracil, Quinidine Sulfate, and Topiramate Oral Suspensions in SyrSpend SF PH4. Int J Pharm Compd. 2017 Jul-Aug;21(4):339-346. PMID: 28719377. 18: El Nabarawi MA, Teaima MH, Abd El-Monem RA, El Nabarawy NA, Gaber DA. Formulation, release characteristics, and bioavailability study of gastroretentive floating matrix tablet and floating raft system of Mebeverine HCl. Drug Des Devel Ther. 2017 Apr 3;11:1081-1093. doi: 10.2147/DDDT.S131936. PMID: 28435220; PMCID: PMC5388234. 19: Moskaleva NE, Baranov PA, Mesonzhnik NV, Appolonova SA. HPLC-MS/MS method for the simultaneous quantification of desmethylmebeverine acid, mebeverine acid and mebeverine alcohol in human plasma along with its application to a pharmacokinetics study. J Pharm Biomed Anal. 2017 May 10;138:118-125. doi: 10.1016/j.jpba.2017.02.006. Epub 2017 Feb 6. PMID: 28192719. 20: Lotfy HM, Fayez YM, Michael AM, Nessim CK. Simultaneous determination of mebeverine hydrochloride and chlordiazepoxide in their binary mixture using novel univariate spectrophotometric methods via different manipulation pathways. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Feb 15;155:11-20. doi: 10.1016/j.saa.2015.10.033. Epub 2015 Oct 25. PMID: 26562180.