Prucalopride | CAS#179474-81-8 | 5-HT4R agonist

MedKoo Cat#: 562916 | Name: Prucalopride

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Description:

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

Prucalopride is a serotonin type 4 (5-HT4) receptor agonist that has potent prokinetic activity and is used as therapy for chronic idiopathic constipation. Prucalopride has applications in treating diabetic and idiopathic gastroparesis.

Chemical Structure

Prucalopride

CAS#179474-81-8 (free base)

Theoretical Analysis

MedKoo Cat#: 562916

Name: Prucalopride

CAS#: 179474-81-8 (free base)

Chemical Formula: C18H26ClN3O3

Exact Mass: 367.1663

Molecular Weight: 367.87

Elemental Analysis: C, 58.77; H, 7.12; Cl, 9.64; N, 11.42; O, 13.05

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
250mg	USD 1,450.00	2 Weeks

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Related CAS #

179474-85-2 (Succinate) 179474-81-8 (free base) 179474-80-7 (HCl)

Synonym

R-108512; R 108512; R108512; R 093877; R-093877; R093877; R 93877; R-93877; R93877； Prucalopride; Prucalopride free base; Motegrity; Resolor; Resotran;

IUPAC/Chemical Name

4-amino-5-chloro-N-(1-(3-methoxypropyl)piperidin-4-yl)-2,3-dihydrobenzofuran-7-carboxamide

InChi Key

ZPMNHBXQOOVQJL-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H26ClN3O3/c1-24-9-2-6-22-7-3-12(4-8-22)21-18(23)14-11-15(19)16(20)13-5-10-25-17(13)14/h11-12H,2-10,20H2,1H3,(H,21,23)

SMILES Code

ClC1=CC(C(NC2CCN(CCCOC)CC2)=O)=C3C(CCO3)=C1N

Appearance

Solid powder

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 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:

Prucalopride is a 5-HT 4 receptor agonist with pKis of 8.6 and 8.1 for human 5-HT4a/4b receptors, respectively.

In vitro activity:

Prucalopride exhibited inhibitory effects on cell proliferation, invasion, and migration in A549 and A427 lung cancer cells. Prucalopride induced autophagy and apoptosis while downregulating the phosphorylation of protein kinase B (AKT) and mammalian target of rapamycin in the PI3K/AKT/mTor signaling pathway. Reference: Hum Exp Toxicol. 2020 Feb;39(2):173-181. https://pubmed.ncbi.nlm.nih.gov/31640407/

In vivo activity:

Prucalopride was administered to diabetic rats, and its effects on intestinal motility and the regeneration of the enteric nervous system (ENS) were examined. The diabetic rats exhibited prolonged colonic transit time, which was significantly shortened by prucalopride treatment. In prucalopride-treated groups, there was increased expression of Nestin, GFAP, SOX10, RNA- HuD, and PGP9.5. Prucalopride also led to increased 5-HT levels. These findings suggest that prucalopride improves intestinal motility by promoting ENS regeneration in rats with DM. Reference: Int J Mol Med. 2022 Jul;50(1):87. https://pubmed.ncbi.nlm.nih.gov/35543167/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	54.37
	DMSO	10.0	27.18
	Ethanol	10.0	27.18

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 367.87 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. Chen M, Zhu LL, Su JL, Li GL, Wang J, Zhang YN. Prucalopride inhibits lung cancer cell proliferation, invasion, and migration through blocking of the PI3K/AKT/mTor signaling pathway. Hum Exp Toxicol. 2020 Feb;39(2):173-181. doi: 10.1177/0960327119883409. Epub 2019 Oct 22. PMID: 31640407. 2. Bianco F, Bonora E, Natarajan D, Vargiolu M, Thapar N, Torresan F, Giancola F, Boschetti E, Volta U, Bazzoli F, Mazzoni M, Seri M, Clavenzani P, Stanghellini V, Sternini C, De Giorgio R. Prucalopride exerts neuroprotection in human enteric neurons. Am J Physiol Gastrointest Liver Physiol. 2016 May 15;310(10):G768-75. doi: 10.1152/ajpgi.00036.2016. Epub 2016 Feb 18. PMID: 26893157; PMCID: PMC5243219. 3. Wang Y, Xu X, Lin L. Prucalopride might improve intestinal motility by promoting the regeneration of the enteric nervous system in diabetic rats. Int J Mol Med. 2022 Jul;50(1):87. doi: 10.3892/ijmm.2022.5143. Epub 2022 May 11. PMID: 35543167; PMCID: PMC9162040. 4. Shi Y, Qiao CM, Zhou Y, Wu J, Cui C, Hong H, Jia XB, Huang SB, Yao L, Zhao WJ, Shen YQ. Protective effects of prucalopride in MPTP-induced Parkinson's disease mice: Neurochemistry, motor function and gut barrier. Biochem Biophys Res Commun. 2021 Jun 4;556:16-22. doi: 10.1016/j.bbrc.2021.03.109. Epub 2021 Apr 6. PMID: 33836343.

In vitro protocol:

In vivo protocol:

1. Wang Y, Xu X, Lin L. Prucalopride might improve intestinal motility by promoting the regeneration of the enteric nervous system in diabetic rats. Int J Mol Med. 2022 Jul;50(1):87. doi: 10.3892/ijmm.2022.5143. Epub 2022 May 11. PMID: 35543167; PMCID: PMC9162040. 2. Shi Y, Qiao CM, Zhou Y, Wu J, Cui C, Hong H, Jia XB, Huang SB, Yao L, Zhao WJ, Shen YQ. Protective effects of prucalopride in MPTP-induced Parkinson's disease mice: Neurochemistry, motor function and gut barrier. Biochem Biophys Res Commun. 2021 Jun 4;556:16-22. doi: 10.1016/j.bbrc.2021.03.109. Epub 2021 Apr 6. PMID: 33836343.

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Expert Rev Gastroenterol Hepatol. 2024 Jul 15:1-7. doi: 10.1080/17474124.2024.2380315. Epub ahead of print. PMID: 38995209. 4: Gordon M, Grafton-Clarke C, Rajindrajith S, Benninga MA, Sinopoulou V, Akobeng AK. Treatments for intractable constipation in childhood. Cochrane Database Syst Rev. 2024 Jun 19;6(6):CD014580. doi: 10.1002/14651858.CD014580.pub2. PMID: 38895907; PMCID: PMC11190639. 5: Abu-Hassan AA, Mahdi WA, Alshehri S, El Hamd MA. An ingenious technique based on the usage of fluorone-based dye; pyrosin B in prucalopride assay in different matrices through an "on-off" dye native fluorescence probe. Luminescence. 2024 May;39(5):e4752. doi: 10.1002/bio.4752. PMID: 38697778. 6: Jiang S, Sydney EJ, Runyan AM, Serpe R, Srikanth M, Figueroa HY, Yang M, Myeku N. 5-HT4 receptor agonists treatment reduces tau pathology and behavioral deficit in the PS19 mouse model of tauopathy. Front Cell Neurosci. 2024 Apr 4;18:1338502. doi: 10.3389/fncel.2024.1338502. PMID: 38638303; PMCID: PMC11024353. 7: Talwar G, Sharma S, McKechnie T, Yang S, Khamar J, Hong D, Doumouras A, Eskicioglu C. Prucalopride and Bowel Function Post Gastrointestinal Surgery: Systematic Review and Meta-Analysis of Randomized Controlled Trials. Am Surg. 2024 Jun;90(6):1682-1701. doi: 10.1177/00031348241241683. Epub 2024 Mar 26. PMID: 38530772. 8: Badr El-Din KM, Derayea SM, Mohammed FF, Hamad AA. Integrated resonance Rayleigh scattering approach utilizing Box-Behnken experimental design for the facile quantification of prucalopride in pharmaceutical tablets and human urine with sustainability assessment. RSC Adv. 2024 Mar 5;14(11):7797-7805. doi: 10.1039/d3ra07980e. PMID: 38444975; PMCID: PMC10913158. 9: Raouf Z, Steinway SN, Scheese D, Lopez CM, Duess JW, Tsuboi K, Sampah M, Klerk D, El Baassiri M, Moore H, Tragesser C, Prindle T Jr, Wang S, Wang M, Jang HS, Fulton WB, Sodhi CP, Hackam DJ. Colitis-Induced Small Intestinal Hypomotility Is Dependent on Enteroendocrine Cell Loss in Mice. Cell Mol Gastroenterol Hepatol. 2024;18(1):53-70. doi: 10.1016/j.jcmgh.2024.02.017. Epub 2024 Mar 2. PMID: 38438014; PMCID: PMC11127033. 10: Abernethy EK, Aly EH. Postoperative Ileus after Minimally Invasive Colorectal Surgery: A Summary of Current Strategies for Prevention and Management. Dig Surg. 2024;41(2):79-91. doi: 10.1159/000537805. Epub 2024 Feb 15. PMID: 38359801; PMCID: PMC11025667. 11: Lembo A, Cash BD, Lu M, Terasawa E, Terreri B, Du S, Ayyagari R, Feuerstadt P, Moshiree B, Westermeyer B, Pi S, Boules M. Clinical Outcomes Before and After Prucalopride Treatment: An Observational Study in Patients With Chronic Idiopathic Constipation in the United States. Clin Transl Gastroenterol. 2024 May 1;15(5):e00687. doi: 10.14309/ctg.0000000000000687. PMID: 38357940; PMCID: PMC11124638. 12: Patel P, Zaher EA, Khataniar H, Ebrahim MA, Loganathan P. Safety and Efficacy of Highly Selective 5-Hydroxytryptamine Receptor 4 Agonists for Diabetic and Idiopathic Gastroparesis: A Systematic Review and Meta-Analysis of Randomized Controlled Trials. Cureus. 2024 Jan 8;16(1):e51851. doi: 10.7759/cureus.51851. PMID: 38327939; PMCID: PMC10848606. 13: Velez A, Kaul A, El-Chammas KI, Knowlton L, Madis E, Sahay R, Fei L, Stiehl S, Santucci NR. Safety and Effectiveness of Prucalopride in Children with Functional Constipation with and without Upper Symptoms. Paediatr Drugs. 2024 Mar;26(2):187-195. doi: 10.1007/s40272-023-00612-8. Epub 2024 Jan 4. PMID: 38175354; PMCID: PMC11114085. 14: Soares GA, Rodrigues GS, Buranello LP, de Oliveira RB, de Arruda Miranda JR. Pharmacomagnetography assessment of the prokinetic effect on metronidazole absorption. J Pharm Pharmacol. 2023 Dec 8;75(12):1560-1568. doi: 10.1093/jpp/rgad088. PMID: 37831664. 15: Okdahl T, Emmanuel A, Morlion B, Farmer A, Varrassi G, Drewes AM. Recommendations for the management of opioid-induced constipation - how to improve usability in clinical practice. Expert Rev Gastroenterol Hepatol. 2023 Jul-Dec;17(10):975-983. doi: 10.1080/17474124.2023.2267441. Epub 2023 Oct 24. PMID: 37822210. 16: Cha RR, Park SY, Camilleri M; Constipation Research Group of Korean Society of Neurogastroenterology and Motility. Constipation in Patients With Chronic Kidney Disease. J Neurogastroenterol Motil. 2023 Oct 30;29(4):428-435. doi: 10.5056/jnm23133. PMID: 37814433; PMCID: PMC10577456. 17: Chen BK, Luna VM, Jin M, Shah A, Shannon ME, Pauers M, Williams BL, Pham V, Hunsberger HC, Gardier AM, Mendez-David I, David DJ, Denny CA. A tale of two receptors: simultaneous targeting of NMDARs and 5-HT 4 Rs exerts additive effects against stress. bioRxiv [Preprint]. 2023 Sep 27:2023.09.27.559065. doi: 10.1101/2023.09.27.559065. PMID: 37808799; PMCID: PMC10557654. 18: Derayea SM, Mohammed FF, Badr El-Din KM. Sensitive spectrofluorimetric determination of the prokinetic drug prucalopride succinate based on supramolecular aggregation approach with evaluation of method greenness: application to content uniformity test. Luminescence. 2023 Dec;38(12):2065-2072. doi: 10.1002/bio.4597. Epub 2023 Oct 10. PMID: 37740522. 19: Sen A, Chokshi R. Update on the Diagnosis and Management of Acute Colonic Pseudo-obstruction (ACPO). Curr Gastroenterol Rep. 2023 Sep;25(9):191-197. doi: 10.1007/s11894-023-00881-w. Epub 2023 Jul 24. PMID: 37486594. 20: Salman BI. Green microwave quantum dots as luminescent probes for quantifying prucalopride: consistency of content and application to pharmacokinetic studies. BMC Chem. 2023 Jul 19;17(1):83. doi: 10.1186/s13065-023-01002-4. PMID: 37468925; PMCID: PMC10357765.