Prucalopride
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MedKoo CAT#: 562916

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

Description: Prucalopride is a 5-HT4R agonist.


Chemical Structure

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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: 367.17
Molecular Weight: 367.870
Elemental Analysis: C, 58.77; H, 7.12; Cl, 9.64; N, 11.42; O, 13.05

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
250mg USD 1450 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:
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/

Solubility Data

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

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.

Recalculate based on batch purity %
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: 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.
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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1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548650/ PubMed PMID: 31643961.

2: Tameez Ud Din A, Khan AH, Bajwa H, Maqsood MH, Malik MN. Clinical Efficacy and Safety Profile of Prucalopride in Chronic Idiopathic Constipation. Cureus. 2019 Apr 4;11(4):e4382. doi: 10.7759/cureus.4382. Review. PubMed PMID: 31218146; PubMed Central PMCID: PMC6553670.

3: Vijayvargiya P, Camilleri M. Use of prucalopride in adults with chronic idiopathic constipation. Expert Rev Clin Pharmacol. 2019 Jul;12(7):579-589. doi: 10.1080/17512433.2019.1620104. Epub 2019 May 23. Review. PubMed PMID: 31096799.

4: Bassotti G, Usai Satta P, Bellini M. Prucalopride for the treatment of constipation: a view from 2015 and beyond. Expert Rev Gastroenterol Hepatol. 2019 Mar;13(3):257-262. doi: 10.1080/17474124.2019.1568238. Epub 2019 Jan 23. Review. PubMed PMID: 30791758.

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6: Ho C, Severn M. Prucalopride for Gastrointestinal Motility Disorders: A Review of Clinical Effectiveness [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2017 Dec 6. Available from http://www.ncbi.nlm.nih.gov/books/NBK526294/ PubMed PMID: 30260606.

7: Omer A, Quigley EMM. An update on prucalopride in the treatment of chronic constipation. Therap Adv Gastroenterol. 2017 Nov;10(11):877-887. doi: 10.1177/1756283X17734809. Epub 2017 Oct 16. Review. PubMed PMID: 29147138; PubMed Central PMCID: PMC5673021.

8: Smart CJ, Malik KI. Prucalopride for the treatment of ileus. Expert Opin Investig Drugs. 2017 Apr;26(4):489-493. doi: 10.1080/13543784.2017.1301427. Epub 2017 Mar 10. Review. PubMed PMID: 28277883.

9: Shin A. Patient considerations in the management of chronic constipation: focus on prucalopride. Patient Prefer Adherence. 2016 Jul 28;10:1373-84. doi: 10.2147/PPA.S92550. eCollection 2016. Review. PubMed PMID: 27528801; PubMed Central PMCID: PMC4970632.

10: Bellini M, Gambaccini D, Bassotti G. Prucalopride: For functional constipation only? Tech Coloproctol. 2016 Jul;20(7):433-6. doi: 10.1007/s10151-016-1477-8. Epub 2016 May 12. Review. PubMed PMID: 27174045.

11: Bassotti G, Gambaccini D, Bellini M. Prucalopride succinate for the treatment of constipation: an update. Expert Rev Gastroenterol Hepatol. 2016;10(3):291-300. doi: 10.1586/17474124.2016.1129897. Epub 2016 Jan 29. Review. PubMed PMID: 26647167.

12: Garnock-Jones KP. Prucalopride: A Review in Chronic Idiopathic Constipation. Drugs. 2016 Jan;76(1):99-110. doi: 10.1007/s40265-015-0518-3. Review. PubMed PMID: 26628294.

13: Diederen K, Mugie SM, Benninga MA. Efficacy and safety of prucalopride in adults and children with chronic constipation. Expert Opin Pharmacother. 2015 Feb;16(3):407-16. doi: 10.1517/14656566.2015.996547. Epub 2014 Dec 24. Review. PubMed PMID: 25539475.

14: Retraction: "Chronic constipation-associated symptoms in Asians and non-Asians, and effects of 12-week prucalopride treatment: A pooled analysis of 4 randomized, placebo-controlled trials" by Suck Chei CHOI, Duo Wu ZOU, Mei Yun KE, Somchai LEELAKUSOLVONG, Jan TACK, Eamonn MM QUIGLEY, Andy LIU and Jin Yong KIM. J Dig Dis. 2016 Apr;17(4):277. doi: 10.1111/1751-2980.12219. Review. PubMed PMID: 25495559.

15: Bellacosa L, Cogliandro R, Cremon C, De Giorgio R, Barbara G, Stanghellini V. [Some practical questions on chronic stipsis treatment with prucalopride]. Minerva Gastroenterol Dietol. 2014 Mar;60(1):85-99. Review. Italian. PubMed PMID: 24632771.

16: Shin A, Camilleri M, Kolar G, Erwin P, West CP, Murad MH. Systematic review with meta-analysis: highly selective 5-HT4 agonists (prucalopride, velusetrag or naronapride) in chronic constipation. Aliment Pharmacol Ther. 2014 Feb;39(3):239-53. doi: 10.1111/apt.12571. Epub 2013 Dec 5. Review. PubMed PMID: 24308797.

17: Keating GM. Prucalopride: a review of its use in the management of chronic constipation. Drugs. 2013 Nov;73(17):1935-50. doi: 10.1007/s40265-013-0140-1. Review. PubMed PMID: 24194435.

18: Tack J, Corsetti M. Prucalopride: evaluation of the pharmacokinetics, pharmacodynamics, efficacy and safety in the treatment of chronic constipation. Expert Opin Drug Metab Toxicol. 2012 Oct;8(10):1327-35. doi: 10.1517/17425255.2012.719497. Review. PubMed PMID: 22985444.

19: Pennant M, Orlando R, Barton P, Bayliss S, Routh K, Meads C. Prucalopride for the treatment of women with chronic constipation in whom standard laxative regimens have failed to provide adequate relief. Health Technol Assess. 2011 May;15 Suppl 1:43-50. doi: 10.3310/hta15suppl1/05. Review. PubMed PMID: 21609652.

20: What role for prucalopride in constipation? Drug Ther Bull. 2011 Aug;49(8):93-6. doi: 10.1136/dtb.2011.02.0050. Review. PubMed PMID: 21831905.