Constella™(EU)-Linzess™(USA): The last milestone in the long journey of the peptide linaclotide and its implications for the future of peptide drugs

Future Medicinal Chemistry

Volumn 5, Issue 3, 2013, Pages 291-300

  Góngora Benítez, Miriam ^a,b   Tulla Puche, Judit ^a,b   Albericio, Fernando ^a,b,c  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLECYSTOKININ A RECEPTOR; DEXLOXIGLUMIDE; DSP 6952; ELOBIXIBAT; ESCHERICHIA COLI ENTEROTOXIN; GUANYLIN; HCP 0613; LAXATIVE; LINACLOTIDE; LUBIPROSTONE; PLECANATIDE; PRUCALOPRIDE; RDX 5791; RESOTRAN; SEROTONIN 4 AGONIST; TD 8954; TEGASEROD; UNCLASSIFIED DRUG; UROGUANYLIN; VELUSETRAG; ZELMORM;

ARTICLE; CHRONIC IDIOPATHIC CONSTIPATION; DRUG ABSORPTION; DRUG APPROVAL; DRUG EXCRETION; DRUG HALF LIFE; DRUG INDICATION; DRUG INDUSTRY; DRUG MECHANISM; DRUG METABOLISM; DRUG STRUCTURE; ENTEROBACTER; GASTROINTESTINAL DISEASE; IRRITABLE BOWEL SYNDROME WITH CONSTIPATION; KLEBSIELLA; PATHOPHYSIOLOGY; PHARMACOPHORE; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PHASE 3 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; QUALITY OF LIFE; SYMPTOM; YERSINIA ENTEROCOLITICA;

AMINO ACID SEQUENCE; ANIMALS; CHRONIC DISEASE; COLON; CONSTIPATION; HUMANS; IRRITABLE BOWEL SYNDROME; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDES; RECEPTORS, GUANYLATE CYCLASE-COUPLED; RECEPTORS, PEPTIDE;

EID: 84874735423     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.13.5     Document Type: Article

References (88)

1. Albericio F, Kruger HG. Therapeutic peptides. Future Med. Chem. 4(12), 1527-1531 (2012).
2. Vlieghe P, Lisowski V, Martinez J, Khrestchatisky M. Synthetic therapeutic peptides: science and market. Drug Discov. Today 15, 40-56 (2010).
3. Drossman DA. The functional gastrointestinal disorders and the Rome III process. Gastroenterology 130(5), 1377-1390 (2006).
4. Longstreth GF, Thompson WG, Chey WD, Houghton LA, Mearin F, Spiller RC. Functional bowel disorders. Gastroenterology 130(5), 1480-1491 (2006).
5. Wong RK, Palsson O, Turner MJ et al. Inability of the Rome III criteria to distinguish functional constipation form constipation-subtype irritable bowel syndrome. Am. J. Gastroenterol. 105, 2228-2234 (2010).
6. Talley NJ. Functional gastrointestinal disorders as a public health problem. Neurogastroenterol. Motil. 20(Suppl. 1), 121-129 (2008).
7. Sun SX, Dibonaventura M, Purayidathil FW, Wagner JS, Dabbous O, Mody R. Impact of chronic constipation on health-related quality of life, work productivity, and healthcare resource use: an analysis of the National Health and Wellness Survey. Dig. Dis. Sci. 56, 2688-2695 (2011).
8. Faresjo A, Grodzinsky E, Johansson S, Wallander MA, Timpka T, Akerlind I. Population-based case-control study of work and psychosocial problems in patients with irritable bowel syndrome-women are more seriously affected than men. Am. J. Gastroenterol. 102, 371-379 (2007).
9. Lovell RM, Ford AC. Global prevalence of and risk factors for irritable bowel syndrome: a meta-analysis. Clinical Gastroenterol. Hepatol. 10(7), 712-721 (2012).
10. Suares NC, Ford AC. Prevalence of, and risk factors for, chronic idiopathic constipation in the community: systematic review and meta-analysis. Am. J. Gastroenterol. 106, 1582-1591 (2011).
11. Ford AC, Talley NJ. Irritable bowel syndrome. BMJ 345, e5836 (2012).
12. Hungin AP, Whorwell PJ, Tack J et al. The prevalence, patterns and impact of irritable bowel syndrome: an international survey of 40,000 subjects. Aliment. Pharmacol. Ther. 17(5), 643-650 (2003).
13. Ricci JF. Irritable bowel syndrome: a comparison of the economic (direct and indirect) burden in four European countries. Gut 51, A107 (2002).
14. Quigley EM, Bytzer P, Jones R, Mearin F. Irritable bowel syndrome: the burden and unmet needs in Europe. Dig. Liver Dis. 38(10), 717-723 (2006).
15. Hulisz D. The burden of illness of irritable bowel syndrome: current challenges and hope for the future. J. Manag. Care Pharm. 10(4), 299-309 (2004).
16. Camilleri M. Etiology and pathophysiology of irritable bowel syndrome and chronic constipation. Adv. Studies Med. 5(10b), S955-S964 (2005).
17. Öhman L, Simrén M. New insights into the pathogenesis and pathophysiology of irritable bowel syndrome. Digest. Liver Dis. 39, 201-215 (2007).
18. Wood JD. Neuropathopysiology of functional gastrointestinal disorders. World J. Gastroenterol. 13(9), 1313-1332 (2007).
19. Andresen V, Camilleri M. Irritable bowel syndrome recent and novel therapeutic approaches. Drugs 66(8), 1073-1088 (2006).
20. Menees S, Saad R, Chey WD. Agents that act luminally to treat diarrhea and constipation. Nat. Rev. Gastroenterol. Hepatol. 9, 661-674 (2012).
21. Camilleri M. Pharmacology of the new treatments for lower gastrointestinal motility disorders and irritable bowel syndrome. Clinical Pharmacol. Ther. 91(1), 44-59 (2012).
22. Evans BW, Clark WK, Moore DJ, Whorwell PJ. Tegaserod for the treatment of irritable bowel syndrome and chronic constipation. Cochrane Database Syst. Rev. 17(4), CD003960 (2007).
23. Tack J, Camilleri M, Chang L et al. Systematic review: cardiovascular safety profile of 5-HT4 agonists developed for gastrointestinal disorders. Aliment. Pharmacol. Ther. 35, 745-767 (2012).
24. Quigley EMM. Prucalopride: safety, efficacy and potential applications. Therap. Adv. Gastroenterol. 5(1), 23-30 (2012).
25. Tack J, Corsetti M. Prucalopride: evaluation of the pharmacokinetics, pharmacodynamics, efficacy and safety in the treatment of chronic constipation. Expert Opin. Drug Metab. Toxicol. 8(10), 1327-1335 (2012).
26. Goldberg M, Li YP, Johanson JF et al. Clinical trial: the efficacy and tolerability of velusetrag, a selective 5-HT4 agonist with high intrinsic activity, in chronic idiopathic constipation - a 4-week, randomized, double-blind, placebo-controlled, dose-response study. Aliment. Pharmacol. Ther. 32(9), 1102-1112 (2010).
27. Long DD, Armstrong SR, Beattie DT et al. Discovery, oral pharmacokinetics and in vivo efficacy of velusetrag, a highly selective 5-HT(4) receptor agonist that has achieved proof-of-concept in patients with chronic idiopathic constipation. Bioorg. Med. Chem. Lett. 22(19), 6048-6052 (2012).
28. Beattie DT, Armstrong SR, Vickery RG. The pharmacology of TD-8954, a potent and selective 5-HT4 receptor agonist with gastrointestinal prokinetic properties. Front. Pharmacol. 2, 25 (2011).
29. Schey R, Rao SS. Lubiprostone for the treatment of adults with constipation and irritable bowel syndrome. Dig. Dis. Sci. 56(6), 1619-1625 (2011).
30. Chamberlain SM, Rao SS. Safety evaluation of lubiprostone in the treatment of constipation and irritable bowel syndrome. Expert Opin. Drug Saf. 11(5), 841-850 (2012).
31. Cremonini F, Camilleri M, McKinzie S et al. Effect of CCK-1 antagonist, dexloxiglumide, in female patients with irritable bowel syndrome: a pharmacodynamic and pharmacogenomic study. Am. J. Gastroenterol. 100(3), 652-663 (2005).
32. McWilliams V, Whiteside G, McKeage K. Linaclotide: first global approval. Drugs 72(16), 2167-2175 (2012).
33. Quigley EM, Tack J, Chey WD et al. Randomized clinical trials: linaclotide Phase 3 studies in IBS-C - a prespecified further analysis based on European Medicines Agency-specified endpoints. Aliment. Pharmacol. Ther. 37(1), 49-61 (2013).
34. Wong BS, Camilleri M. Elobixibat for the treatment of constipation. Expert Opin. Investig. Drugs 22(2), 277-284 (2013).
35. Basu N, Arshad N, Visweswariah SS. Receptor guanylyl cyclase C (GC-C): regulation and signal transduction. Mol. Cell. Biochem. 334, 67-80 (2010).
36. Lucas KA, Pitari GM, Kazerounian S et al. Guanylyl cyclases and signaling by cyclic GMP. Pharmacol. Rev. 52, 375-413 (2000).
37. Currie MG, Fok KF, Kato J et al. Guanylin: an endogenous activator of intestinal guanylate cyclase. Proc. Natl Acad. Sci. USA 89, 947-951 (1992).
38. Hamna FK, Forte LR, Eber SL et al. Uroguanylin: structure and activity of a second endogenous peptides that stimulates intestinal guanylate cyclase. Proc. Natl Acad. Sci. USA 90, 10464-10468 (1993).
39. Arshad N, Visweswariah SS. The multiple and enigmatic roles of guanylyl cyclase C in intestinal homeostasis. FEBS Lett. 586(18), 2835-2840 (2012).
40. Forte LR. Uroguanylin and guanylin peptides: pharmacology and experimental therapeutics. Pharmacol. Ther. 104, 137-162 (2004).
41. Lacy BE, Levenick JM, Crowell M. Chronic constipation: new diagnostic and treatment approaches. Ther. Adv. Gastroenterol. 5(4) 233-247 (2012).
42. Harris LA, Crowell MD. Linaclotide, a new direction in the treatment of irritable bowel syndrome and chronic constipation. Curr. Opin. Mol. Ther. 9, 403-410 (2007).
43. Solinga, R., Kessler, M, Busby, R. and Currie, M. A comparison of the physical and pharmacological properties of plecanatide (SP-304) and the human hormone uroguanylin. ACJ 11(S2), 332 (2011).
44. Lin JE, Valentino M, Marszalowicz G et al. Bacterial heat-stable enterotoxins: translation of pathogenic peptides into novel targeted diagnostics and therapeutics. Toxins 2, 2028-2054 (2010).
45. Staples SJ, Asher SE, Giannella RA. Purification and characterization of heat-stable enterotoxin produced by a strain of E. coli pathogenic for man. J. Biol. Chem. 255, 4716-4721 (1980).
46. Yoshimura S, Ikemura H, Watanabe H et al. Essential structure for full enterotoxigenic activity of heat-stable enterotoxin produced by enterotoxigenic Escherichia coli. FEBS Lett. 181, 138-142 (1985).
47. Waldmann SA, O'Hanley P. Influence of a glycine or proline substitution on the functional properties of a 14-amino-acid analog of Escherichia coli heat-satble enterotoxin. Infect. Immun. 57, 2420-2424 (1989).
48. Matecko, I, Burmann BM, Schweimer K et al. Structural characterization of the E. coli heat stable enterotoxin STh. Open Spectrosc. J. 2, 34-39 (2008).
49. Carpick, BW, Gariepy J. Structural characterization of functionally important regions of the Escherichia coli heat-stable enterotoxin ST1b. Biochemistry 30, 4803-4809 (1991).
50. Skelton NJ, Garcia KC, Goeddel DV, Quan C, Burnier JP. Determination of the solution structure of the peptide hormone guanylin: observation of a novel form of topological stereoisomerism. Biochemistry 33, 13581-13592 (1994).
51. Marx UC, Klodt J, Meyer M et al. One peptide, two topologies: structure and interconversion dynamics of human uroguanylin isomers. J. Pept. Res. 52, 229-240 (1998).
52. Weiglmeier PR, Rösch P, Berkner H. Cure and curse: E. coli heat-stable enterotoxin and its receptor guanylyl cyclase C. Toxins 2, 2213-2229 (2010).
53. Gariépy J, Judd AK, Schoolnik GK. Importance of disulfide bridges in the structure and activity of Escherichia coli enterotoxin ST1b. Proc. Natl Acad. Sci. USA 84, 8907-8911 (1987).
54. Carpick BW, Gariepy J. The Escherichia coli heat-stable enterotoxin is a long-lived superagonist of guanylin. Infect. Immun. 61, 4710-4715 (1993).
55. Hamra FK, Eber SL, Chin DT, Currie MG, Forte LR. Regulation of intestinal uroguanylin/guanylin receptor-mediated responses by mucosal acidity. Proc. Natl Acad. Sci. USA 94, 2705-2710 (1997).
56. Bryant AP, Busby RW, Bartolini WP et al. Linaclotide is a potent and selective guanylate cyclase C agonist that elicits pharmacological effects locally in the gastrointestinal tract. Life Sci. 86, 760-765 (2010).
57. Busby RW, Bryant AP, Bartolini WP et al. Linaclotide, through activation of guanylate cyclase C, acts locally in the gastrointestinal tract to elicit enhanced intestinal secretion and transit. Eur. J. Pharmacol. 649, 328-335 (2010).
58. Kessler MM, Busby RW, Wakefield JD et al. Rat intestinal metabolism of linaclotide, a therapeutic agent in clinical development for the treatment of IBS-C and chronic constipation. Drug Metab. Rev. 40(Suppl. 3) 213-214 (2008).
59. Bryant AP, Busby RW, Cordero EA. MD-1100, a therapeutic agent in development for the treatment of IBS-C, enhances intestinal secretion and transit, decreases visceral pain and is minimally absorbed in rats. Gastroenterology 128, 464 (2005).
60. Eutamene H, Bradesi S, Larauche M et al. Guanylate cyclase C-mediated antinociceptive effects of linaclotide in rodent models of visceral pain. Neurogastroenterol. Motil. 22, 312-e84 (2010).
61. Johnston JM, Kurtz CB, MacDougall JE et al. Linaclotide improves abdominal pain and bowel habits in a Phase 2b study of patients with irritable bowel syndrome with constipation. Gastroenterology 139, 1877-1886 (2010).
62. Ustinova E, Reza T, Currie M, Pezzone M. Oral cyclic guanosine monophosphate (cGMP) desensitizes colonic afferents in an animal model of experimental colitis. Am. J. Gastroenterol. 103(Suppl. 1), S187 (2008).
63. Jin J, Sklar GE, Min Sen Oh V, Chuen Li S. Factors affecting therapeutic compliance: a review from the patient's perspective. Ther. Clin. Risk. Manag. 4(1), 269-286 (2008).
64. Soltero R. Oral protein and peptide drug delivery. In: Drug Delivery Principles and Applications. Wang B, Siahaan T, Soltero, R (Eds). Wiley and Sons, Inc. Publications, NJ, USA, 189-200 (2005).
65. Antosova Z, Mackova M, Kral V, Macek T. Therapeutic application of peptides and proteins: parenteral forever? Trends Biotechnol. 27(11) 628-635 (2009).
66. Cheek S, Krishna SS, Grishin NV. Structural classification of small, disulfide-rich protein domains. J. Mol. Biol. 359, 215-237 (2006).
67. Ireland DC, Clark RJ, Daly NL, Craik DJ. Isolation, sequencing, and structure-activity relationships of cyclotides. J. Nat. Prod. 73, 1610-1622 (2010).
68. King GF. Venoms as a platform for human drugs: translating toxins into therapeutics. Expert Opin. Biol. Ther. 11, 1469-1484 (2011).
69. King GF, Hardy MC. Spider-venom peptides: structure, pharmacology, and potential for control of insect pests. Annu. Rev. Entomol. 58, 475-496 (2013).
70. Teichert RW, Jimenez EC, Olivera BM. Biology and Pharmacology of Conotoxins. In: Botulinum Toxin: Therapeutic Clinical Practice and Science. Elsevier Inc., PA, USA (2009).
71. Halai R, Craik DJ. Conotoxins: natural product drug leads. Nat. Prod. Rep. 26, 526-536 (2009).
72. Dubreuil JD. The Comprehensive Sourcebook of Bacterial Protein Toxins. Elsevier Ltd, London, UK, 798-817 (2006).
73. Ganz T. Defensins: antimicrobial peptides of innate immunity. Nat. Rev. Immunol. 3, 710-720 (2003).
74. Moore SJ, Leung CL, Cochran Jr. Knottins: disulfide-bonded therapeutic and diagnostic peptides. Drug Discov. Today: Tech. 9, e3-e11 (2012).
75. Craik DJ, Clark RJ. Daly NL. Cyclotides and conotoxins ultra-stable disulfide-rich peptides. Chim. Oggi. 26(4), 20-22 (2008).
76. Cain C. Excited about cycling. BioCentury 20(38), 7-25 (2012).
77. Fiskerstrand T, Arshad N, Haukanes BI et al. Familial diarrhea syndrome caused by an activating GUCY2C mutation. N. Engl. J. Med. 366, 1586-1595 (2012).
78. US FDA announcement. www.fda.gov/NewsEvents/Newsroom/ PressAnnouncements/ucm317505.htm
79. European Medicines Agency announcement. www.ema.europa.eu/ema/index. jsp?curl=pages/medicines/human/ medicines/002490/smops/Positive/ human-smop-000414. jsp&mid=WC0b01ac058001d127
80. Decision Resources Group. www.decisionresources.com/News-and- Events/Press-Releases/irritable-bowel-syndrome-050912
81. Hanmi Pharmaceuticals Co. Ltd, Global Licensing-Out. www.hanmipharm.com/ eng/business/ global-out01.asp
82. Dainippon Sumitomo Pharma. Profile of major products under development (as of October 31 2012). www.ds-pharma.com/rd/clinical/pipeline- profile.html
83. Synergy Pharmaceuticals: compounds in development. www.synergypharma.com/ pipeline/overview
84. The plecanatide Chronic Idiopathic Constipation (CIC) study. www.clinicaltrials.gov/show/NCT01429987
85. The plecanatide irritable bowel syndrome with constipation study (IBS-C) (CIBS). www.clinicaltrials.gov/show/NCT01722318
86. Ardelyx RDX5791. http://ardelyx.com/rdx5791
87. A study to evaluate the safety and efficacy of RDX5791 for the treatment of constipation predominant irritable bowel syndrome (IBS-C). http://clinicaltrials.gov/show/ NCT01340053
88. Thomson Reuters Integrity. Prous Science. http://integrity.thomson- pharma.com