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MedKoo Cat#: 598032 | Name: Linaclotide acetate

Description:

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

Linaclotide acetate is an oral guanylate cyclase C agonist linaclotide; 14 amino acid peptide for the potential treatment of constipation-predominant irritable bowel syndrome and chronic idiopathic constipation.

Chemical Structure

Linaclotide acetate
Linaclotide acetate
CAS#851199-60-5

Theoretical Analysis

MedKoo Cat#: 598032

Name: Linaclotide acetate

CAS#: 851199-60-5

Chemical Formula: C61H83N15O23S6

Exact Mass:

Molecular Weight: 1586.77

Elemental Analysis: C, 46.17; H, 5.27; N, 13.24; O, 23.19; S, 12.12

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
851199-59-2 (free)
Synonym
Linaclotide acetate; MM-416775; MM 416775; MM416775 MD-1100 acetate; Linzess;
IUPAC/Chemical Name
((3S,6R,9S,15R,20R,23S,26S,29R,32R,37R,40S,45aS)-32-amino-40-(2-amino-2-oxoethyl)-26-(2-carboxyethyl)-23-(4-hydroxybenzyl)-9-((R)-1-hydroxyethyl)-3-methyl-1,4,7,10,13,22,25,28,31,38,41,47-dodecaoxotetracontahydro-19H-37,20-(epiminomethano)-6,29-(methanodithiomethano)pyrrolo[2,1-s][1,2,27,28]tetrathia[5,8,11,14,17,20,23,32,35,38,41]undecaazacyclotritetracontine-15-carbonyl)-L-tyrosine compound with acetic acid (1:1)
InChi Key
KWFNVZFWXXEJKL-YZDVLOIKSA-N
InChi Code
InChI=1S/C59H79N15O21S6.C2H4O2/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29;1-2(3)4/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95);1H3,(H,3,4)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-;/m0./s1
SMILES Code
C[C@H]1C(N[C@H]2CSSC[C@H]3C(N[C@@H](CCC(O)=O)C(N[C@@H](Cc4ccc(O)cc4)C(N[C@H](C(N[C@H](C(N[C@@H](CC(N)=O)C(N5CCC[C@H]5C(N1)=O)=O)=O)CSSC[C@H](N)C(N3)=O)=O)CSSC[C@@H](C(N[C@H](C(O)=O)Cc6ccc(O)cc6)=O)NC(CNC([C@H]([C@H](O)C)NC2=O)=O)=O)=O)=O)=O)=O.CC(O)=O
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,586.77 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
1: Layer P, Stanghellini V. Review article: Linaclotide for the management of irritable bowel syndrome with constipation. Aliment Pharmacol Ther. 2014 Feb;39(4):371-84. doi: 10.1111/apt.12604. Epub 2014 Jan 16. Review. PubMed PMID: 24433216; PubMed Central PMCID: PMC4305214. 2: Lacy BE, Schey R, Shiff SJ, Lavins BJ, Fox SM, Jia XD, Blakesley RE, Hao X, Cronin JA, Currie MG, Kurtz CB, Johnston JM, Lembo AJ. Linaclotide in Chronic Idiopathic Constipation Patients with Moderate to Severe Abdominal Bloating: A Randomized, Controlled Trial. PLoS One. 2015 Jul 29;10(7):e0134349. doi: 10.1371/journal.pone.0134349. eCollection 2015. PubMed PMID: 26222318; PubMed Central PMCID: PMC4519259. 3: Castro J, Harrington AM, Hughes PA, Martin CM, Ge P, Shea CM, Jin H, Jacobson S, Hannig G, Mann E, Cohen MB, MacDougall JE, Lavins BJ, Kurtz CB, Silos-Santiago I, Johnston JM, Currie MG, Blackshaw LA, Brierley SM. Linaclotide inhibits colonic nociceptors and relieves abdominal pain via guanylate cyclase-C and extracellular cyclic guanosine 3',5'-monophosphate. Gastroenterology. 2013 Dec;145(6):1334-46.e1-11. doi: 10.1053/j.gastro.2013.08.017. Epub 2013 Aug 16. PubMed PMID: 23958540. 4: Love BL, Johnson A, Smith LS. Linaclotide: a novel agent for chronic constipation and irritable bowel syndrome. Am J Health Syst Pharm. 2014 Jul 1;71(13):1081-91. doi: 10.2146/ajhp130575. Review. PubMed PMID: 24939497. 5: Rao SS, Quigley EM, Shiff SJ, Lavins BJ, Kurtz CB, MacDougall JE, Currie MG, Johnston JM. Effect of linaclotide on severe abdominal symptoms in patients with irritable bowel syndrome with constipation. Clin Gastroenterol Hepatol. 2014 Apr;12(4):616-23. doi: 10.1016/j.cgh.2013.09.022. Epub 2013 Sep 25. PubMed PMID: 24075889. 6: Lembo AJ, Schneier HA, Shiff SJ, Kurtz CB, MacDougall JE, Jia XD, Shao JZ, Lavins BJ, Currie MG, Fitch DA, Jeglinski BI, Eng P, Fox SM, Johnston JM. Two randomized trials of linaclotide for chronic constipation. N Engl J Med. 2011 Aug 11;365(6):527-36. doi: 10.1056/NEJMoa1010863. PubMed PMID: 21830967. 7: McCormack PL. Linaclotide: a review of its use in the treatment of irritable bowel syndrome with constipation. Drugs. 2014 Jan;74(1):53-60. doi: 10.1007/s40265-013-0157-5. Review. PubMed PMID: 24293117. 8: Kang SB, Marchelletta RR, Penrose H, Docherty MJ, McCole DF. A comparison of linaclotide and lubiprostone dosing regimens on ion transport responses in human colonic mucosa. Pharmacol Res Perspect. 2015 Mar;3(2):e00128. doi: 10.1002/prp2.128. Epub 2015 Mar 13. PubMed PMID: 26038704; PubMed Central PMCID: PMC4448989. 9: Chey WD, Lembo AJ, Lavins BJ, Shiff SJ, Kurtz CB, Currie MG, MacDougall JE, Jia XD, Shao JZ, Fitch DA, Baird MJ, Schneier HA, Johnston JM. Linaclotide for irritable bowel syndrome with constipation: a 26-week, randomized, double-blind, placebo-controlled trial to evaluate efficacy and safety. Am J Gastroenterol. 2012 Nov;107(11):1702-12. PubMed PMID: 22986437. 10: Rao S, Lembo AJ, Shiff SJ, Lavins BJ, Currie MG, Jia XD, Shi K, MacDougall JE, Shao JZ, Eng P, Fox SM, Schneier HA, Kurtz CB, Johnston JM. A 12-week, randomized, controlled trial with a 4-week randomized withdrawal period to evaluate the efficacy and safety of linaclotide in irritable bowel syndrome with constipation. Am J Gastroenterol. 2012 Nov;107(11):1714-24; quiz p.1725. PubMed PMID: 22986440; PubMed Central PMCID: PMC3504311. 11: Linaclotide. A bacterial enterotoxin derivative with a laxative action, nothing more. Prescrire Int. 2014 Dec;23(155):285-8. PubMed PMID: 25629140. 12: Lacy BE, Lembo AJ, Macdougall JE, Shiff SJ, Kurtz CB, Currie MG, Johnston JM. Responders vs clinical response: a critical analysis of data from linaclotide phase 3 clinical trials in IBS-C. Neurogastroenterol Motil. 2014 Mar;26(3):326-33. doi: 10.1111/nmo.12264. Epub 2013 Dec 30. PubMed PMID: 24382134; PubMed Central PMCID: PMC4282394. 13: Atluri DK, Chandar AK, Bharucha AE, Falck-Ytter Y. Effect of linaclotide in irritable bowel syndrome with constipation (IBS-C): a systematic review and meta-analysis. Neurogastroenterol Motil. 2014 Apr;26(4):499-509. doi: 10.1111/nmo.12292. Epub 2013 Dec 18. Review. PubMed PMID: 24351035. 14: Rothstein RD, Friedenberg FK. Linaclotide: a novel compound for the treatment of irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2013 Oct;14(15):2125-32. doi: 10.1517/14656566.2013.833605. Epub 2013 Sep 5. Review. PubMed PMID: 24007408. 15: Tchernychev B, Ge P, Kessler MM, Solinga RM, Wachtel D, Tobin JV, Thomas SR, Lunte CE, Fretzen A, Hannig G, Bryant AP, Kurtz CB, Currie MG, Silos-Santiago I. MRP4 Modulation of the Guanylate Cyclase-C/cGMP Pathway: Effects on Linaclotide-Induced Electrolyte Secretion and cGMP Efflux. J Pharmacol Exp Ther. 2015 Oct;355(1):48-56. doi: 10.1124/jpet.115.224329. Epub 2015 Jul 27. PubMed PMID: 26216942. 16: Sayuk GS. Linaclotide: promising IBS-C efficacy in an era of provisional study endpoints. Am J Gastroenterol. 2012 Nov;107(11):1726-9. doi: 10.1038/ajg.2012.325. PubMed PMID: 23160292; PubMed Central PMCID: PMC3957218. 17: Corsetti M, Tack J. Linaclotide: A new drug for the treatment of chronic constipation and irritable bowel syndrome with constipation. United European Gastroenterol J. 2013 Feb;1(1):7-20. doi: 10.1177/2050640612474446. PubMed PMID: 24917937; PubMed Central PMCID: PMC4040778. 18: Carballo F. Linaclotide in the treatment of patients with irritable bowel syndrome and constipation - analysis of an opportunity. Rev Esp Enferm Dig. 2013 Jul;105(6):345-54. Review. PubMed PMID: 24090017. 19: Wensel TM, Luthin DR. Linaclotide: a novel approach to the treatment of irritable bowel syndrome. Ann Pharmacother. 2011 Dec;45(12):1535-43. doi: 10.1345/aph.1Q428. Epub 2011 Nov 1. Review. PubMed PMID: 22045908. 20: Huang H, Taylor DC, Carson RT, Sarocco P, Friedman M, Munsell M, Blum SI, Menzin J. Economic Evaluation of Linaclotide for the Treatment of Adult Patients With Chronic Idiopathic Constipation in the United States. Manag Care. 2016 Feb;25(2):41-8. PubMed PMID: 27008836.