MedKoo Cat#: 126238 | Name: Ulimorelin hydrochloride monohydrate

Description:

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

Ulimorelin, also known as TZP-101, is a GHS receptor agonist potentially for the treatment of postoperative ileus and gastrointestinal disorders. TZP-101 accelerates gastric emptying in adults with diabetes and symptomatic gastroparesis. TZP-101 relieves gastroparesis associated with severe nausea and vomiting. TZP-101/ulimorelin accelerates gastrointestinal recovery independently of opioid use and surgery type.

Chemical Structure

Ulimorelin hydrochloride monohydrate
Ulimorelin hydrochloride monohydrate
CAS#951326-02-6 (H2O)

Theoretical Analysis

MedKoo Cat#: 126238

Name: Ulimorelin hydrochloride monohydrate

CAS#: 951326-02-6 (H2O)

Chemical Formula: C30H42ClFN4O5

Exact Mass: 592.2828

Molecular Weight: 593.14

Elemental Analysis: C, 60.75; H, 7.14; Cl, 5.98; F, 3.20; N, 9.45; O, 13.49

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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Synonym
ULIMORELIN HYDROCHLORIDE; Ulimorelin hydrochloride monohydrate; Ulimorelin; TZP-101; TZP 101; TZP101
IUPAC/Chemical Name
(2R,5S,8R,11R)-5-cyclopropyl-11-(4-fluorobenzyl)-2,7,8-trimethyl-4,5,7,8,10,11,13,14,15,16-decahydro-2H-benzo[q][1]oxa[4,7,10,13]tetraazacyclooctadecine-6,9,12(3H)-trione hydrochloride hydrate
InChi Key
ZWIXEQBDJMFCMN-DHHNQDMHSA-N
InChi Code
InChI=1S/C30H39FN4O4.ClH.H2O/c1-19-18-33-27(23-12-13-23)30(38)35(3)20(2)28(36)34-25(17-21-10-14-24(31)15-11-21)29(37)32-16-6-8-22-7-4-5-9-26(22)39-19;;/h4-5,7,9-11,14-15,19-20,23,25,27,33H,6,8,12-13,16-18H2,1-3H3,(H,32,37)(H,34,36);1H;1H2/t19-,20-,25-,27+;;/m1../s1
SMILES Code
O.Cl.C[C@@H]1CN[C@@H](C2CC2)C(=O)N(C)[C@H](C)C(=O)N[C@H](CC3=CC=C(F)C=C3)C(=O)NCCCC4=C(O1)C=CC=C4
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 593.14 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: Barboza JL, Okun MS, Moshiree B. The treatment of gastroparesis, constipation and small intestinal bacterial overgrowth syndrome in patients with Parkinson's disease. Expert Opin Pharmacother. 2015;16(16):2449-64. doi: 10.1517/14656566.2015.1086747. Epub 2015 Sep 16. Review. PubMed PMID: 26374094. 2: Shin A, Wo JM. Therapeutic applications of ghrelin agonists in the treatment of gastroparesis. Curr Gastroenterol Rep. 2015 Feb;17(2):430. doi: 10.1007/s11894-015-0430-8. Review. PubMed PMID: 25702264. 3: Broad J, Callaghan B, Sanger GJ, Brock JA, Furness JB. Analysis of the ghrelin receptor-independent vascular actions of ulimorelin. Eur J Pharmacol. 2015 Apr 5;752:34-9. doi: 10.1016/j.ejphar.2015.02.005. Epub 2015 Feb 14. PubMed PMID: 25687251. 4: Callaghan B, Kosari S, Pustovit RV, Sartor DM, Ferens D, Ban K, Baell J, Nguyen TV, Rivera LR, Brock JA, Furness JB. Hypotensive effects of ghrelin receptor agonists mediated through a novel receptor. Br J Pharmacol. 2014 Mar;171(5):1275-86. doi: 10.1111/bph.12527. PubMed PMID: 24670149; PubMed Central PMCID: PMC3952804. 5: Sanger GJ. Ghrelin and motilin receptor agonists: time to introduce bias into drug design. Neurogastroenterol Motil. 2014 Feb;26(2):149-55. doi: 10.1111/nmo.12300. Review. PubMed PMID: 24438586. 6: Pustovit RV, Callaghan B, Kosari S, Rivera LR, Thomas H, Brock JA, Furness JB. The mechanism of enhanced defecation caused by the ghrelin receptor agonist, ulimorelin. Neurogastroenterol Motil. 2014 Feb;26(2):264-71. doi: 10.1111/nmo.12259. Epub 2013 Nov 7. PubMed PMID: 24304447. 7: Shaw M, Pediconi C, McVey D, Mondou E, Quinn J, Chamblin B, Rousseau F. Safety and efficacy of ulimorelin administered postoperatively to accelerate recovery of gastrointestinal motility following partial bowel resection: results of two randomized, placebo-controlled phase 3 trials. Dis Colon Rectum. 2013 Jul;56(7):888-97. doi: 10.1097/DCR.0b013e31829196d0. PubMed PMID: 23739196. 8: Hoveyda HR, Marsault E, Gagnon R, Mathieu AP, Vézina M, Landry A, Wang Z, Benakli K, Beaubien S, Saint-Louis C, Brassard M, Pinault JF, Ouellet L, Bhat S, Ramaseshan M, Peng X, Foucher L, Beauchemin S, Bhérer P, Veber DF, Peterson ML, Fraser GL. Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (Part I): Development of ulimorelin (TZP-101) from hit to clinic. J Med Chem. 2011 Dec 22;54(24):8305-20. doi: 10.1021/jm2007062. Epub 2011 Nov 22. PubMed PMID: 22106937. 9: Bochicchio G, Charlton P, Pezzullo JC, Kosutic G, Senagore A. Ghrelin agonist TZP-101/ulimorelin accelerates gastrointestinal recovery independently of opioid use and surgery type: covariate analysis of phase 2 data. World J Surg. 2012 Jan;36(1):39-45. doi: 10.1007/s00268-011-1335-9. PubMed PMID: 22072430; PubMed Central PMCID: PMC3243849. 10: Greenwood-Van Meerveld B, Kriegsman M, Nelson R. Ghrelin as a target for gastrointestinal motility disorders. Peptides. 2011 Nov;32(11):2352-6. doi: 10.1016/j.peptides.2011.03.014. Epub 2011 Mar 29. Review. PubMed PMID: 21453735. 11: Wo JM, Ejskjaer N, Hellström PM, Malik RA, Pezzullo JC, Shaughnessy L, Charlton P, Kosutic G, McCallum RW. Randomised clinical trial: ghrelin agonist TZP-101 relieves gastroparesis associated with severe nausea and vomiting--randomised clinical study subset data. Aliment Pharmacol Ther. 2011 Mar;33(6):679-88. doi: 10.1111/j.1365-2036.2010.04567.x. Epub 2011 Jan 7. PubMed PMID: 21214610. 12: Ejskjaer N, Dimcevski G, Wo J, Hellström PM, Gormsen LC, Sarosiek I, Søfteland E, Nowak T, Pezzullo JC, Shaughnessy L, Kosutic G, McCallum R. Safety and efficacy of ghrelin agonist TZP-101 in relieving symptoms in patients with diabetic gastroparesis: a randomized, placebo-controlled study. Neurogastroenterol Motil. 2010 Oct;22(10):1069-e281. doi: 10.1111/j.1365-2982.2010.01519.x. Epub 2010 Jun 28. PubMed PMID: 20524987. 13: Semple G. Molecular Medicine - CHI's 17th International Tri-Conference: Mastering Medicinal Chemistry - CHI's Seventh Annual Conference. IDrugs. 2010 Apr;13(4):214-8. PubMed PMID: 20373246. 14: Popescu I, Fleshner PR, Pezzullo JC, Charlton PA, Kosutic G, Senagore AJ. The Ghrelin agonist TZP-101 for management of postoperative ileus after partial colectomy: a randomized, dose-ranging, placebo-controlled clinical trial. Dis Colon Rectum. 2010 Feb;53(2):126-34. doi: 10.1007/DCR.0b013e3181b54166. PubMed PMID: 20087086. 15: Gater D, Macauley D. American Chemical Society--238th National Meeting & Exposition. Developments in medicinal chemistry: part 1. 16-20 August 2009, Washington DC, USA. IDrugs. 2009 Oct;12(10):605-7. PubMed PMID: 19790004. 16: Wargin W, Thomas H, Clohs L, St-Louis C, Ejskjaer N, Gutierrez M, Shaughnessy L, Kosutic G. Contribution of protein binding to the pharmacokinetics of the ghrelin receptor agonist TZP-101 in healthy volunteers and adults with symptomatic gastroparesis: two randomized, double-blind studies and a binding profile study. Clin Drug Investig. 2009;29(6):409-18. doi: 10.2165/00044011-200929060-00004. PubMed PMID: 19432500. 17: Ejskjaer N, Vestergaard ET, Hellström PM, Gormsen LC, Madsbad S, Madsen JL, Jensen TA, Pezzullo JC, Christiansen JS, Shaughnessy L, Kosutic G. Ghrelin receptor agonist (TZP-101) accelerates gastric emptying in adults with diabetes and symptomatic gastroparesis. Aliment Pharmacol Ther. 2009 Jun 1;29(11):1179-87. doi: 10.1111/j.1365-2036.2009.03986.x. Epub 2009 Feb 27. PubMed PMID: 19298585. 18: Fraser GL, Venkova K, Hoveyda HR, Thomas H, Greenwood-Van Meerveld B. Effect of the ghrelin receptor agonist TZP-101 on colonic transit in a rat model of postoperative ileus. Eur J Pharmacol. 2009 Feb 14;604(1-3):132-7. doi: 10.1016/j.ejphar.2008.12.011. Epub 2008 Dec 14. PubMed PMID: 19121631. 19: Fraser GL, Hoveyda HR, Tannenbaum GS. Pharmacological demarcation of the growth hormone, gut motility and feeding effects of ghrelin using a novel ghrelin receptor agonist. Endocrinology. 2008 Dec;149(12):6280-8. doi: 10.1210/en.2008-0804. Epub 2008 Aug 21. PubMed PMID: 18719021. 20: Lasseter KC, Shaughnessy L, Cummings D, Pezzullo JC, Wargin W, Gagnon R, Oliva J, Kosutic G. Ghrelin agonist (TZP-101): safety, pharmacokinetics and pharmacodynamic evaluation in healthy volunteers: a phase I, first-in-human study. J Clin Pharmacol. 2008 Feb;48(2):193-202. doi: 10.1177/0091270007310380. PubMed PMID: 18199894.