Ibodutant | MEN-15596 | CAS#522664-63-7 | NK2 antagonist

MedKoo Cat#: 319890 | Name: Ibodutant

Description:

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

Ibodutant (MEN-15596) is a selective, potent, and orally active antagonist of the neurokinin-2 (NK2) receptor, developed primarily for the treatment of gastrointestinal disorders such as irritable bowel syndrome with diarrhea (IBS-D). It exhibits high affinity for the human NK2 receptor with a reported Ki of 0.29 nM, and functions by blocking neurokinin A-mediated smooth muscle contraction and visceral hypersensitivity. In preclinical studies, ibodutant effectively reduced colonic motility and abdominal pain in animal models.

Chemical Structure

Ibodutant

CAS#522664-63-7

Theoretical Analysis

MedKoo Cat#: 319890

Name: Ibodutant

CAS#: 522664-63-7

Chemical Formula: C37H48N4O4S

Exact Mass: 644.3396

Molecular Weight: 644.88

Elemental Analysis: C, 68.91; H, 7.50; N, 8.69; O, 9.92; S, 4.97

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

MEN-15596; MEN 15596; MEN15596; Ibodutant;

IUPAC/Chemical Name

(R)-6-methyl-N-(1-((1-oxo-3-phenyl-1-(((1-((tetrahydro-2H-pyran-4-yl)methyl)piperidin-4-yl)methyl)amino)propan-2-yl)carbamoyl)cyclopentyl)benzo[b]thiophene-2-carboxamide

InChi Key

YQYSVMKCMIUCHY-WJOKGBTCSA-N

InChi Code

InChI=1S/C37H48N4O4S/c1-26-9-10-30-23-33(46-32(30)21-26)35(43)40-37(15-5-6-16-37)36(44)39-31(22-27-7-3-2-4-8-27)34(42)38-24-28-11-17-41(18-12-28)25-29-13-19-45-20-14-29/h2-4,7-10,21,23,28-29,31H,5-6,11-20,22,24-25H2,1H3,(H,38,42)(H,39,44)(H,40,43)/t31-/m1/s1

SMILES Code

O=C(C1=CC2=CC=C(C)C=C2S1)NC3(C(N[C@H](CC4=CC=CC=C4)C(NCC5CCN(CC6CCOCC6)CC5)=O)=O)CCCC3

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, not in water

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 644.88 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

1: Bellucci F, Buéno L, Bugianesi R, Crea A, D'Aranno V, Meini S, Santicioli P, Tramontana M, Maggi CA. Gender related differential effect of tachykinin NK2 receptor-mediated visceral hyperalgesia in guinea pig colon. Br J Pharmacol. 2016 Jan 13. doi: 10.1111/bph.13427. [Epub ahead of print] PubMed PMID: 26758701. 2: Corsetti M, Akyuz F, Tack J. Targeting tachykinin receptors for the treatment of functional gastrointestinal disorders with a focus on irritable bowel syndrome. Neurogastroenterol Motil. 2015 Oct;27(10):1354-70. doi: 10.1111/nmo.12616. Epub 2015 Jun 18. Review. PubMed PMID: 26088804. 3: Santicioli P, Meini S, Giuliani S, Lecci A, Maggi CA. Antagonist profile of ibodutant at the tachykinin NK(2) receptor in guinea pig isolated bronchi. Eur J Pharmacol. 2013 Oct 24. pii: S0014-2999(13)00788-7. doi: 10.1016/j.ejphar.2013.10.029. [Epub ahead of print] PubMed PMID: 24513513. 4: Santicioli P, Meini S, Giuliani S, Lecci A, Maggi CA. Antagonist profile of ibodutant at the tachykinin NK(2) receptor in guinea pig isolated bronchi. Eur J Pharmacol. 2013 Nov 15;720(1-3):180-5. PubMed PMID: 24436990. 5: Mearin F, Rey E, Balboa A. [Functional and motor digestive disorders]. Gastroenterol Hepatol. 2013 Oct;36 Suppl 2:3-14. doi: 10.1016/S0210-5705(13)70048-7. Spanish. PubMed PMID: 24160947. 6: Sia TC, Brookes SJ, Dinning PG, Wattchow DA, Spencer NJ. Peristalsis and propulsion of colonic content can occur after blockade of major neuroneuronal and neuromuscular transmitters in isolated guinea pig colon. Am J Physiol Gastrointest Liver Physiol. 2013 Dec;305(12):G933-9. doi: 10.1152/ajpgi.00257.2013. Epub 2013 Oct 10. PubMed PMID: 24113766. 7: Santicioli P, Meini S, Giuliani S, Catalani C, Bechi P, Riccadonna S, Ringressi MN, Maggi CA. Characterization of ibodutant at NK(2) receptor in human colon. Eur J Pharmacol. 2013 Feb 28;702(1-3):32-7. doi: 10.1016/j.ejphar.2013.01.021. Epub 2013 Jan 29. PubMed PMID: 23376417. 8: Cipriani G, Santicioli P, Evangelista S, Maggi CA, Riccadonna S, Ringressi MN, Bechi P, Faussone-Pellegrini MS, Vannucchi MG. Effect of otilonium bromide and ibodutant on the internalization of the NK2 receptor in human colon. Neurogastroenterol Motil. 2011 Jan;23(1):96-102, e10. doi: 10.1111/j.1365-2982.2010.01594.x. PubMed PMID: 20879991. 9: Gensini M, Altamura M, Dimoulas T, Fedi V, Giannotti D, Giuliani S, Guidi A, Harmat NJ, Meini S, Nannicini R, Pasqui F, Tramontana M, Triolo A, Maggi CA. Modulation on C- and N-terminal moieties of a series of potent and selective linear tachykinin NK(2) receptor antagonists. ChemMedChem. 2010 Jan;5(1):65-78. doi: 10.1002/cmdc.200900389. PubMed PMID: 19957262. 10: Meini S, Bellucci F, Catalani C, Cucchi P, Giolitti A, Santicioli P, Giuliani S. Multifaceted approach to determine the antagonist molecular mechanism and interaction of ibodutant ([1-(2-phenyl-1R-[[1-(tetrahydropyran-4-ylmethyl)-piperidin-4-ylmethyl]-carbamoyl ]-ethylcarbamoyl)-cyclopentyl]-amide) at the human tachykinin NK2 receptor. J Pharmacol Exp Ther. 2009 May;329(2):486-95. doi: 10.1124/jpet.108.150201. Epub 2009 Feb 13. PubMed PMID: 19218528.