Ibodutant

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

MedKoo CAT#: 319890

CAS#: 522664-63-7

Description: Ibodutant, also known as MEN-15596, is a tachykinin receptor antagonist under development for irritable bowel syndrome diarrhea. Ibodutant selectively blocks the tachykinin receptor NK2, with blockade practically complete in nanomolar concentrations.


Price and Availability

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Ibodutant is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319890
Name: Ibodutant
CAS#: 522664-63-7
Chemical Formula: C37H48N4O4S
Exact Mass: 644.3396
Molecular Weight: 644.875
Elemental Analysis: C, 68.91; H, 7.50; N, 8.69; O, 9.92; S, 4.97


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


Technical Data

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).

Harmonized System Code:
293490


References

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.