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MedKoo Cat#: 414337 | Name: Nepadutant

Description:

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

Nepadutant is a glycosylated bicyclic cyclo​hexapeptide drug which acts as a highly selective NK2 receptor antagonist.

Chemical Structure

Nepadutant
Nepadutant
CAS#183747-35-5

Theoretical Analysis

MedKoo Cat#: 414337

Name: Nepadutant

CAS#: 183747-35-5

Chemical Formula: C45H58N10O13

Exact Mass: 946.4185

Molecular Weight: 947.02

Elemental Analysis: C, 57.07; H, 6.17; N, 14.79; O, 21.96

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 #
No Data
Synonym
Nepadutant; MEN11,420; MEN 11,420; MEN-11,420; MEN11420; MEN-11420; MEN 11420
IUPAC/Chemical Name
2-((1S,4S,7S,10S,13S,16S)-7-((1H-indol-3-yl)methyl)-4-benzyl-16-isobutyl-3,6,9,12,15,18,21-heptaoxo-2,5,8,11,14,17,20-heptaazabicyclo[8.8.4]docosan-13-yl)-N-((2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamide
InChi Key
NGCNKEZHGRXHNL-WVWQGFTISA-N
InChi Code
InChI=1S/C45H58N10O13/c1-21(2)13-27-39(62)53-31(17-35(59)55-45-36(48-22(3)57)38(61)37(60)33(20-56)68-45)43(66)52-30-16-34(58)47-19-32(44(67)49-27)54-40(63)28(14-23-9-5-4-6-10-23)50-41(64)29(51-42(30)65)15-24-18-46-26-12-8-7-11-25(24)26/h4-12,18,21,27-33,36-38,45-46,56,60-61H,13-17,19-20H2,1-3H3,(H,47,58)(H,48,57)(H,49,67)(H,50,64)(H,51,65)(H,52,66)(H,53,62)(H,54,63)(H,55,59)/t27-,28-,29-,30-,31-,32-,33+,36+,37+,38+,45+/m0/s1
SMILES Code
CC(C[C@@H]1NC([C@@H]2CNC(C[C@@H](C(N[C@H](C(N[C@H](C(N2)=O)Cc3ccccc3)=O)Cc(c[nH]4)c5c4cccc5)=O)NC([C@@H](NC1=O)CC(N[C@@H]6O[C@@H]([C@H]([C@@H]([C@H]6NC(C)=O)O)O)CO)=O)=O)=O)=O)C
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
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 947.02 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: Ahluwalia A. Nepadutant Menarini Richerche. Curr Opin Investig Drugs. 2001 Jul;2(7):919-22. PMID: 11757791. 2: Lecci A, Carini F, Tramontana M, D'Aranno V, Marinoni E, Crea A, Bueno L, Fioramonti J, Criscuoli M, Giuliani S, Maggi CA. Nepadutant pharmacokinetics and dose-effect relationships as tachykinin NK2 receptor antagonist are altered by intestinal inflammation in rodent models. J Pharmacol Exp Ther. 2001 Oct;299(1):247-54. PMID: 11561086. 3: Patacchini R, Giuliani S, Turini A, Navarra G, Maggi CA. Effect of nepadutant at tachykinin NK(2) receptors in human intestine and urinary bladder. Eur J Pharmacol. 2000 Jun 23;398(3):389-97. doi: 10.1016/s0014-2999(00)00346-0. PMID: 10862829. 4: Birder LA, Kiss S, de Groat WC, Lecci A, Maggi CA. Effect of nepadutant, a neurokinin 2 tachykinin receptor antagonist, on immediate-early gene expression after trinitrobenzenesulfonic acid-induced colitis in the rat. J Pharmacol Exp Ther. 2003 Jan;304(1):272-6. doi: 10.1124/jpet.102.042077. PMID: 12490601. 5: Cutrufo C, Evangelista S, Cirillo R, Ciucci A, Conte B, Lopez G, Manzini S, Maggi CA. Protective effect of the tachykinin NK2 receptor antagonist nepadutant in acute rectocolitis induced by diluted acetic acid in guinea-pigs. Neuropeptides. 2000 Dec;34(6):355-9. doi: 10.1054/npep.2000.0819. PMID: 11162292. 6: Schelfhout V, Van De Velde V, Maggi C, Pauwels R, Joos G. The effect of the tachykinin NK(2) receptor antagonist MEN11420 (nepadutant) on neurokinin A-induced bronchoconstriction in asthmatics. Ther Adv Respir Dis. 2009 Oct;3(5):219-26. doi: 10.1177/1753465809349741. PMID: 19880429. 7: Giuliani S, Guelfi M, Toulouse M, Buéno L, Lecci A, Tramontana M, Criscuoli M, Maggi CA. Effect of a tachykinin NK(2) receptor antagonist, nepadutant, on cardiovascular and gastrointestinal function in rats and dogs. Eur J Pharmacol. 2001 Mar 9;415(1):61-71. doi: 10.1016/s0014-2999(01)00794-4. PMID: 11245853. 8: Tramontana M, Evangelista S, Giuliani S, Manzini S, Robelet S, Girod V, Maggi CA. Influence of tachykinin NK2 receptors on intestinal sensitivity and motility in newborn rats. Neuropeptides. 2010 Jun;44(3):269-72. doi: 10.1016/j.npep.2010.01.002. PMID: 20137809. 9: Lecci A, Capriati A, Altamura M, Maggi CA. Tachykinins and tachykinin receptors in the gut, with special reference to NK2 receptors in human. Auton Neurosci. 2006 Jun 30;126-127:232-49. doi: 10.1016/j.autneu.2006.02.014. Epub 2006 Apr 17. PMID: 16616700. 10: Tramontana M, Santicioli P, Giuliani S, Catalioto RM, Lecci A, Carini F, Maggi CA. Role of tachykinins in sephadex-induced airway hyperreactivity and inflammation in guinea pigs. Eur J Pharmacol. 2002 Mar 29;439(1-3):149-58. doi: 10.1016/s0014-2999(02)01365-1. PMID: 11937105.