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MedKoo Cat#: 205981 | Name: Netupitant
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Description:

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

Netupitant is a selective antagonist of the neurokinin-1 (NK1) receptor, which binds the endogenous ligand substance P. In vitro studies have shown that netupitant exhibits high affinity for human NK1 receptors, with a Ki value of approximately 0.96 nM in radioligand binding assays. Functional assays in CHO cells expressing human NK1 receptors demonstrated that netupitant effectively inhibits substance P–induced intracellular calcium mobilization, with an IC₅₀ around 8.4 nM. Importantly, netupitant displays over 1,000-fold selectivity over NK2 and NK3 receptors, indicating strong receptor subtype specificity.

Chemical Structure

Netupitant
Netupitant
CAS#290297-26-6 (free base)

Theoretical Analysis

MedKoo Cat#: 205981

Name: Netupitant

CAS#: 290297-26-6 (free base)

Chemical Formula: C30H32F6N4O

Exact Mass: 578.2480

Molecular Weight: 578.59

Elemental Analysis: C, 62.28; H, 5.57; F, 19.70; N, 9.68; O, 2.77

Price and Availability

Size Price Availability Quantity
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 425.00 Ready to ship
200mg USD 685.00 Ready to ship
500mg USD 1,150.00 Ready to ship
1g USD 1,950.00 Ready to ship
2g USD 2,850.00 Ready to ship
5g USD 4,650.00 Ready to ship
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Related CAS #
290297-26-6 (free base)
Synonym
AGE94200; AGE-94200; AGE 94200;Ro 67-3189; Ro-67-3189; Ro67-3189; Ro 67-3189/000; Netupitant.
IUPAC/Chemical Name
2-(3,5-bis(trifluoromethyl)phenyl)-N,2-dimethyl-N-(6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)propanamide
InChi Key
WAXQNWCZJDTGBU-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H32F6N4O/c1-19-8-6-7-9-23(19)24-17-26(40-12-10-38(4)11-13-40)37-18-25(24)39(5)27(41)28(2,3)20-14-21(29(31,32)33)16-22(15-20)30(34,35)36/h6-9,14-18H,10-13H2,1-5H3
SMILES Code
CC(C)(C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)C(N(C)C2=C(C3=CC=CC=C3C)C=C(N4CCN(C)CC4)N=C2)=O
Appearance
White 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
  The NK-receptor is a G-protein receptor coupled to the inositol phosphate signal-transduction pathway and is found in both the nucleus tractus solitarii and the area postrema.      
Biological target:
Netupitant (CID-6451149) is a neurokinin-1 (NK1) receptor antagonist with a Ki of 0.95 nM for hNK1 in CHO cells.
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 2.0 3.50
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 578.59 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
Formulation protocol:
1. Rudd JA, Ngan MP, Lu Z, Higgins GA, Giuliano C, Lovati E, Pietra C. Profile of Antiemetic Activity of Netupitant Alone or in Combination with Palonosetron and Dexamethasone in Ferrets and Suncus murinus (House Musk Shrew). Front Pharmacol. 2016 Aug 31;7:263. doi: 10.3389/fphar.2016.00263. PMID: 27630563; PMCID: PMC5005416. 2. Palea S, Guilloteau V, Rekik M, Lovati E, Guerard M, Guardia MA, Lluel P, Pietra C, Yoshiyama M. Netupitant, a Potent and Highly Selective NK1 Receptor Antagonist, Alleviates Acetic Acid-Induced Bladder Overactivity in Anesthetized Guinea-Pigs. Front Pharmacol. 2016 Aug 4;7:234. doi: 10.3389/fphar.2016.00234. PMID: 27540361; PMCID: PMC4972833.
In vitro protocol:
TBD
In vivo protocol:
1. Rudd JA, Ngan MP, Lu Z, Higgins GA, Giuliano C, Lovati E, Pietra C. Profile of Antiemetic Activity of Netupitant Alone or in Combination with Palonosetron and Dexamethasone in Ferrets and Suncus murinus (House Musk Shrew). Front Pharmacol. 2016 Aug 31;7:263. doi: 10.3389/fphar.2016.00263. PMID: 27630563; PMCID: PMC5005416. 2. Palea S, Guilloteau V, Rekik M, Lovati E, Guerard M, Guardia MA, Lluel P, Pietra C, Yoshiyama M. Netupitant, a Potent and Highly Selective NK1 Receptor Antagonist, Alleviates Acetic Acid-Induced Bladder Overactivity in Anesthetized Guinea-Pigs. Front Pharmacol. 2016 Aug 4;7:234. doi: 10.3389/fphar.2016.00234. PMID: 27540361; PMCID: PMC4972833.
1: Lorusso V, Karthaus M, Aapro M. Review of oral fixed-dose combination netupitant and palonosetron (NEPA) for the treatment of chemotherapy-induced nausea and vomiting. Future Oncol. 2014 Oct 31:1-13. [Epub ahead of print] PubMed PMID: 25360998. 2: Spinelli T, Moresino C, Baumann S, Timmer W, Schultz A. Effects of combined netupitant and palonosetron (NEPA), a cancer supportive care antiemetic, on the ECG of healthy subjects: an ICH E14 thorough QT trial. Springerplus. 2014 Jul 29;3:389. doi: 10.1186/2193-1801-3-389. eCollection 2014. PubMed PMID: 25105088; PubMed Central PMCID: PMC4124105. 3: Thomas AG, Stathis M, Rojas C, Slusher BS. Netupitant and palonosetron trigger NK1 receptor internalization in NG108-15 cells. Exp Brain Res. 2014 Aug;232(8):2637-44. doi: 10.1007/s00221-014-4017-7. Epub 2014 Jun 27. PubMed PMID: 24969614; PubMed Central PMCID: PMC4112047. 4: Andrews PL. Netupitant and palonosetron (NEPA): a winning team in the race for the optimal treatment of chemotherapy-induced nausea and vomiting? Ann Oncol. 2014 Jul;25(7):1258-9. doi: 10.1093/annonc/mdu190. Epub 2014 Jun 18. PubMed PMID: 24942276. 5: Gralla RJ, Bosnjak SM, Hontsa A, Balser C, Rizzi G, Rossi G, Borroni ME, Jordan K. A phase III study evaluating the safety and efficacy of NEPA, a fixed-dose combination of netupitant and palonosetron, for prevention of chemotherapy-induced nausea and vomiting over repeated cycles of chemotherapy. Ann Oncol. 2014 Jul;25(7):1333-9. doi: 10.1093/annonc/mdu096. Epub 2014 Mar 14. PubMed PMID: 24631949; PubMed Central PMCID: PMC4071753. 6: Hesketh PJ, Rossi G, Rizzi G, Palmas M, Alyasova A, Bondarenko I, Lisyanskaya A, Gralla RJ. Efficacy and safety of NEPA, an oral combination of netupitant and palonosetron, for prevention of chemotherapy-induced nausea and vomiting following highly emetogenic chemotherapy: a randomized dose-ranging pivotal study. Ann Oncol. 2014 Jul;25(7):1340-6. doi: 10.1093/annonc/mdu110. Epub 2014 Mar 7. PubMed PMID: 24608196; PubMed Central PMCID: PMC4071755. 7: Aapro M, Rugo H, Rossi G, Rizzi G, Borroni ME, Bondarenko I, Sarosiek T, Oprean C, Cardona-Huerta S, Lorusso V, Karthaus M, Schwartzberg L, Grunberg S. A randomized phase III study evaluating the efficacy and safety of NEPA, a fixed-dose combination of netupitant and palonosetron, for prevention of chemotherapy-induced nausea and vomiting following moderately emetogenic chemotherapy. Ann Oncol. 2014 Jul;25(7):1328-33. doi: 10.1093/annonc/mdu101. Epub 2014 Mar 5. PubMed PMID: 24603643; PubMed Central PMCID: PMC4071754. 8: Szitter I, Pintér E, Perkecz A, Kemény A, Kun J, Kereskai L, Pietra C, Quinn JP, Zimmer A, Berger A, Paige CJ, Helyes Z. Role of neurokinin 1 receptors in dextran sulfate-induced colitis: studies with gene-deleted mice and the selective receptor antagonist netupitant. Inflamm Res. 2014 May;63(5):399-409. doi: 10.1007/s00011-014-0712-x. Epub 2014 Jan 28. PubMed PMID: 24468892. 9: Spinelli T, Calcagnile S, Giuliano C, Rossi G, Lanzarotti C, Mair S, Stevens L, Nisbet I. Netupitant PET imaging and ADME studies in humans. J Clin Pharmacol. 2014 Jan;54(1):97-108. doi: 10.1002/jcph.198. Epub 2013 Nov 8. PubMed PMID: 24122871. 10: Haab F, Braticevici B, Krivoborodov G, Palmas M, Zufferli Russo M, Pietra C. Efficacy and safety of repeated dosing of netupitant, a neurokinin-1 receptor antagonist, in treating overactive bladder. Neurourol Urodyn. 2014 Mar;33(3):335-40. doi: 10.1002/nau.22406. Epub 2013 Jun 14. PubMed PMID: 23765630.