SML2755

Netupitant

≥98% (HPLC)

• Synonym(s): 2-(3,5-bis(Trifluoromethyl)phenyl)-N,2-dimethyl-N-(6-(4-methylpiperazin-1-yl)-4-o-tolylpyridin-3-yl)propanamide, 2-[3,5-bis(Trifluoromethyl)phenyl]-N-[6-(4-methylpiperazin-1-yl)-4-o-tolylpyridin-3-yl]-N-methylisobutyramide, AGE 94200, AGE-94200, AGE94200, CID 6451149, CID-6451149, CID6451149, N,a,a-Trimethyl-N-[4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl]-3,5-bis(trifluoromethyl)benzeneacetamide, Ro 67-31898, Ro 67-31898/000
• Empirical Formula (Hill Notation): C₃₀H₃₂F₆N₄O
• CAS Number: 290297-26-6
• Molecular Weight: 578.59
• MDL number: MFCD25976831
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: FC(F)(F)c1cc(cc(c1)C(C)(C)C(=O)N(C)c2cnc(cc2c4c(cccc4)C)N3CCN(CC3)C)C(F)(F)F
• 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
• InChI key: WAXQNWCZJDTGBU-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Brain-penetrant, orally active, potent and selective neurokinin-1 (NK1) receptor (NK1R; Tachykinin receptor 1) antagonist with antiemetic efficacy in vivo.

Netupitant is a brain-penetrant, orally active, potent and selective neurokinin-1 (NK1) receptor (NK1R; Tachykinin receptor 1) antagonist (Ca+2 mobilization IC₅₀ = 11.2 nM/hNK1 vs. >1 μM/rNK1 & hNK2/3; hNK1/2/3 K_i = 0.95 nM/1.6 μM/1.6 μM) that effectively blocks agonist GR73632-induced foot tapping in gerbils (ID₅₀ = 0.5 mg/kg po 2h prior to 3 pmol/5 μL GR73632/gerbil icv). In addition to antiemetic efficacy against substance P-associated vomiting reflexes, netupitant is also reported to enhance the analgesic effects of electroacupuncture (EA) among humanized mice with sickle cell disease in response to pain in vivo (10 mg/kg/day, i.p.).

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable