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SML2755

Sigma-Aldrich

Netupitant

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C30H32F6N4O
Número de CAS:
290297-26-6
Peso molecular:
578.59
Número MDL:
MFCD25976831
Código UNSPSC:
12352200
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to beige

solubilidad

DMSO: 2 mg/mL, clear

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

WAXQNWCZJDTGBU-UHFFFAOYSA-N

Acciones bioquímicas o fisiológicas

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 Ki = 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.).

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315,H319

Clasificaciones de peligro

Eye Irrit. 2 - Skin Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000391900
0000391899
0000391900
0000391899
0000253344

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Ying Wang et al.
Journal of pain research, 12, 2419-2426 (2019-08-27)
Purpose: Chronic pain is a major comorbidity of sickle cell disease (SCD). Acupuncture, a non-opioid and non-addictive therapy to treat pain, was found to reduce pain in the majority (80%) of SCD patients in an earlier retrospective review. We observed
Beatrice Girard et al.
Experimental neurology, 285(Pt B), 110-125 (2016-10-25)
The mechanisms underlying the postnatal maturation of micturition from a somatovesical to a vesicovesical reflex are not known but may involve neuropeptides in the lower urinary tract. A transgenic mouse model with chronic urothelial overexpression (OE) of NGF exhibited increased
John A Rudd et al.
Frontiers in pharmacology, 7, 263-263 (2016-09-16)
Chemotherapy-induced acute and delayed emesis involves the activation of multiple pathways, with 5-hydroxytryptamine (5-HT; serotonin) playing a major role in the initial response. Substance P tachykinin NK1 receptor antagonists can reduce emesis induced by disparate emetic challenges and therefore have
Marigo Stathis et al.
European journal of pharmacology, 689(1-3), 25-30 (2012-06-12)
Netupitant is a potent and selective NK(1) receptor antagonist under development in combination with a fixed dose of palonosetron for the prevention of chemotherapy induced nausea and vomiting. Palonosetron is a 5-HT(3) receptor antagonist approved for both the prevention of
Torsten Hoffmann et al.
Bioorganic & medicinal chemistry letters, 16(5), 1362-1365 (2005-12-08)
The discovery of a novel, achiral pyridine class of potent and orally active neurokinin-1 (NK(1)) receptor antagonists is described. The evaluation of this class is briefly outlined, leading to the identification of netupitant 21 and befetupitant 29, two new proprietary
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