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Netupitant

CAT: 0804-HY-16346-05Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-16346-05Size:100 mg
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Description
Netupitant (CID-6451149) is a highly potent, selective and orally active neurokinin-1 (NK1) receptor antagonist with a Ki of 0.95 nM for hNK1 in CHO cells. Netupitant has antiemetic affect[1][2][3].
CAS Number
290297-26-6
Product Name Alternative
CID 6451149
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Neurokinin Receptor
Type
Reference compound
Related Pathways
GPCR/G Protein; Neuronal Signaling
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease; Endocrinology; Cancer
Assay Protocol
https://www.medchemexpress.com/Netupitant.html
Concentration
10mM
Purity
99.90
Solubility
DMSO : 9.09 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
CN1CCN(C2=CC(C3=C(C)C=CC=C3)=C(N(C)C(C(C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)(C)C)=O)C=N2)CC1
Molecular Formula
C30H32F6N4O
Molecular Weight
578.59
Precautions
H302, H315, H319, H335
References & Citations
[1]Hoffmann T, et al. Design and synthesis of a novel, achiral class of highly potent and selective, orally active neurokinin-1 receptor antagonists. Bioorg Med Chem Lett. 2006 Mar 1;16 (5) :1362-5.|[2]Rizzi A, et al. In vitro and in vivo pharmacological characterization of the novel NK1 receptor selective antagonist Netupitant. Peptides. 2012 Sep;37 (1) :86-97.|[3]Stefano Palea, et al. 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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Netupitant

Netupitant is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoic acid with the secondary amino group of N-methyl-4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-amine; an antiemetic used in combination with palonosetron hydrochloride (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy. It has a role as an antiemetic and a neurokinin-1 receptor antagonist. It is a member of toluenes, a monocarboxylic acid amide, an organofluorine compound, an aminopyridine, a N-alkylpiperazine and a N-arylpiperazine.

CAS Number290297-26-6
PubChem CID6451149
IUPAC Name2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)-3-pyridinyl]propanamide
Molecular FormulaC30H32F6N4O
Molecular Weight578.6
XLogP6.8
Topological Polar Surface Area39.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Heavy Atom Count41
Formal Charge0
Complexity865
SMILES
CC1=CC=CC=C1C2=CC(=NC=C2N(C)C(=O)C(C)(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C
InChI
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
InChIKey
WAXQNWCZJDTGBU-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Netupitant
CAS: 290297-26-6
CID: 6451149
Formula: C30H32F6N4O
MW: 578.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight578.6
XLogP36.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Exact Mass578.24803063
Monoisotopic Mass578.24803063
Topological Polar Surface Area39.7 Ų
Heavy Atom Count41
Formal Charge0
Complexity865
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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