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Casopitant (mesylate)

CAT: 0804-HY-14405A-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-14405A-01Size:5 mg
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Description
Casopitant mesylate (GW679769B) is a potent, selective, brain permeable and orally active neurokinin 1 (NK1) receptor antagonist. Casopitant mesylate is a second in the class of antiemetics that acts to antagonise the emetogenic effect of Substance P. Casopitant mesylate is also a substrate and a weak-to-moderate inhibitor of CYP3A4. Casopitant mesylate can be used for chemotherapy-induced nausea and vomiting (CINV) and postoperative nausea and vomiting (PONV)[2].
CAS Number
414910-30-8
Product Name Alternative
GW679769B
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Cytochrome P450; Neurokinin Receptor
Type
Reference compound
Related Pathways
GPCR/G Protein; Metabolic Enzyme/Protease; Neuronal Signaling
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease; Cancer
Assay Protocol
https://www.medchemexpress.com/casopitant-mesylate.html
Purity
99.83
Solubility
DMSO : 33.33 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C(N1[C@@H](C2=CC=C(F)C=C2C)C[C@@H](N3CCN(C(C)=O)CC3)CC1)N([C@@H](C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)C)C.CS(=O)(O)=O
Molecular Formula
C31H39F7N4O5S
Molecular Weight
712.72
Precautions
H302, H315, H319, H335
References & Citations
[1]Ruhlmann C, et al. Casopitant: a novel NK (1) -receptor antagonist in the prevention of chemotherapy-induced nausea and vomiting. Ther Clin Risk Manag. 2009 Apr;5 (2) :375-84.|[2]Minthorn E, et al. Pharmacokinetics and brain penetration of casopitant, a potent and selective neurokinin-1 receptor antagonist, in the ferret. Drug Metab Dispos. 2008 Sep;36 (9) :1846-52.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Phase 3
Isoform
CYP3; NK1R

Chemical Information

Casopitant Mesylate

Casopitant Mesylate is the mesylate salt of a centrally-acting neurokinin 1 (NK1) receptor antagonist with antidepressant and antiemetic activities. Casopitant competitively binds to and blocks the activity of the NK-receptor, thereby inhibiting NK1-receptor binding of the endogenous tachykinin neuropeptide substance P (SP), which may result in antiemetic effects. SP is found in neurons of vagal afferent fibers innervating the brain-stem nucleus tractus solitarii and the area postrema, which contains the chemoreceptor trigger zone (CTZ), and may be elevated in response to chemotherapy. 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.

CAS Number414910-30-8
PubChem CID11686295
IUPAC Name(2R,4S)-4-(4-acetylpiperazin-1-yl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide;methanesulfonic acid
Molecular FormulaC31H39F7N4O5S
Molecular Weight712.7
Topological Polar Surface Area110
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count13
Rotatable Bond Count4
Heavy Atom Count48
Formal Charge0
Complexity1040
SMILES
CC1=C(C=CC(=C1)F)[C@H]2C[C@H](CCN2C(=O)N(C)[C@H](C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C(=O)C.CS(=O)(=O)O
InChI
InChI=1S/C30H35F7N4O2.CH4O3S/c1-18-13-24(31)5-6-26(18)27-17-25(40-11-9-39(10-12-40)20(3)42)7-8-41(27)28(43)38(4)19(2)21-14-22(29(32,33)34)16-23(15-21)30(35,36)37;1-5(2,3)4/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3;1H3,(H,2,3,4)/t19-,25+,27-;/m1./s1
InChIKey
YRFKYVWDPCOSTE-REWBLLDVSA-N
Chemical Structure
2D Structure
2D structure of Casopitant Mesylate
CAS: 414910-30-8
CID: 11686295
Formula: C31H39F7N4O5S
MW: 712.7
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight712.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count13
Rotatable Bond Count4
Exact Mass712.25293867
Monoisotopic Mass712.25293867
Topological Polar Surface Area110 Ų
Heavy Atom Count48
Formal Charge0
Complexity1040
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes