NAV

Casopitant

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Casopitant
DrugBank Accession Number
DB06634
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 616.625
Monoisotopic: 616.264823524
Chemical Formula
C30H35F7N4O2
Synonyms
  • Casopitant
External IDs
  • 679769
  • GW-679769
  • GW679769
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Pharmacology

Indication

Investigated for use/treatment in urinary incontinence and adverse effects (chemotherapy).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCytochrome P450 3A4Not AvailableHumans
UNeurokinin 1 receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Casopitant mesylate7VSV9BL497414910-30-8YRFKYVWDPCOSTE-REWBLLDVSA-N
International/Other Brands
Rezonic / Zunrisa

Categories

ATC Codes
A04AD13 — Casopitant
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Trifluoromethylbenzenes / Piperidinecarboxamides / Aminopiperidines / Aralkylamines / Toluenes / Fluorobenzenes / N-alkylpiperazines / Aryl fluorides / Tertiary carboxylic acid amides / Acetamides
show 10 more
Substituents
1,4-diazinane / 1-piperidinecarboxamide / 4-aminopiperidine / Acetamide / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound
show 29 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
3B03KPM27L
CAS number
414910-27-3
InChI Key
XGGTZCKQRWXCHW-WMTVXVAQSA-N
InChI
InChI=1S/C30H35F7N4O2/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/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3/t19-,25+,27-/m1/s1
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
SMILES
C[C@@H](N(C)C(=O)N1CC[C@@H](C[C@@H]1C1=CC=C(F)C=C1C)N1CCN(CC1)C(C)=O)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F

References

General References
Not Available
ChemSpider
8092668
BindingDB
50336575
ChEBI
135967
ChEMBL
CHEMBL1672054
ZINC
ZINC000042856596
PharmGKB
PA166129533
Wikipedia
Casopitant

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedPreventionChemotherapy-Induced Nausea and Vomiting1
3CompletedPreventionPost Operative Nausea and Vomiting (PONV)2
3CompletedSupportive CareChemotherapy-Induced Nausea and Vomiting1
3CompletedTreatmentChemotherapy-Induced Nausea and Vomiting / Nausea / Vomiting1
3WithdrawnSupportive CareCancer / Cancer (Solid Tumors) / Chemotherapy-Induced Nausea and Vomiting / Nausea and vomiting1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00445 mg/mLALOGPS
logP4.73ALOGPS
logP4.97Chemaxon
logS-5.1ALOGPS
pKa (Strongest Basic)7.31Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area47.1 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity149.02 m3·mol-1Chemaxon
Polarizability57.87 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0004119000-37deea87c377cb794b0f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ba-0166197000-56b5a066871692e4ced3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0040092000-49f2241e871735ee5126
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0v4i-0022092000-be8f3c53d9f090ace782
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0266591000-ef07f5d9c1dbe4ec4174
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0023091000-cb01368a57cff71e06af
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-228.80174
predicted
DeepCCS 1.0 (2019)
[M+H]+230.86119
predicted
DeepCCS 1.0 (2019)
[M+Na]+236.72289
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Motta P, Pons N, Pagliarusco S, Pellegatti M, Bonomo F: Casopitant: in vitro data and SimCyp simulation to predict in vivo metabolic interactions involving cytochrome P450 3A4. Drug Metab Dispos. 2011 Mar;39(3):363-72. doi: 10.1124/dmd.110.035071. Epub 2010 Dec 13. [Article]
Details2. Neurokinin 1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tachykinin receptor activity
Specific Function
This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of aff...
Gene Name
TACR1
Uniprot ID
P25103
Uniprot Name
Substance-P receptor
Molecular Weight
46250.5 Da
References
  1. Di Fabio R, Alvaro G, Griffante C, Pizzi DA, Donati D, Mattioli M, Cimarosti Z, Guercio G, Marchioro C, Provera S, Zonzini L, Montanari D, Melotto S, Gerrard PA, Trist DG, Ratti E, Corsi M: Discovery and biological characterization of (2R,4S)-1'-acetyl-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2- methylphenyl)-N-methyl-4,4'-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate. J Med Chem. 2011 Feb 24;54(4):1071-9. doi: 10.1021/jm1013264. Epub 2011 Jan 13. [Article]

Drug created at March 19, 2008 16:42 / Updated at February 21, 2021 18:52