NAV

Vapitadine

Identification

Generic Name
Vapitadine
DrugBank Accession Number
DB05738
Background

Vapitadine is an antihistamine that Barrier Therapeutics is developing as a treatment for allergic reactions of the skin, such as those associated with hives and for the itch associated with atopic dermatitis. An advantage of vapitadine over other antihistamines may be the absence of the sedation, even at high doses.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 296.374
Monoisotopic: 296.16371128
Chemical Formula
C17H20N4O
Synonyms
  • Vapitadina
  • Vapitadine
  • Vapitadinum
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Pharmacology

Indication

Investigated for use/treatment in atopic dermatitis.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
Not Available

Interactions

Drug Interactions
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
Vapitadine dihydrochlorideR612XR8A9F279253-83-7BOYLPLUVCXUHDJ-UHFFFAOYSA-N
International/Other Brands
Hivenyl

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
2-heteroaryl carboxamides / Carbonylimidazoles / Azepines / Aralkylamines / Piperidines / N-substituted imidazoles / Benzenoids / Heteroaromatic compounds / Primary carboxylic acid amides / Amino acids and derivatives
show 5 more
Substituents
2-heteroaryl carboxamide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Azole / Benzazepine / Benzenoid
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Z5014VUX83
CAS number
793655-64-8
InChI Key
VQWGYPVNVICKFC-UHFFFAOYSA-N
InChI
InChI=1S/C17H20N4O/c18-15(22)14-11-20-16-17(6-8-19-9-7-17)13-4-2-1-3-12(13)5-10-21(14)16/h1-4,11,19H,5-10H2,(H2,18,22)
IUPAC Name
4',7'-diazaspiro[piperidine-4,2'-tricyclo[8.4.0.0^{3,7}]tetradecane]-1'(10'),3',5',11',13'-pentaene-6'-carboxamide
SMILES
NC(=O)C1=CN=C2N1CCC1=C(C=CC=C1)C21CCNCC1

References

General References
Not Available
PubChem Compound
9842252
PubChem Substance
175427029
ChemSpider
8017967
BindingDB
50163629
ChEMBL
CHEMBL369075
ZINC
ZINC000000008768

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.178 mg/mLALOGPS
logP1ALOGPS
logP0.81Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.89Chemaxon
pKa (Strongest Basic)9.96Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area72.94 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity96.14 m3·mol-1Chemaxon
Polarizability32.28 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8058
Caco-2 permeable-0.6131
P-glycoprotein substrateSubstrate0.7654
P-glycoprotein inhibitor INon-inhibitor0.6713
P-glycoprotein inhibitor IINon-inhibitor0.6579
Renal organic cation transporterInhibitor0.5687
CYP450 2C9 substrateNon-substrate0.7959
CYP450 2D6 substrateNon-substrate0.6874
CYP450 3A4 substrateSubstrate0.5664
CYP450 1A2 substrateInhibitor0.6098
CYP450 2C9 inhibitorNon-inhibitor0.6508
CYP450 2D6 inhibitorNon-inhibitor0.5851
CYP450 2C19 inhibitorNon-inhibitor0.5221
CYP450 3A4 inhibitorInhibitor0.7768
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7952
Ames testNon AMES toxic0.5455
CarcinogenicityNon-carcinogens0.8709
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7157 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9789
hERG inhibition (predictor II)Inhibitor0.7857
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-0090000000-9f5db7a53d6185e1eae2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0090000000-b53615fbf4155f5de8d0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-0090000000-734a3b84877f610a832d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0090000000-d108a799720667acc9cb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pbc-3970000000-264952ab35a65a5db66c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9150000000-5c363d704b5ae3dc5a2a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.8350405
predicted
DarkChem Lite v0.1.0
[M-H]-158.06667
predicted
DeepCCS 1.0 (2019)
[M+H]+176.2522405
predicted
DarkChem Lite v0.1.0
[M+H]+160.4247
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.8752405
predicted
DarkChem Lite v0.1.0
[M+Na]+166.51784
predicted
DeepCCS 1.0 (2019)

Drug created at November 18, 2007 18:27 / Updated at February 21, 2021 18:51