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Details

Stereochemistry ACHIRAL
Molecular Formula C17H20N4O
Molecular Weight 296.3669
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VAPITADINE

SMILES

NC(=O)C1=CN=C2N1CCC3=C(C=CC=C3)C24CCNCC4

InChI

InChIKey=VQWGYPVNVICKFC-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C17H20N4O
Molecular Weight 296.3669
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Vapitadine (R129160; Hivenyl™) 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. Vapitadine is a new selective, non-sedative H1antihistamine. In several in vitro and in vivo pharmacological models, vapitadine is at least as potent as cetirizine (Zyrtec®) and does not penetrate the blood-brain barrier. An advantage of vapitadine over other antihistamines may be the absence of the sedation, even at high doses. Vapitadine had been in phase II clinical trials for the treatment of patients with atopic dermatitis. However, no development has been reported.

Originator

Curator's Comment: Vapitadine was originally discovered by Johnson&Johnson, then licensed to Stiefel Laboratories (acquired by GlaxoSmithKline in 2009).

Approval Year

PubMed

PubMed

TitleDatePubMed
Norpiperidine imidazoazepines as a new class of potent, selective, and nonsedative H1 antihistamines.
2005 Mar 24
Patents

Sample Use Guides

In healthy volunteers vapitadine dose-dependently inhibits the histamine-induced wheal and flare reaction. Vapitadine shows a fast onset of action (within 1 hour) as well as a long-lasting (>24 hours) antihistaminic activity (from 10 mg onwards). Vapitadine does not induce sedation up to the highest dose tested (150 mg o.d. for 8 days). After a one-week run-in period, 43 adult patients with atopic dermatitis were randomized to treatment with oral vapitadine 60 mg twice daily (n=22) or placebo (n=21) for one week.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:31 GMT 2023
Edited
by admin
on Fri Dec 15 16:04:31 GMT 2023
Record UNII
Z5014VUX83
Record Status Validated (UNII)
Record Version
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Name Type Language
VAPITADINE
INN   WHO-DD  
INN  
Official Name English
vapitadine [INN]
Common Name English
SPIRO(11H-IMIDAZO(2,1-B)(3)BENZAZEPINE-11,4'-PIPERIDINE)-2-CARBOXAMIDE, 5,6-DIHYDRO-
Systematic Name English
Vapitadine [WHO-DD]
Common Name English
5,6-DIHYDROSPIRO(IMIDAZO(2,1-B)(3)BENZAZEPINE-11,4'-PIPERIDINE)-2-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C96721
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
PUBCHEM
9842252
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL369075
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
CAS
793655-64-8
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
DRUG BANK
DB05738
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
INN
8768
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
SMS_ID
300000037031
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID40229632
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
FDA UNII
Z5014VUX83
Created by admin on Fri Dec 15 16:04:31 GMT 2023 , Edited by admin on Fri Dec 15 16:04:31 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY