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Details

Stereochemistry ACHIRAL
Molecular Formula C21H26N4O3.2H3O4P
Molecular Weight 578.4465
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Vapendavir diphosphate

SMILES

OP(O)(O)=O.OP(O)(O)=O.CCOC1=NOC2=C1C=CC(OCCC3CCN(CC3)C4=NN=C(C)C=C4)=C2

InChI

InChIKey=MIUFDXZDQWMWRR-UHFFFAOYSA-N
InChI=1S/C21H26N4O3.2H3O4P/c1-3-26-21-18-6-5-17(14-19(18)28-24-21)27-13-10-16-8-11-25(12-9-16)20-7-4-15(2)22-23-20;2*1-5(2,3)4/h4-7,14,16H,3,8-13H2,1-2H3;2*(H3,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula H3O4P
Molecular Weight 97.9952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H26N4O3
Molecular Weight 382.4561
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Vapendavir (BTA-798) is an orally active capsid-binding inhibitor. It is a potent, orally bioavailable, broad spectrum inhibitor of the large group of HRVs. Vapendavir binds tightly to VP1s canyon and disrupts the ability of the capsid to bind to a specific cell surface receptor. This further inhibits the release of the viral RNA into the cell cytoplasm during the viral uncoating process (removing the lipid bilayer), thereby disrupting viral replication. Vapendavir is designed to be dosed orally. Vapendavir is in phase II clinical trials for the treatment of rhinovirus-induced aggravation of pre-existing asthma or COPD. Vapendavir has shown significant results in proof-of-concept studies. Thus far, from the Phase 1/2 studies conducted, vapendavir has demonstrated a desirable clinical pharmacology profile with high bioavailability, linear pharmacokinetic profile, remained unaffected by concomitant medications, and was not exclusively metabolized.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antiviral Activity of Broad-Spectrum and Enterovirus-Specific Inhibitors against Clinical Isolates of Enterovirus D68.
2015-12
The capsid binder Vapendavir and the novel protease inhibitor SG85 inhibit enterovirus 71 replication.
2014-11
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: 300-patient, multicenter, randomized, double-blind, placebo-controlled study of vapendavir in adults with mild to moderate asthma who also had symptoms of HRV infection. The purpose of the study was to evaluate the safety, tolerability and effectiveness of vapendavir in reducing the duration and symptoms of common cold, asthma, and lowering the risk of asthma exacerbation. Roughly 1200 individuals were screened in order to randomize 300 subjects, 155 in the vapendavir arm and 145 in the placebo group.Vapendavir was given two times daily for six consecutive days. Subjects who received 264 mg of vapendavir showed significant reduction in mean viral load. http://s1.q4cdn.com/460208960/files/Feb-8-2016_BOTA_Dushyanth.pdf
Rhinovirus, Upper Respiratory Tract Infection: Vapendavir Tablets, 264 mg, twice daily
Route of Administration: Oral
Vapendavir inhibited EV71 replication of all isolates (average EC50s of 0.7uM)
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:10:36 GMT 2025
Edited
by admin
on Mon Mar 31 21:10:36 GMT 2025
Record UNII
HLB8GQZ6FB
Record Status Validated (UNII)
Record Version
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Name Type Language
Vapendavir diphosphate
Common Name English
1,2-Benzisoxazole, 3-ethoxy-6-[2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy]-, phosphate (1:2)
Preferred Name English
3-ethoxy-6-[2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy]-1,2-benzisoxazole diphosphate
Systematic Name English
Code System Code Type Description
FDA UNII
HLB8GQZ6FB
Created by admin on Mon Mar 31 21:10:36 GMT 2025 , Edited by admin on Mon Mar 31 21:10:36 GMT 2025
PRIMARY
CAS
1198151-75-5
Created by admin on Mon Mar 31 21:10:36 GMT 2025 , Edited by admin on Mon Mar 31 21:10:36 GMT 2025
PRIMARY
PUBCHEM
44474071
Created by admin on Mon Mar 31 21:10:36 GMT 2025 , Edited by admin on Mon Mar 31 21:10:36 GMT 2025
PRIMARY
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