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Details

Stereochemistry ACHIRAL
Molecular Formula C19H15F3N2O3
Molecular Weight 376.3292
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TECOVIRIMAT

SMILES

FC(F)(F)C1=CC=C(C=C1)C(=O)NN2C(=O)[C@H]3[C@H]([C@H]4C=C[C@@H]3[C@@H]5C[C@H]45)C2=O

InChI

InChIKey=CSKDFZIMJXRJGH-VWLPUNTISA-N
InChI=1S/C19H15F3N2O3/c20-19(21,22)9-3-1-8(2-4-9)16(25)23-24-17(26)14-10-5-6-11(13-7-12(10)13)15(14)18(24)27/h1-6,10-15H,7H2,(H,23,25)/t10-,11+,12+,13-,14-,15+

HIDE SMILES / InChI

Description

Tecovirimat (ST-246) is a low-molecular-weight compound (molecular weight = 376), that is potent (concentration that inhibited virus replication by 50% = 0.010 microM), selective (concentration of compound that inhibited cell viability by 50% = >40 microM), and active against multiple orthopoxviruses, including vaccinia, monkeypox, camelpox, cowpox, ectromelia (mousepox), and variola viruses. The antiviral activity is specific for orthopoxviruses and the compound does not inhibit the replication of other RNA- and DNA-containing viruses or inhibit cell proliferation at concentrations of compound that are antiviral. ST-246 targets vaccinia virus p37, a viral protein required for envelopment and secretion of extracellular forms of virus. The compound is orally bioavailable and protects multiple animal species from lethal orthopoxvirus challenge. rug substance and drug product processes have been developed and commercial scale batches have been produced using Good Manufacturing Processes (GMP). Human phase I clinical trials have shown that ST-246 is safe and well tolerated in healthy human volunteers. Based on the results of the clinical evaluation, once a day dosing should provide plasma drug exposure in the range predicted to be antiviral based on data from efficacy studies in animal models of orthopoxvirus disease.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
PMID

PMID

TitleDatePMID
An orally bioavailable antipoxvirus compound (ST-246) inhibits extracellular virus formation and protects mice from lethal orthopoxvirus Challenge.
2005 Oct
Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents.
2010 Sep
Patent

Sample Use Guides

In Vivo Use Guide
Phase 2, double-blind, randomized, placebo-controlled, multicenter trial was conducted to assess the safety, tolerability, and pharmacokinetics (PK) of tecovirimat (ST-246) when administered as a single daily oral dose (400 mg or 600 mg) for 14 days in fed adult volunteers.
Route of Administration: Oral
In Vitro Use Guide
BSC-40 cells were infected with 2 PFU/cell of vaccinia virus and incubated in the presence and absence of 5 uM tecovirimat (ST-246) . At selected times postinfection, extracellular virus in the medium and cell associated virus were quantified by plaque assay. The results show that ST-246 reduced extracellular virus titers by approximately 10 fold at 24 h postinfection, while having little effect on the level of intracellular virus titers relative to untreated controls. These results suggest that ST-246 inhibits extracellular virus formation.
Name Type Language
TECOVIRIMAT
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
TECOVIRIMAT [INN]
Common Name English
TECOVIRIMAT [USAN]
Common Name English
BENZAMIDE, N-((3AR,4R,4AR,5AS,6S,6AS)-3,3A,4,4A,5,5A,6,6A-OCTAHYDRO-1,3-DIOXO-4,6-ETHENOCYCLOPROP(F)ISOINDOL-2(1H)-YL)-4-(TRIFLUOROMETHYL)-, REL-
Common Name English
TECOVIRIMAT [MI]
Common Name English
SIGA-246
Code English
ST-246
Code English
TECOVIRIMAT [WHO-DD]
Common Name English
ST 246
Code English
N-((3AR,4R,4AR,5AS,6S,6AS)-1,3-DIOXO-3,3A,4,4A,5,5A,6,6A-OCTAHYDRO-4,6-ETHENOCYCLOPROPA(F)ISOINDOL-2(1H)-YL)-4-(TRIFLUOROMETHYL)BENZAMIDE
Common Name English
Code System Code Type Description
MESH
C505045
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY
ChEMBL
CHEMBL1242629
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY
INN
9011
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY
WIKIPEDIA
TECOVIRIMAT
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY
CAS
869572-92-9
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY
MERCK INDEX
M10514
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY Merck Index
PUBCHEM
16124688
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C81606
Created by admin on Tue Mar 06 16:18:51 UTC 2018 , Edited by admin on Tue Mar 06 16:18:51 UTC 2018
PRIMARY