Tecovirimat monohydrateProduct ingredient for Tecovirimat

Name
Tecovirimat monohydrate
Drug Entry
Tecovirimat

The World Health Organization declared smallpox, a contagious and sometimes fatal infectious disease, eradicated in 1980. However, there have been longstanding concerns that smallpox may be used as a bioweapon.2,5 Tecovirimat is an antiviral drug that was identified via a high-throughput screen in 2002.2 It is effective against all orthopoxviruses, including vaccinia, cowpox, ectromelia, rabbitpox, monkeypox, and Variola (smallpox) virus.1,4

Tecovirimat was approved by the FDA in July 2018 as the first drug ever approved to treat smallpox.6,5 Tecovirimat was later approved by Health Canada in December 2021,7 followed by the approval from the European Commission in January 2022.9 Other than smallpox, tecovirimat is also indicated to treat complications due to replication of the vaccinia virus following vaccination against smallpox, and to treat monkeypox and cowpox in adults and children.8 Tecovirimat is available as both oral and intravenous formulations.10

Accession Number
DBSALT002799
Structure
Synonyms
Not Available
UNII
SB96YO2BR8
CAS Number
1162664-19-8
Weight
Average: 394.35
Monoisotopic: 394.114041524
Chemical Formula
C19H17F3N2O4
InChI Key
QRHXYGPOQKLBJP-NPIFKJBVSA-N
InChI
InChI=1S/C19H15F3N2O3.H2O/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);1H2/t10-,11+,12+,13-,14-,15+;
IUPAC Name
N-[(1R,2R,6S,7S,8S,10R)-3,5-dioxo-4-azatetracyclo[5.3.2.0^{2,6}.0^{8,10}]dodec-11-en-4-yl]-4-(trifluoromethyl)benzamide hydrate
SMILES
O.FC(F)(F)C1=CC=C(C=C1)C(=O)NN1C(=O)[C@H]2[C@H]([C@H]3C=C[C@@H]2[C@@H]2C[C@H]32)C1=O
ChemSpider
34993961
Predicted Properties
PropertyValueSource
Water Solubility0.021 mg/mLALOGPS
logP2.03ALOGPS
logP2.07Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.15Chemaxon
pKa (Strongest Basic)-6.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area66.48 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity89.45 m3·mol-1Chemaxon
Polarizability33.92 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon