Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01467)
Name
Tecovirimat
Synonyms    Click to Show/Hide the Synonyms of This API
Tecovirimat; ST 246; SIGA-246; UNII-F925RR824R; ST-246; 869572-92-9; F925RR824R; TPOXX; 816458-31-8; Tecovirimat [USAN:INN]; SIGA 246; 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-; 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-; SCHEMBL404743; CHEMBL1257073; SCHEMBL21670085; EX-A4340; ZINC35323125; AKOS030260536; CS-3464; DB12020; HY-14805; N-(dioxo[?]yl)-4-(trifluoromethyl)benzamide; 458T318; Q7692792; 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; N-[(3aR,4R,4aR,5aS,6S,6aS)-1,3-Dioxooctahydro-4,6-ethenocyclopropa[f]isoindol-2(1H)-yl]-4-(trifluoromethyl)benzamide
Clinical Status
Approved
PubChem CID
16124688
Formula
C19H15F3N2O3
Canonical SMILES
C1[C@@H]2[C@H]1[C@@H]3C=C[C@H]2[C@@H]4[C@H]3C(=O)N(C4=O)NC(=O)C5=CC=C(C=C5)C(F)(F)F
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+
InChIKey
CSKDFZIMJXRJGH-VWLPUNTISA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=16124688"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 376.3 Topological Polar Surface Area 66.5
XlogP 2.6 Complexity 705
Heavy Atom Count 27 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Tecovirimat 200 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Colloidal Silicon Dioxide; Croscarmellose Sodium; Hydroxypropyl Methyl Cellulose; Lactose Monohydrate; Magnesium Stearate; Microcrystalline Cellulose; Sodium Lauryl Sulfate; Gelatin; Fd&C Blue 1; Fd&C Red 3; Fd&C Yellow 6; Titanium Dioxide
                   Dosage Form Capsule
                   Company Siga Technologies
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [1]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [1]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [1]
Erythrosine sodium anhydrous DIG Info Multidrug resistance protein 3 (IC50 = 133000 nM) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [3]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
References
1 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
2 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov; 136(1):216-41.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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