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Chemistry

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Also known as: 869572-92-9, Siga-246, St 246, Tpoxx, St-246, F925rr824r

Molecular Formula

C₁₉H₁₅F₃N₂O₃

Molecular Weight

376.3 g/mol

InChI Key

CSKDFZIMJXRJGH-VWLPUNTISA-N

FDA UNII

F925RR824R

Tecovirimat is an orally available small molecule with activity against orthopoxviruses. Tecovirimat is an inhibitor of viral p37 and blocks the ability of virus particles to be released from infected cells.

Tecovirimat is an Orthopoxvirus VP37 Envelope Wrapping Protein Inhibitor. The mechanism of action of tecovirimat is as a Cytochrome P450 3A Inducer, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C19 Inhibitor, and Breast Cancer Resistance Protein Inhibitor.

1 2D Structure

Tecovirimat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(1S,2S,6R,7R,8R,10S)-3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl]-4-(trifluoromethyl)benzamide

2.1.2 InChI

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+

2.1.3 InChI Key

CSKDFZIMJXRJGH-VWLPUNTISA-N

2.1.4 Canonical SMILES

C1C2C1C3C=CC2C4C3C(=O)N(C4=O)NC(=O)C5=CC=C(C=C5)C(F)(F)F

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

F925RR824R

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-trifluoromethyl-n-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop(f)isoindol-2(1h)-yl)-benzamide

2. 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)-, Hydrate (1:1), Rel-

3. 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

4. Siga-246

5. St 246

6. St-246

7. Tecovirimat Monohydrate

8. Tpoxx

2.3.2 Depositor-Supplied Synonyms

1. 869572-92-9

2. Siga-246

3. St 246

4. Tpoxx

5. St-246

6. F925rr824r

7. 816458-31-8

8. N-(3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl)-4-(trifluoromethyl)benzamide

9. N-[(1r,2r,6s,7s,8s,10r)-3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl]-4-(trifluoromethyl)benzamide

10. 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-

11. Tecovirimat [usan]

12. Tecovirimat [usan:inn]

13. Unii-f925rr824r

14. Siga 246

15. 4-trifluoromethyl-n-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop(f)isoindol-2(1h)-yl)-benzamide

16. 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-

17. 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

18. Tecovirimat [mi]

19. Tecovirimat [inn]

20. Tecovirimat [who-dd]

21. Schembl404743

22. Arestvyr;iga-246;t-246

23. Chembl1257073

24. Schembl21670085

25. Tecovirimat [orange Book]

26. Dtxsid101026474

27. Ex-a4340

28. Bdbm50577060

29. S3380

30. St-246st-246

31. Zinc35323125

32. Akos030260536

33. Cs-3464

34. Db12020

35. Hy-14805

36. N-(dioxo[?]yl)-4-(trifluoromethyl)benzamide

37. 458t318

38. Q7692792

39. N-[(3ar,4r,4ar,5as,6s,6as)-1,3-dioxooctahydro-4,6-ethenocyclopropa[f]isoindol-2(1h)-yl]-4-(trifluoromethyl)benzamide

2.4 Create Date

2007-06-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₅F₃N₂O₃
Molecular Weight	376.3 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	376.10347683 g/mol
Monoisotopic Mass	376.10347683 g/mol
Topological Polar Surface Area	66.5 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	705
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Tecovirimat is an inhibitor of the orthopoxvirus VP37 envelope wrapping protein and is indicated for the treatment of human smallpox disease in adults and pediatric patients weighing at least 13 kg. The efficacy of tecovirimat may be reduced in immunocompromised patients.

FDA Label

Tecovirimat SIGA is indicated for the treatment of the following viral infections in adults and children with body weight at least 13 kg:

- Smallpox

- Monkeypox

- Cowpox

Tecovirimat SIGA is also indicated to treat complications due to replication of vaccinia virus following vaccination against smallpox in adults and children with body weight at least 13 kg (see sections 4. 4 and 5. 1).

Tecovirimat SIGA should be used in accordance with official recommendations.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tecovirimat prevents viral spread throughout the body. This drug inhibits its molecular target, a protein called p37, from interacting with intracellular transport components necessary for the production of enveloped virus, and therefore the spread of virus.

5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

TECOVIRIMAT

5.3.2 FDA UNII

F925RR824R

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors

5.4 ATC Code

J05AX24

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AX - Other antivirals

J05AX24 - Tecovirimat

5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed following oral administration, with mean times to maximum concentration from 3 to 4 h. A study was conducted to determine the safety, tolerability, and pharmacokinetics of ST-246 administered as a single daily oral dose. Steady state was reached by day 6 (within 3 to 5 half-lives).

Route of Elimination

Less than 0.02% of the drug is excreted unchanged in the kidney, with a majority of the drug being excreted in glucuronidated form. Approximately 23% of unchanged drug is found in the feces.

Volume of Distribution

Approximately 1,356 L. Following oral administration in mice, [14C]-tecovirimat was distributed to all tissues analyzed with the highest concentrations noted in liver and gallbladder, respiratory tract tissues (i.e., nasal turbinates), and bone marrow. Studies in dogs and NHPs suggest that tecovirimat crosses the blood-brain barrier.

Clearance

Mainly renal.

5.6 Metabolism/Metabolites

In vitro studies indicate that tecovirimat is not a substrate of major cytochrome P450 (CYP) enzymes, but it is a substrate of human recombinant UGTs (specifically of UGT1A1 and 1A4). Tecovirimat was found to be metabolized into 3 most abundant metabolites, M4, M5 and TFMBA, which do not have pharmacological activity.

5.7 Biological Half-Life

Approximately 20h.

5.8 Mechanism of Action

Tecovirimat inhibits the production of extracellular viral forms, which are responsible for the systemic spread of infection, inhibiting virus-induced cytopathic effects. Tecovirimat does not inhibit the formation of intracellular forms of the virus (IMV); however, by inhibiting envelopment, and therefore preventing the exit of viral particles from an infected cell, the smallpox infection is slowed to a point where the immune system can eliminate the virus. Tecovirimat has shown a high level of selectivity and specificity for orthopoxviruses. Tecovirimat targets the viral p37 protein, a highly conserved protein with no homologs outside of the Orthopoxvirus genus, inhibiting its function that is necessary for required for the viral envelopment of IMV (intracellular mature virus). Tecovirimat interferes with the cellular localization of p37 viral protein and prevents its association with cellular proteins involved in membrane trafficking.

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