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Also known as: 1985606-14-1, Xofluza, Baloxavir-marboxil, Baloxavir marboxil [inn], S-033188, 505cxm6ohg

Molecular Formula

C₂₇H₂₃F₂N₃O₇S

Molecular Weight

571.6 g/mol

InChI Key

RZVPBGBYGMDSBG-GGAORHGYSA-N

FDA UNII

505CXM6OHG

Baloxavir Marboxil is an orally bioavailable prodrug and influenza cap-dependent endonuclease (CEN) inhibitor, with antiviral activity. Upon administration of baloxavir marboxil, the agent is converted by hydrolysis to its active metabolite baloxavir. Baloxavir targets, binds to and inhibits the CEN activity of the influenza polymerase acidic (PA) protein, an influenza virus-specific enzyme in the viral RNA polymerase complex required for the initiation of influenza gene transcription. By inhibiting PA endonuclease, influenza virus mRNA replication is halted. This reduces viral load and prevents further influenza infection.

1 2D Structure

Baloxavir Marboxil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(3R)-2-[(11S)-7,8-difluoro-6,11-dihydrobenzo[c][1]benzothiepin-11-yl]-9,12-dioxo-5-oxa-1,2,8-triazatricyclo[8.4.0.03,8]tetradeca-10,13-dien-11-yl]oxymethyl methyl carbonate

2.1.2 InChI

InChI=1S/C27H23F2N3O7S/c1-36-27(35)39-14-38-25-19(33)8-9-31-24(25)26(34)30-10-11-37-12-21(30)32(31)23-15-6-7-18(28)22(29)17(15)13-40-20-5-3-2-4-16(20)23/h2-9,21,23H,10-14H2,1H3/t21-,23+/m1/s1

2.1.3 InChI Key

RZVPBGBYGMDSBG-GGAORHGYSA-N

2.1.4 Canonical SMILES

COC(=O)OCOC1=C2C(=O)N3CCOCC3N(N2C=CC1=O)C4C5=C(CSC6=CC=CC=C46)C(=C(C=C5)F)F

2.1.5 Isomeric SMILES

COC(=O)OCOC1=C2C(=O)N3CCOC[C@H]3N(N2C=CC1=O)[C@H]4C5=C(CSC6=CC=CC=C46)C(=C(C=C5)F)F

2.2 Other Identifiers

2.2.1 UNII

505CXM6OHG

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (((12ar)-12-((11s)-7,8-difluoro-6,11-dihydrodibenzo(b,e)thiepin-11-yl)-6,8-dioxo-3,4,6,8,12,12ahexahydro-1h-(1,4)oxazino(3,4-c)pyrido(2,1-f)(1,2,4)triazin-7-yl)oxy)methyl Methyl Carbonate

2. (12ar)-12-((11s)-7,8-difluoro-6,11-dihydrodibenzo(b,e)thiepin-11-yl)-7-hydroxy-3,4,12,12a-tetrahydro-1h-(1,4)oxazino(3,4-c)pyrido(2,1-f)(1,2,4)triazine-6,8-dione

3. Baloxavir

4. Xofluza

2.3.2 Depositor-Supplied Synonyms

1. 1985606-14-1

2. Xofluza

3. Baloxavir-marboxil

4. Baloxavir Marboxil [inn]

5. S-033188

6. 505cxm6ohg

7. (((r)-12-((s)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-6,8-dioxo-3,4,6,8,12,12a-hexahydro-1h-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin-7-yl)oxy)methyl Methyl Carbonate

8. (((12ar)-12-((11s)-7,8-difluoro-6,11-dihydrodibenzo(b,e)thiepin-11-yl)-6,8-dioxo-3,4,6,8,12,12ahexahydro-1h-(1,4)oxazino(3,4-c)pyrido(2,1-f)(1,2,4)triazin-7-yl)oxy)methyl Methyl Carbonate

9. ({(12ar)-12-[(11s)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl]-6,8-dioxo-3,4,6,8,12,12ahexahydro-1h-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin-7-yl}oxy)methyl Methyl Carbonate

10. [(3r)-2-[(11s)-7,8-difluoro-6,11-dihydrobenzo[c][1]benzothiepin-11-yl]-9,12-dioxo-5-oxa-1,2,8-triazatricyclo[8.4.0.03,8]tetradeca-10,13-dien-11-yl]oxymethyl Methyl Carbonate

11. Carbonic Acid, (((12ar)-12-((11s)-7,8-difluoro-6,11-dihydrodibenzo(b,e)thiepin-11-yl)-3,4,6,8,12,12a-hexahydro-6,8-dioxo-1h-(1,4)oxazino(3,4-c)pyrido(2,1-f)(1,2,4)triazin-7-yl)oxy)methyl Methyl Ester

12. Xofluza (tn)

13. Unii-505cxm6ohg

14. Baloxavir Marboxil [mi]

15. Baloxavir Marboxil [jan]

16. Chembl4297503

17. Schembl20108731

18. Gtpl11748

19. Baloxavir Marboxil [usan]

20. Dtxsid601027758

21. Amy16544

22. Baloxavir Marboxil [who-dd]

23. Ex-a1867

24. Baloxavir Marboxil (jan/usan/inn)

25. S5952

26. Akos037652423

27. Db13997

28. Dt-0012

29. Baloxavir Marboxil [orange Book]

30. Ac-30675

31. Hy-109025

32. Cs-0030527

33. D11021

34. D70046

35. A937215

36. S033188

37. Q48333728

38. (((12ar)-12-((11s)-7,8-difluoro-6,11-dihydrodibenzo(b,e)thiepin-11-yl)-6,8-dioxo-3,4,6,8,12,12a-hexahydro-1h -(1,4)oxazino(3,4-c)pyrido(2,1-f)(1,2,4)triazin-7-yl)oxy)methyl Methylcarbonate

39. (((r)-12-((s)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-6,8-dioxo-3,4,6,8,12,12a-hexahydro-1h-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin-7-yl)oxy)methylmethylcarbonate

40. 1830312-72-5

2.4 Create Date

2017-02-17

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₃F₂N₃O₇S
Molecular Weight	571.6 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	6
Exact Mass	571.12247758 g/mol
Monoisotopic Mass	571.12247758 g/mol
Topological Polar Surface Area	123 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1090
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

For the treatment of influenza A and B virus infection, in patients 12 and older who have been symptomatic for no more than 48 hours. Clinical trials of this drug did not include subjects 65 years of age and older to determine whether they respond in a different way than younger subjects.

FDA Label

* Treatment of influenza:

Xofluza is indicated for the treatment of uncomplicated influenza in patients aged 12 years and above.

* Post exposure prophylaxis of influenza:

Xofluza is indicated for post-exposure prophylaxis of influenza in individuals aged 12 years and above. Xofluza should be used in accordance with official recommendations.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Baloxavir marboxil is a selective inhibitor of influenza cap-dependent endonuclease which prevents polymerase function and therefore influenza virus mRNA replication,. It has shown therapeutic activity against influenza A and B virus infections, including strains resistant to current antiviral agents. This drug inhibits an enzyme required for viral replication, thus rapidly treating flu virus infection, and alleviating the symptoms associated with infection. A single dose of this agent was shown to be superior to placebo in relieving influenza symptoms and superior to both oseltamivir and placebo drug in virologic outcomes (marked by decreased viral load). The safety profile of Baloxavir marboxil compared favorably with that of oseltamivir, making it an effective treatment option for treatment of the flu virus, in one single dose,.

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.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Polymerase Acidic Endonuclease Inhibitor [EPC]; Polymerase Acidic Endonuclease Inhibitors [MoA]; Chelating Activity [MoA]

5.4 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AX - Other antivirals

J05AX25 - Baloxavir marboxil

5.5 Absorption, Distribution and Excretion

Absorption

Tmax: 4h

Route of Elimination

14.7 % of a single dose is excreted in the urine, and 80.1% excreted in the feces

Volume of Distribution

1180 (V/F, L).

Clearance

10.3 L/h

5.6 Metabolism/Metabolites

Baloxavir marboxil is a prodrug that is converted by hydrolysis to baloxavir, the active form that exerts anti-influenza virus activity.

5.7 Biological Half-Life

Terminal elimination half-life: 79.1 h.

5.8 Mechanism of Action

This drug is a CAP endonuclease inhibitor. The influenza endonuclease is an essential subdomain of the viral RNA polymerase enzyme. CAP endonuclease processes host pre-mRNAs to serve as primers for viral mRNA and therefore has been a common target for studies of anti-influenza drugs. Inhibiting the activity of endonuclease can block the transcription of mRNA and inactivate the influenza virus. Viral gene transcription is primed by short-capped oligonucleotides that are cleaved from host cell pre mRNA by endonuclease activity. Translation of viral mRNAs by the host ribosome requires that they are capped at the 5' end, and this is achieved in cells infected with influenza virus by a cap-snatching mechanism, whereby the endonuclease cleaves 5 caps from host mRNA which then act as primers for transcription. The N-terminal domain of PA subunit (PAN) has been confirmed to accommodate the endonuclease activity residues, which is highly preserved among subtypes of influenza A virus and is able to fold functionally. Translation of viral mRNAs by the host ribosome requires that they are capped at the 5' end, and this is achieved in cells infected with influenza virus by a cap-snatching mechanism, whereby the endonuclease cleaves 5 caps from host mRNA which then act as primers for transcription. The endonuclease domain binds the N-terminal half of PA (PAN) and contains a two-metal (Mn2+) active site that selectively cleaves the pre-mRNA substrate at the 3 end of a guanine. The administration of a cap-endonuclease inhibitor, such as Baloxavir marboxil, prevents the above process from occurring, exhibiting its action at the beginning of the pathway before CAP endonuclease may exert its action.

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