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Umifenovir

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Also known as: Umifenovir, 131707-25-0, Umifenovir [inn], Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate, Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1h-indole-3-carboxylate, Mls000777586

Molecular Formula

C₂₂H₂₅BrN₂O₃S

Molecular Weight

477.4 g/mol

InChI Key

KCFYEAOKVJSACF-UHFFFAOYSA-N

FDA UNII

93M09WW4RU

Umifenovir is an orally bioavailable indole derivative, with broad-spectrum antiviral and potential anti-inflammatory activities. Upon oral administration, umifenovir inhibits the fusion of the viral envelope with host cell membrane, thereby blocking the entry of virus into host cells and preventing viral infection and replication. Umifenovir may also suppress the expression of the cytokines interleukin-1beta (IL-1b), IL-6, IL-12 and tumor necrosis factor-alpha (TNF-a) and promote the expression of IL-10. This may reduce inflammation.

1 2D Structure

Umifenovir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate

2.1.2 InChI

InChI=1S/C22H25BrN2O3S/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3/h6-11,26H,5,12-13H2,1-4H3

2.1.3 InChI Key

KCFYEAOKVJSACF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOC(=O)C1=C(N(C2=CC(=C(C(=C21)CN(C)C)O)Br)C)CSC3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

93M09WW4RU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-methyl-2-((phenylthio)methyl)-3-carbethoxy-4-((dimethylamino)methyl)-5-hydroxy-6-bromoindole

2. 1h-indole-3-carboxylic Acid, 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-, Ethyl Ester

3. Arbidole

4. Umifenovir

5. Umifenovir Hydrochloride

6. Umifenovir Hydrochloride Monohydrate

7. Umifenovir Sulfoxide

2.3.2 Depositor-Supplied Synonyms

1. Umifenovir

2. 131707-25-0

3. Umifenovir [inn]

4. Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate

5. Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1h-indole-3-carboxylate

6. Mls000777586

7. 93m09ww4ru

8. Umifenovir (inn)

9. 1h-indole-3-carboxylic Acid, 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-, Ethyl Ester

10. Smr000413980

11. 1h-indole-3-carboxylic Acid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, Ethyl Ester

12. Unii-93m09ww4ru

13. Arbidol Base

14. 6-bromo-4-dimethylaminomethyl-5-hydroxy-1-methyl-2-phenylsulfanylmethyl-1h-indole-3-carboxylic Acid Ethyl Ester

15. 75u

16. Ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylsulfanyl)methyl)-1h-indole-3-carboxylate

17. Arbidol; Umifenovir

18. Ar-1i9514

19. Chemdiv1_000732

20. Umifenovir [who-dd]

21. Oprea1_384852

22. Oprea1_482224

23. Mls006011808

24. Cid_131411

25. Schembl1068701

26. Chembl1214598

27. Bdbm83797

28. Gtpl11089

29. Hms589b06

30. Dtxsid60895015

31. Chebi:134730

32. Hms2760j21

33. Albb-028966

34. Bcp04187

35. Ex-a3050

36. Mfcd01326495

37. Stk021887

38. Zinc19907652

39. Akos001485435

40. At13213

41. Db13609

42. Dt-0014

43. Ncgc00246387-01

44. Ncgc00246387-02

45. Ncgc00246387-06

46. Ncgc00246387-09

47. Ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-1h-indole-3-carboxylate

48. Ethyl 6-bromo-4-(dimethylaminomethyl)-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate

49. Ethyl 6-bromo-5-hydroxy-1-methyl-4-((dimethylamino)methyl)-2-[(phenylthio)methyl]-1h-indole-3-carboxylate

50. Hy-14904

51. Cs-0003625

52. D10558

53. Ab00644670_06

54. A888382

55. Q27271599

56. 1-methyl-2-((phenylthio)methyl)-3-carbethoxy-4-((dimethylamino)methyl)-5-hydroxy-6-bromindole

57. 1h-indole-3-carboxylic Acid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, Ethyl Ester, Hydrochloride

58. 5674-91-9

59. 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-3-indolecarboxylic Acid Ethyl Ester

60. 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]indole-3-carboxylic Acid Ethyl Ester

61. 6-bromo-4-dimethylaminomethyl-5-hydroxy-1-methyl-2-phenylsulfanylmethyl-1h-indole-3-carboxylic Acid Ethyl Ester

62. 6-bromo-5-hydroxy-4-methylaminomethyl-1-methyl-2-benzenesulfenylmethylindole-3-ethyl Carboxylate

63. Ethyl 6-bromanyl-4-[(dimethylamino)methyl]-1-methyl-5-oxidanyl-2-(phenylsulfanylmethyl)indole-3-carboxylate

64. Ethyl 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxilate

2.4 Create Date

2005-07-09

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₅BrN₂O₃S
Molecular Weight	477.4 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	476.07693 g/mol
Monoisotopic Mass	476.07693 g/mol
Topological Polar Surface Area	80 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	546
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Umifenovir is currently licensed in China and Russia for the prophylaxis and treatment of influenza and other respiratory viral infections. It has demonstrated activity against a number of viruses and has been investigated in the treatment of _Flavivirus_, Zika virus, foot-and-mouth disease, Lassa virus, Ebola virus, and herpes simplex. In addition, it has shown _in vitro_ activity against hepatitis B and C viruses, chikungunya virus, reovirus, Hantaan virus, and coxsackie virus B5. Umifenovir is currently being investigated as a potential treatment and prophylactic agent for the prevention of COVID-19 caused by SARS-CoV-2 infections.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Umifenovir exerts its antiviral effects via both direct-acting virucidal activity and by inhibiting one (or several) stage(s) of the viral life cycle. Its broad-spectrum of activity covers both enveloped and non-enveloped RNA and DNA viruses. It is relatively well-tolerated and possesses a large therapeutic window - weight-based doses up to 100-fold greater than those used in humans failed to produce any pathological changes in test animals. Umifenovir does not appear to result in significant viral resistance. Instances of umifenovir-resistant influenza virus demonstrated a single mutation in the HA2 subunit of influenza hemagglutinin, suggesting resistance is conferred by prevention of umifenovirs activity related to membrane fusion. The mechanism through which other viruses may become resistant to umifenovir requires further study.

5.2 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AX - Other antivirals

J05AX13 - Umifenovir

5.3 Absorption, Distribution and Excretion

Absorption

Umifenovir is rapidly absorbed following oral administration, with an estimated T_max between 0.65-1.8 hours. The C_max has been estimated as 415 - 467 ng/mL and appears to increase linearly with dose, and the AUC_0-inf following oral administration has been estimated to be approximately 2200 ng/mL/h.

Route of Elimination

The major route of elimination is via the feces. Approximately 40% of an ingested dose is excreted unchanged, of which 38.9% is excreted in the bile and 0.12% excreted through the kidneys. The total recovery of parent drug and metabolites in the urine accounts for less than 1% of an ingested dose.

Volume of Distribution

Data regarding the volume of distribution of umifenovir are currently unavailable.

Clearance

In a study involving healthy male Chinese volunteers, the oral clearance of umifenovir was found to be 99 34 L/h.

5.4 Metabolism/Metabolites

Umifenovir is highly metabolized in the body, primarily in hepatic and intestinal microsomess, with approximately 33 metabolites having been observed in human plasma, urine, and feces. The principal phase I metabolic pathways include sulfoxidation, N-demethylation, and hydroxylation, followed by phase II sulfate and glucuronide conjugation. In the urine, the major metabolites were sulfate and glucuronide conjugates, while the major species in the feces was unchanged parent drug (~40%) and the M10 metabolite (~3.0%). In the plasma, the principal metabolites are M6-1, M5, and M8 - of these, M6-1 appears of most importance given its high plasma exposure and long elimination half-life (~25h), making it a potentially important player in the safety and efficacy of umifenovir. Enzymes involved in the metabolism of umifenovir include members of the cytochrome P450 family (primarily CYP3A4), flavin-containing monooxygenase (FMO) family, and UDP-glucuronosyltransferase (UGT) family (specifically UGT1A9 and UGT2B7).

Arbidol has known human metabolites that include (2S,3S,4S,5R)-6-[6-bromo-4-[(dimethylamino)methyl]-3-ethoxycarbonyl-1-methyl-2-(phenylsulfanylmethyl)indol-5-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.5 Biological Half-Life

The half-life of umifenovir following oral administration has been estimated to be between 17-21 hours. Serum half-lives of the M5, M6-1, and M8 metabolites were found to be 26.3 5.9, 25.0 5.4, and 25.7 8.8, respectively.

5.6 Mechanism of Action

Umifenovir is considered both a direct-acting antiviral (DAA) due to direct virucidal effects and a host-targeting agent (HTA) due to effects on one or multiple stages of viral life cycle (e.g. attachment, internalization), and its broad-spectrum antiviral activity is thought to be due to this dual activity. It is a hydrophobic molecule capable of forming aromatic stacking interactions with certain amino acid residues (e.g. tyrosine, tryptophan), which contributes to its ability to directly act against viruses. Antiviral activity may also be due to interactions with aromatic residues within the viral glycoproteins involved in fusion and cellular recognition, with the plasma membrane to interfere with clathrin-mediated exocytosis and intracellular trafficking, or directly with the viral lipid envelope itself (in enveloped viruses). Interactions at the plasma membrane may also serve to stabilize it and prevent viral entry (e.g. stabilizing influenza hemagglutinin inhibits the fusion step necessary for viral entry). Due to umifenovirs ability to interact with both viral proteins and lipids, it may also interfere with later stages of the viral life cycle. Some virus families, such as _Flaviviridae_, replicate in a subcellular compartment called the membranous web - this web requires lipid-protein interactions that may be hindered by umifenovir. Similarly, viral assembly of hepatitis C viruses is contingent upon the assembly of lipoproteins, presenting another potential target.

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