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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
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 Weight 477.4 g/mol
Molecular Formula C22H25BrN2O3S
XLogP34.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass476.07693 g/mol
Monoisotopic Mass476.07693 g/mol
Topological Polar Surface Area80 Ų
Heavy Atom Count29
Formal Charge0
Complexity546
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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 Tmax between 0.65-1.8 hours. The Cmax has been estimated as 415 - 467 ng/mL and appears to increase linearly with dose, and the AUC0-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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12-Jan-2021
06-Oct-2024
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ABOUT THIS PAGE

Looking for 131707-25-0 / Arbidol hydrochloride API manufacturers, exporters & distributors?

Arbidol hydrochloride manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Arbidol hydrochloride API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Arbidol hydrochloride manufacturer or Arbidol hydrochloride supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Arbidol hydrochloride manufacturer or Arbidol hydrochloride supplier.

PharmaCompass also assists you with knowing the Arbidol hydrochloride API Price utilized in the formulation of products. Arbidol hydrochloride API Price is not always fixed or binding as the Arbidol hydrochloride Price is obtained through a variety of data sources. The Arbidol hydrochloride Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Arbidol hydrochloride

Synonyms

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

Cas Number

131707-25-0

Unique Ingredient Identifier (UNII)

93M09WW4RU

About Arbidol hydrochloride

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.

Umifenovir Manufacturers

A Umifenovir manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Umifenovir, including repackagers and relabelers. The FDA regulates Umifenovir manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Umifenovir API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Umifenovir manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Umifenovir Suppliers

A Umifenovir supplier is an individual or a company that provides Umifenovir active pharmaceutical ingredient (API) or Umifenovir finished formulations upon request. The Umifenovir suppliers may include Umifenovir API manufacturers, exporters, distributors and traders.

click here to find a list of Umifenovir suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Umifenovir NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Umifenovir as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Umifenovir API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Umifenovir as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Umifenovir and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Umifenovir NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Umifenovir suppliers with NDC on PharmaCompass.

Umifenovir GMP

Umifenovir Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Umifenovir GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Umifenovir GMP manufacturer or Umifenovir GMP API supplier for your needs.

Umifenovir CoA

A Umifenovir CoA (Certificate of Analysis) is a formal document that attests to Umifenovir's compliance with Umifenovir specifications and serves as a tool for batch-level quality control.

Umifenovir CoA mostly includes findings from lab analyses of a specific batch. For each Umifenovir CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Umifenovir may be tested according to a variety of international standards, such as European Pharmacopoeia (Umifenovir EP), Umifenovir JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Umifenovir USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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