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Details

Stereochemistry ACHIRAL
Molecular Formula C22H25BrN2O3S
Molecular Weight 477.415
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UMIFENOVIR

SMILES

CCOC(=O)C1=C(CSC2=CC=CC=C2)N(C)C3=C1C(CN(C)C)=C(O)C(Br)=C3

InChI

InChIKey=KCFYEAOKVJSACF-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H25BrN2O3S
Molecular Weight 477.415
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Umifenovir or arbidol (ethyl-6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-indole-3-carboxylate hydrochloride monohydrate) is a Russian-made potent broad-spectrum antiviral with demonstrated activity against a number of enveloped and non-enveloped viruses.For both viral infections the anti-viral mechanism involves umifenovir inhibition of virus-mediated fusion with target membrane and a resulting block of virus entry into target cells. Arbidol was shown to have effects on nonspecific defense factors, on its capacity to induce interferon and activate phagocytes in particular. Arbidol-treated patients with lower baseline immunity showed improvement in immunological parameters (in the counts of CD4 and CD8 lymphocytes, B lymphocytes, in the levels of serum immunoglobulins). Arbidol produces a high preventive and therapeutical effects in influenza A and B and other acute respiratory viral infections, prevents postinfluenza complications, reduces the incidence of exacerbations of chronic diseases in postinfluenza patients. In influenza, the therapeutical efficiency of the drug appears as decreases in intoxication, the severity of catarrhal syndrome, shorter fever and disease in general. Arbidol is beneficial for patients with secondary immunodeficiency, in those with recurrent herpes infection or chronic bronchitis.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARBIDOL

Cmax

ValueDoseCo-administeredAnalytePopulation
467 ng/mL
200 mg single, oral
UMIFENOVIR plasma
Homo sapiens
0.7 mg/L
0.2 g single, oral
UMIFENOVIR plasma
Homo sapiens
1.24 mg/L
0.4 g single, oral
UMIFENOVIR plasma
Homo sapiens
2.16 mg/L
0.8 g single, oral
UMIFENOVIR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2203 ng × h/mL
200 mg single, oral
UMIFENOVIR plasma
Homo sapiens
3.27 mg × day/L
0.2 g single, oral
UMIFENOVIR plasma
Homo sapiens
5.81 mg × day/L
0.4 g single, oral
UMIFENOVIR plasma
Homo sapiens
12.72 mg × day/L
0.8 g single, oral
UMIFENOVIR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
15.7 h
200 mg single, oral
UMIFENOVIR plasma
Homo sapiens

Doses

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Directions for Use: For internal use, to be taken on an empty stomach. Single dose amount: Children 2 - 7 years, 50 mg; 7 – 12 years, 100 mg; 12 – adult, 200 mg (1 - 200 mg capsule, 2 – 100 mg capsules, or 4 - 50 mg capsules). For non-specific prophylaxis: During direct contact with patients with influenza or RSV, children 2 – 7, 50 mg; children 7 – 12, 100 mg; 12 to adult, 200 mg, once a day for 10 to 14 days. During influenza or other RSV epidemics, or in order to prevent exacerbation of chronic bronchitis, or recurrent herpes infection, the dosage is children 2 – 7, 50 mg; children 7 – 12, 100 mg; and over 12 to adult, 200 mg, twice a week for three weeks. For SARS prophylaxis (during contact with SARS patients), the dosage for children over 12 – adult is 200 mg once a day; for children from 7 to 12, 100 mg, taken before food, once a day for 12 – 14 days. For prophylaxis against postoperative complications: children 2 – 7, 50 mg; children 7 – 12, 100 mg; children over 12 – adult, 200 mg 48 hours before the procedure, then from 2 to 5 days after the procedure. For treatment of illness: For influenza, or other uncomplicated RSV, children 2 – 7, 50 mg; children 7 – 12, 100 mg, and children over 12 and adults, 200 mg, 4 times a day (every 6 hours) for 5 days. For influenza with complications (bronchitis, pneumonia), children 2 – 7, 50 mg; children 7 – 12, 100 mg; children over 12 and adults, 200 mg, 4 times a day (every 6 hours) for 5 days, then one dose per week for the next four weeks. For Severe Acute Respiratory Syndrome (SARS), in children over 12 and adults, 200 mg twice a day for 8 – 10 days. For chronic bronchitis or herpes-type infections, in children 2 – 7 years, 50 mg; children 7 – 12, 100 mg; children over 12 and adults, 200 mg 4 times a day (every 6 hours) for 5 – 7 days; thereafter, one dose twice a week for the next 4 weeks. For treatment of acute intestinal infections of the rotavirus-type, in children over 2 years old, give 50 mg; children 7 – 12, 100 mg; and children over 12, 200 mg, four times a day (every 6 hours) for 5 days.
Route of Administration: Oral
In Vitro Use Guide
An umifenovir (arbidol) concentration of 20μg/ml was required to achieve a 50% reduction in virus proliferation and hemagglutinin levels.
Substance Class Chemical
Record UNII
93M09WW4RU
Record Status Validated (UNII)
Record Version