U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Sources: Panisheva, E.K.; Mikerova, N.I.; Nikolaeva, I.S.; Fomina, A.N.; Cherkasova, A.A.; Golovanova, E.A.; Krylova, L.Y. Chem. Pharm. J. (Russian), 1988, 21, 1455.
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/18393857

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARBIDOL

Approved Use

Prevention and treatment in adults and children: --Influenza A and B, Avian or Bird Flu, RSV, SARS (including exacerbation of bronchitis and pneumonia) --Secondary immunodeficiency --Overall therapy for chronic bronchitis, pneumonia and recurrent herpes infections --Prevention of post-operative infections and stabilization of immune status --Overall therapy of acute rotavirus- type intestinal infections in children over 2 years old.
PubMed

PubMed

TitleDatePubMed
Arbidol: a broad-spectrum antiviral compound that blocks viral fusion.
2008
Arbidol as a broad-spectrum antiviral: an update.
2014 Jul
Patents

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
An umifenovir (arbidol) concentration of 20μg/ml was required to achieve a 50% reduction in virus proliferation and hemagglutinin levels.
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:57:53 GMT 2023
Edited
by admin
on Sat Dec 16 15:57:53 GMT 2023
Record UNII
93M09WW4RU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UMIFENOVIR
INN   WHO-DD  
INN  
Official Name English
umifenovir [INN]
Common Name English
1-METHYL-2-((PHENYLTHIO)METHYL)-3-CARBETHOXY-4-((DIMETHYLAMINO)METHYL)-5-HYDROXY-6-BROMINDOLE
Common Name English
ARBIDOL
Common Name English
1H-INDOLE-3-CARBOXYLIC ACID, 6-BROMO-4-((DIMETHYLAMINO)METHYL)-5-HYDROXY-1-METHYL-2-((PHENYLTHIO)METHYL)-, ETHYL ESTER
Common Name English
Umifenovir [WHO-DD]
Common Name English
ETHYL 6-BROMO-4-((DIMETHYLAMINO)METHYL)-5-HYDROXY-1-METHYL-2-((PHENYLSULFANYL)METHYL)-1H-INDOLE-3-CARBOXYLATE
Systematic Name English
Classification Tree Code System Code
WHO-ATC J05AX13
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
Code System Code Type Description
WIKIPEDIA
ARBIDOL
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
FDA UNII
93M09WW4RU
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
INN
9271
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL1214598
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID60895015
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
DRUG CENTRAL
4868
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
CAS
131707-25-0
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
SMS_ID
100000153402
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
MESH
C086979
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
NCI_THESAURUS
C152799
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
EVMPD
SUB127507
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
DRUG BANK
DB13609
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
PUBCHEM
131411
Created by admin on Sat Dec 16 15:57:54 GMT 2023 , Edited by admin on Sat Dec 16 15:57:54 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY