Arbidol HCl

Names

[ Name ]:
Arbidol HCl

[Synonym ]:
1-methyl-2-phenylthiomethyl-3-carbethoxy-4-dimetylaminomethyl-5-hydroxy-6-bromoindole hydrogen chloride
Arbidol Hydrochloride
6-Bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-1H-indole-3-carboxylic Acid Ethyl Ester Moonohydrochloride
Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate hydrochloride (1:1)
1-methyl-2-phenylthiomethyl-3-carbethoxy-4-dimethylaminomethyl-5-oxy-6-bromindol hydrochloride
Arbidol Hydrochloride Hydrate
arbidol hydrogen chloride
1H-Indole-3-carboxylic acid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, ethyl ester, hydrochloride (1:1)
umifenovir hydrogen chloride
Arbidol HCl
MFCD00333871
Arbidol
umifenovir hydrochloride
Arbidol (hydrochloride)

Biological Activity

[Description]:

Arbidol (Umifenovir) hydrochloride is an broad-spectrum antiviral chemical agent which can inhibit cell entry of enveloped viruses by blocking viral fusion with host cell membraneIC50 value:Target: Antiviral; Anti-influenza agentin vitro: Arbidol was found to present potent inhibitory activity against enveloped and non-enveloped RNA viruses, including FLU-A, RSV, HRV 14 and CVB3 when added before, during, or after viral infection, with 50% inhibitory concentration (IC50) ranging from 2.7 to 13.8 microg/ml.However, arbidol showed selective antiviral activity against AdV-7, a DNA virus, only when added after infection (therapeutic index (TI) = 5.5) [1]. Arb interacts with the polar head-group of phospholipid at the membrane interface. Fluorescence studies of interactions between Arb and either tryptophan derivatives or membrane peptides reconstituted into liposomes show that Arb interacts with tryptophan in the micromolar range. Interestingly, apparent binding affinities between lipids and tryptophan residues are comparable with those of Arb IC50 of the hepatitis C virus (HCV) membrane fusion [2]. Arbidol not only prevented the cytopathic effect (CPE) of CVB(5), as demonstrated in an MTT colorimetric assay, when added during or after viral infection, with a 50% inhibitory concentration (IC(50)) from 2.66 to 6.62 microg/ml, but it also decreased the CVB(5)-RNA level in infected host cells, as shown in semi-quantitative RT-PCR [3].in vivo: Orally administered arbidol at 50 or 100 mg/kg/day beginning 24 h pre-virus exposure for 6 days significantly reduced mean pulmonary virus yields and the rate of mortality in mice infected with FLU-A (A/PR/8/34 H1N1) [1]. BALB/c mice were used as an animal model to test the Arbidol activity in vivo. Orally administered Arbidol at 50 mg/kg body weight/day (once a day) significantly reduced mean virus yields in the lungs and heart as well as mortality after infection for 6 days [3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

[References]

[1]. Shi L, et al. Antiviral activity of arbidol against influenza A virus, respiratory syncytial virus, rhinovirus, coxsackie virus and adenovirus in vitro and in vivo. Arch Virol. 2007;152(8):1447-55.

[2]. Teissier E, et al. Mechanism of inhibition of enveloped virus membrane fusion by the antiviral drug arbidol. PLoS One. 2011 Jan 25;6(1):e15874.

[3]. Zhong Q, et al. Antiviral activity of Arbidol against Coxsackie virus B5 in vitro and in vivo. Arch Virol. 2009;154(4):601-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
591.8ºC at 760 mmHg

[ Melting Point ]:
133-137ºC

[ Molecular Formula ]:
C₂₂H₂₆BrClN₂O₃S

[ Molecular Weight ]:
513.875

[ Flash Point ]:
311.7℃

[ Exact Mass ]:
512.053589

[ PSA ]:
80.00000

[ LogP ]:
5.97900

[ Vapour Pressure ]:
1.34E-14mmHg at 25°C

[ Storage condition ]:
Hygroscopic, Refrigerator, Under Inert Atmosphere

[ Stability ]:
Hygroscopic

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL5998075

CHEMICAL NAME :: 1H-Indole-3-carboxylic acid, 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl- 2- ((phenylthio)methyl)-, ethyl ester, monohydrochloride, hydrate

CAS REGISTRY NUMBER :: 131707-23-8

LAST UPDATED :: 199312

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C22-H25-Br-N2-O3-S.Cl-H.H2-O

MOLECULAR WEIGHT :: 531.94

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 17,1079,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 340 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 17,1079,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 17,1079,1992

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

[Potentiation of NO-dependent activation of soluble guanylyl cyclase by 5-nitroisatin and antiviral preparatation arbidol].

Biomed. Khim. 59(3) , 295-304, (2013)

Isatin (indole-dione) is an endogenous indole that exibits a wide range of biological and physiological activity. The influence of isatin derivatives 5-nitroisatin and arbidol (an antiviral preparatat...

Arbidol exhibits strong inhibition towards UDP-glucuronosyltransferase (UGT) 1A9 and 2B7.

Pharmazie 68(12) , 945-50, (2013)

The aim of the present study was to investigate arbidol's inhibition towards UDP-glucuronosyltransferase (UGT) 1A9 and 2B7. The nonspecific probe substrate 4-methylumbelliferone (4-MU) and recombinant...

Pharmacokinetics, metabolism, and excretion of the antiviral drug arbidol in humans.

Antimicrob. Agents Chemother. 57(4) , 1743-55, (2013)

Arbidol is a broad-spectrum antiviral drug that is used clinically to treat influenza. In this study, the pharmacokinetics, metabolism, and excretion of arbidol were investigated in healthy male Chine...