Rimantadine Hydrochloride

Names

[ Name ]:
Rimantadine Hydrochloride

[Synonym ]:
1-(1-Adamantyl)ethylamine Hydrochloride
tricyclo[3.3.1.1]decane-1-methanamine, α-methyl-, hydrochloride
1-(Adamantan-1-yl)ethanamine hydrochloride (1:1)
a-Methyltricyclo[3.3.1.13,7]decane-1-methanamine Hydrochloride
Roflual
1-(tricyclo[3.3.1.1]dec-1-yl)ethanamine hydrochloride (1:1)
Meradan
Tricyclo[3.3.1.1]decane-1-methanamine, α-methyl-, hydrochloride (1:1)
α-Methyl-1-adamantanemethylamine hydrochloride
MFCD00072023
UNII:JEI07OOS8Y
a-Methyl-1-adamantanemethylamine Hydrochloride
1-(Adamantan-1-yl)ethanamine hydrochloride
1-Tricyclo[3.3.1.1]dec-1-ylethanaminhydrochlorid
Alpha-Methyl-1-Adamantanemethylamine Hydrochloride
1-(1-Aminoethyl)adamantane hydrochloride
Tricyclo[3.3.1.13,7]-decane-1-methanamine, .α.-methyl-, hydrochloride
Rimantadine Hydrochloride
1-tricyclo[3.3.1.1]déc-1-yléthanamine chlorhydrate
1-tricyclo[3.3.1.1]dec-1-ylethanamine hydrochloride
Remantadine hydrochloride

Biological Activity

[Description]:

Rimantadine Hcl (Flumadine) is an anti-influenza virus drug.Target: Influenza VirusRimantadine are oral antiviral drugs useful in the prophylaxis and treatment of influenza A virus infections. rimantadine has prophylactic efficacy comparable to amantadine but lower potential for causing adverse effects [1]. double-blind study of children with influenza-like illness. 37 received rimantadine for five days. Of the total 37 children in the rimantadine group, 27% were found to have resistant isolated compared with 6% in the total group receiving acetaminophen (P < .04). Furthermore, the mean inhibitory concentration of rimantadine increased with time in the rimantadine group (r = .4, P = .002) [2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

[References]

[1]. Hall, C.B., et al., Children with influenza A infection: treatment with rimantadine. Pediatrics, 1987. 80(2): p. 275-82.

[2]. Tominack, R.L. and F.G. Hayden, Rimantadine hydrochloride and amantadine hydrochloride use in influenza A virus infections. Infect Dis Clin North Am, 1987. 1(2): p. 459-78.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
247.8ºC at 760mmHg

[ Melting Point ]:
300ºC

[ Molecular Formula ]:
C₁₂H₂₂ClN

[ Molecular Weight ]:
215.763

[ Flash Point ]:
99.3ºC

[ Exact Mass ]:
215.144073

[ PSA ]:
26.02000

[ LogP ]:
4.05230

[ Vapour Pressure ]:
0.0251mmHg at 25°C

[ Water Solubility ]:
Freely soluble in water.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU4717000

CHEMICAL NAME :: 1-Adamantanemethylamine, alpha-methyl-, hydrochloride

CAS REGISTRY NUMBER :: 1501-84-4

LAST UPDATED :: 199803

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H21-N.Cl-H

MOLECULAR WEIGHT :: 215.80

WISWESSER LINE NOTATION :: L66 B6/B-H/DI A B- C 1B ITJ BYZ1 &GH

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 :: 640 mg/kg

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

REFERENCE :: VOONAW Voprosy Onkologii. Problems of Oncology. For English translation, see PONCAU. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-10, 1928-37; V.1- 1955- Volume(issue)/page/year: 28(9),23,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 135 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - ataxia

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,798,1977

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AU4717000

[ HS Code ]:
2921199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2921300090

[ Summary ]:
2921300090 other cyclanic, cyclenic or cyclotherpenic mono- or polyamines, and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

Exploring the proton conductance and drug resistance of BM2 channel through molecular dynamics simulations and free energy calculations at different pH conditions.

J. Phys. Chem. B 117(4) , 982-8, (2013)

BM2 channel plays an important role in the replication of influenza virus B. However, few studies attempt to investigate the mechanism of the proton conductance in BM2 channel, as well as the drug res...

Cys-Loop Receptor Channel Blockers Also Block GLIC

Biophys. J. 101(12) , 2912-8, (2011)

The Gloeobacter ligand-gated ion channel (GLIC) is a bacterial homolog of vertebrate Cys-loop ligand-gated ion channels. Its pore-lining region in particular has a high sequence homology to these rela...

[Susceptibility of pandemic influenza virus A 2009 H1N1 and highly pathogenic avian influenza virus A H5N1 to antiinfluenza agents in cell culture].

Antibiot. Khimioter. 56(3-4) , 3-9, (2011)

The data on cytotoxicity and antiviral activity of commercial antivirals, such as Remantadine, Oseltamivir, Arbidol and Ribavirin in the MDCK cell culture infected with highly pathogenic (H5N1) and pa...