Rimantadine Chemical Properties
- Boiling point:248°C
- Density 1.033
- Flash point:99°C
- CAS DataBase Reference13392-28-4(CAS DataBase Reference)
- NIST Chemistry Reference1-Adamantanemethylamine, «alpha»-methyl-(13392-28-4)
- HazardClass IRRITANT
- Hazardous Substances Data13392-28-4(Hazardous Substances Data)
Rimantadine Usage And Synthesis
- DescriptionRimantadine (Brand name: Flumadine) is a kind of RNA synthesis inhibitor that used as an orally administrated antiviral drug in the prophylaxis and for the treatment of influenza. It is capable of shortening the duration and alleviated the symptoms of influenza. However, it is now not recommended for the treatment of influenza any longer due to the emergence of resistance problem since 2009. Its mechanism of action is not fully understood. It is indicated that it take effects through inhibiting the viral replication through possibly inhibiting the uncoating process of the virus. The virus M2 protein (an ion channel) seems to play an important role in the susceptibility of influenza A virus to the treatment of Rimantadine.
- UsesRimantadine act by blocking the M2 ion channel which is required for uptake of protons into the interior of the virus to permit acid-promoted viral uncoating (decapsidation).
- brand nameFlumadine (Forest).
- General DescriptionResistant variants of influenza type A have been recoveredfrom rimantadine-treated patients.Resistance with inhibitory concentrations increased morethan 100-fold have been associated with single nucleotidechanges that lead to amino acid substitutions in the transmembranedomain of M2. rimantadineshare cross-susceptibility and resistance.
- Pharmaceutical ApplicationsAn analog of amantadine, supplied as the hydrochloride for oral administration.
- Mechanism of actionRimantadine hydrochloride (α-methyl-1-adamantanemethylamine hydrochloride) is a synthetic adamatane derivative that is structurally and pharmacologically related to amantadine. It appears to be more effective than amantadine hydrochloride against influenza A, with fewer CNS side effects. Rimantadine hydrochloride is thought to interfere with virus uncoating by inhibiting the release of specific proteins. It may act by inhibiting RT or the synthesis of virus-specific RNA, but it does not inhibit virus adsorption or penetration. It appears to produce a virustatic effect early in the virus replication. It is used widely in Russia and Europe.
- PharmacokineticsOral absorption: >90%
Cmax 100 mg oral (every 12 h): 0.4–0.5 mg/L after 2–6 h
Plasma half-life: c. 35 h
Volume of distribution: Very large
Plasma protein binding: c. 40%
Absorption and distribution
Single- and multiple-dose pharmacokinetic studies in elderly patients and young adults are remarkably similar. The steadystate concentration in nasal mucus develops by day 5 at a concentration approximately 1.5-fold higher than plasma.
In contrast to amantadine, rimantadine is extensively metabolized in the liver by hydroxylation and glucuronidation.
Less than 20% is excreted unchanged in the urine and most of the breakdown products are excreted by this route. Thus, the plasma half-life is much less affected by renal dysfunction than that of amantadine.
- Clinical Userimantadine is used for the treatment of diseases caused by influenza A strains.
- Clinical UseProphylaxis and treatment of influenza A H1N1 infections Since prolonged administration is well tolerated by elderly patients, the drug is preferable to amantadine.
- Side effectsRimantadine has significantly fewer side effects than amantadine at equivalent doses, perhaps because of differences in pharmacokinetics, since with equal doses the blood levels are considerably lower. CNS side effects are not significantly higher than placebo.
Rimantadine Preparation Products And Raw materials
- ADAMANTAN-1-YL-(4-PROPYL-BENZENESULFONYLAMINO)-ACETIC ACID AKOS B006184 ADAMANTAN-1-YL-(4-ISOPROPYL-BENZENESULFONYLAMINO)-ACETIC ACID N-[1-(1-ADAMANTYL)ETHYL]-2-NITRO-5-(1-PIPERAZINYL)ANILINE AKOS BC-0753 AKOS BC-0865 (1-ADAMANTAN-1-YL-ETHYL)-PYRIDIN-4-YLMETHYL-AMINE HYDROCHLORIDE 1-(1-ISOTHIOCYANATO-ETHYL)-ADAMANTANE (1-ADAMANTAN-1-YL-ETHYL)-PYRIDIN-3-YL-METHYL-AMINE HYDROCHLORIDE 3-([[1-(1-ADAMANTYL)ETHYL]AMINO]SULFONYL)BENZOIC ACID methyl 1-adamantyl(amino)acetate 1-ADAMANTYL(PHENYL)METHANAMINE N-[1-(1-adamantyl)ethyl]-2-cyanoacetamide Rimantadine Adamantane 1-Adamantaneacetic acid 1-Adamantanecarboxylic acid RIMANTADINE HYDROCHLORIDE,RIMANTADINE HCL,1-(Adamantan-1-yl)ethylamine hydrochloride, Rimantadine hydrochloride,ALPHA-METHYL-1-ADAMANTANEMETHYLAMINE HYDROCHLORIDE
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