13392-28-4 Usage
Description
Rimantadine, also known as Flumadine, is an orally administered antiviral drug that was used for the prophylaxis and treatment of influenza A. It is an RNA synthesis inhibitor that works by blocking the M2 ion channel, which is essential for the uptake of protons into the virus, allowing acid-promoted viral uncoating. However, due to the emergence of resistance since 2009, it is no longer recommended for the treatment of influenza.
Uses
Used in Pharmaceutical Industry:
Rimantadine is used as an antiviral agent for the prophylaxis and treatment of influenza A. It was effective in shortening the duration and alleviating the symptoms of influenza. However, due to the development of resistance, its use has been discontinued since 2009.
Used in Research and Development:
Rimantadine is used in research to study the mechanisms of action and resistance in influenza A viruses. Understanding the role of the M2 protein and its ion channel in the susceptibility of the virus to Rimantadine can help in the development of new antiviral drugs and strategies to combat resistant strains.
References
https://www.drugbank.ca/drugs/DB00478
https://en.wikipedia.org/wiki/Rimantadine
Pharmaceutical Applications
An analog of amantadine, supplied as the hydrochloride for
oral administration.
Mechanism of action
Rimantadine 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.
Pharmacokinetics
Oral 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.
Metabolism
In contrast to amantadine, rimantadine is extensively metabolized in the liver by hydroxylation and glucuronidation.
Excretion
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 Use
rimantadine is used for the treatment
of diseases caused by influenza A strains.
Clinical Use
Prophylaxis and treatment of influenza A H1N1 infections
Since prolonged administration is well tolerated by elderly
patients, the drug is preferable to amantadine.
Side effects
Rimantadine 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.
Check Digit Verification of cas no
The CAS Registry Mumber 13392-28-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,3,9 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13392-28:
(7*1)+(6*3)+(5*3)+(4*9)+(3*2)+(2*2)+(1*8)=94
94 % 10 = 4
So 13392-28-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H21N/c13-2-1-12-6-9-3-10(7-12)5-11(4-9)8-12/h9-11H,1-8,13H2
13392-28-4Relevant articles and documents
Approaches to primary tert-alkyl amines as building blocks
Tzitzoglaki, Christina,Drakopoulos, Antonios,Konstantinidi, Athina,Stylianakis, Ioannis,Stampolaki, Marianna,Kolocouris, Antonios
, (2019/07/10)
Primary tert-alkyl amines include analogues of amantadine, a fragment commonly linked to pharmacophoric groups to enhance biological activity. The preparation of primary tert-alkyl amines is considered to be a difficult problem. Four synthetic procedures, some of which have been previously reported for the synthesis of amines with primary (RCH2NH2) or secondary (RR'CHNH2) alkyl and/or aryl groups, were tested for the synthesis of primary tert-alkyl amines (RR′R″CNH2) in aliphatic series including adamantane adducts. These procedures included the formation and reduction of tert-alkyl azides, the Ritter reaction in standard and modified conditions, the addition of organometallic reagents to N-tert-butyl sulfinyl ketimines and one-pot reactions between nitriles and organometallic reagents in the presence of a Lewis acid, Τi(iPrO)4 or CeCl3. These synthetic routes are unexplored for primary tert-alkyl amines. Studies on the synthetic routes for primary tert-alkyl amines are currently lacking. The reaction conditions and substrate limitations were studied for each procedure, with the first procedure being the most general and applicable also for compounds bearing bulky adducts.
Compounding agent of rimantadine hydrochloride and camphor tree essential oil and application thereof
-
Page/Page column 5-9, (2019/01/24)
The invention discloses a compounding agent of rimantadine hydrochloride and camphor tree essential oil and application thereof, wherein the weight ratio of the amantadine hydrochloride to the camphortree essential oil in the compounding agent is 1: 50-50: 1, Adamantanecarbonyl chloride as a raw material, trimethylaluminum as a reagent and cerium formate as an auxiliary agent are reacted to formadamantane methyl ketone, and the rimantadine hydrochloride is prepared by oximation and platinum-carbon hydrogenation reduction of the adamantane methyl ketone; and the camphor tree essential oil isprepared by crushing camphor tree seeds, leaves, bark and the like as raw materials, using sodium glycinate and citric acid to assist breaking of cell walls and using a distillation technique; and thebeneficial effects are that: high purity and high yield of the rimantadine hydrochloride and the camphor tree essential oil. The compound composition of the rimantadine hydrochloride and the camphortree essential oil has synergistic effect, can effectively reduce the application amount of single agents, expands the sterilization spectrum, reduces the phytotoxicity, significantly improves the control effect against pathogens and viruses, alleviates the resistance problem of pathogenic bacteria, and reduces the cost of prevention.
Optical resolution of rimantadine
Han, Jianlin,Takeda, Ryosuke,Sato, Tatsunori,Moriwaki, Hiroki,Abe, Hidenori,Izawa, Kunisuke,Soloshonok, Vadim A.
, (2019/05/24)
This work discloses a new procedure for the resolution of commercially available racemic rimantadine hydrochloride to enantiomerically pure (S)-rimantadine using (R)-phenoxypropionic acid as a recyclable resolving reagent. Good chemical yields, operational ease, and low-cost structure underscore the preparative value of this method for the production of enantiomerically pure rimantadine for medicinal or synthetic studies.
