Rimantadine

Base Information

• Chemical Name: Rimantadine
• CAS No.: 13392-28-4
• Molecular Formula: C₁₂H₂₁N
• Molecular Weight: 179.305
• Hs Code.: 2921300090
• UNII: 0T2EF4JQTU
• DSSTox Substance ID: DTXSID2023561
• Nikkaji Number: J8.105A
• Wikipedia: Rimantadine
• Wikidata: Q42171
• NCI Thesaurus Code: C61927
• RXCUI: 9386
• Metabolomics Workbench ID: 42824
• ChEMBL ID: CHEMBL959,CHEMBL1201272
• Mol file: 13392-28-4.mol

Synonyms:Flumadine;Hydrochloride, Rimantadine;Remantadine;Riamantadine;Rimantadine;Rimantadine Hydrochloride;Roflual

Chemical Property of Rimantadine

Chemical Property:

• Vapor Pressure: 0.0249mmHg at 25°C
• Refractive Index: 1.539
• Boiling Point: 247.8 °C at 760 mmHg
• PKA: 11.17±0.29(Predicted)
• Flash Point: 99.3 °C
• PSA: 26.02000
• Density: 1.033 g/cm³
• LogP: 4.05230
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 179.167399674
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

1-Adamantanemethylamine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(C12CC3CC(C1)CC(C3)C2)N
• Recent ClinicalTrials: A Pharmacokinetic Study on Co-administration of Tamiflu (Oseltamivir) and Rimantadine in Healthy Volunteers
• Description: Rimantadine (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.
• Uses: Rimantadine 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).
• Clinical Use: rimantadine is used for the treatment of diseases caused by influenza A strains. Prophylaxis and treatment of influenza A H1N1 infections Since prolonged administration is well tolerated by elderly patients, the drug is preferable to amantadine.

Technology Process of Rimantadine

There total 16 articles about Rimantadine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

rimantadine hydrochloride (1501-84-4,33122-80-4,33122-81-5,33298-76-9) → rimantadine (13392-28-4,117857-51-9,117857-52-0,129277-01-6)

Guidance literature:

With sodium hydroxide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.3390/molecules24091828

Reference yield: 96.0%

1-adamantyl methyl ketoxime (78679-71-7) → rimantadine (13392-28-4,117857-51-9,117857-52-0,129277-01-6)

Guidance literature:

Pt/C; In water; acetic acid;

Reference yield: 95.0%

1-((3r,5r,7r)-adamantan-1-yl)ethan-1-one oxime (1707-40-0) → rimantadine (13392-28-4,117857-51-9,117857-52-0,129277-01-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; acetic acid; tartaric acid; at 20 ℃; for 18h; under 3000.3 Torr; Pressure; Reagent/catalyst; Autoclave; Green chemistry;

upstream raw materials:

1-((3r,5r,7r)-adamantan-1-yl)ethan-1-one oxime

propyl cyanide

1-acetyladamantane

benzonitrile

Downstream raw materials:

C₂₀H₂₇NO₂

C₂₀H₂₉NO₂

2-((1-(1-adamantan-1-yl)ethyl)-imino-methyl)-6-methoxyphenol

adamantyl-N-(ethyl)-(5-chlorosalicylidene)aniline

Refernces

• 1、 -. "Compounding agent of rimantadine hydrochloride and camphor tree essential oil and application thereof". Page/Page column 5-9. . Retrieved 2019/01/24.
• 2、 Han, Jianlin,Takeda, Ryosuke,Sato, Tatsunori,Moriwaki, Hiroki,Abe, Hidenori,Izawa, Kunisuke,Soloshonok, Vadim A.. "Optical resolution of rimantadine". . . Retrieved 2019/05/24.