1-AdaMantanethylaMine Chemical Properties

Boiling point:

248°C

Density 

1.033

Flash point:

99°C

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

form 

Liquid

pka

11.17±0.29(Predicted)

color 

Colorless to light yellow

CAS DataBase Reference

13392-28-4(CAS DataBase Reference)

NIST Chemistry Reference

1-Adamantanemethylamine, «alpha»-methyl-(13392-28-4)

Safety Information

HazardClass 

IRRITANT

HS Code 

2902190000

Hazardous Substances Data

13392-28-4(Hazardous Substances Data)

1-AdaMantanethylaMine Usage And Synthesis

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.

References

https://www.drugbank.ca/drugs/DB00478
https://en.wikipedia.org/wiki/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).

Definition

ChEBI: 1-(1-adamantyl)ethanamine is an alkylamine.

brand name

Flumadine (Forest).

General Description

Resistant 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 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%
C_max 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

Prophylaxis and treatment of influenza A H1N1 infections Since prolonged administration is well tolerated by elderly patients, the drug is preferable to amantadine.

Clinical Use

rimantadine is used for the treatment of diseases caused by influenza A strains.

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.

1-AdaMantanethylaMine(13392-28-4)Related Product Information

• Amantadine
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• 1-Adamantanecarboxylic acid
• Ethylamine
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• Levofloxacin hydrochloride
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• Tricyclo[3.3.1.13,7]decane-1-methanamine, α-(1-methylethyl)-
• Rimantadine hydrochloride
• RIMANTADINE HCL USP(CRM STANDARD),RIMANTADINE-D4 HCL (ETHYL-D4) 98.5%
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• Fluorine
• Levofloxacin
• Hydrochloric acid
• Flunarizine
• Oxygen
• Rimantadine