Tromantadine is an antiviral medicine used to treat

herpes simplex virus Herpes simplex virus 1 and 2 (HSV-1 and HSV-2), also known by their taxonomical names ''Human alphaherpesvirus 1'' and '' Human alphaherpesvirus 2'', are two members of the human ''Herpesviridae'' family, a set of viruses that produce viral inf ...

. It is available in a topical gel under trade names Viru-Merz and Viru-Merz Serol. Its performance is similar to aciclovir. Like rimantadine,

amantadine Amantadine, sold under the brand name Gocovri among others, is a medication used to treat dyskinesia associated with parkinsonism and influenza caused by type A influenzavirus, though its use for the latter is no longer recommended due to wid ...

, and

adapromine Adapromine is an antiviral drug of the adamantane group related to amantadine (1-aminoadamantane), rimantadine (1-(1-aminoethyl)adamantane), and memantine (1-amino-3,5-dimethyladamantane) that is marketed in Russia for the treatment and preventio ...

, tromantadine is a derivative of

adamantane Adamantane is an organic compound with a formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the m ...

Mechanism

Tromantadine inhibits the early and late events in the

virus A virus is a submicroscopic infectious agent that replicates only inside the living cells of an organism. Viruses infect all life forms, from animals and plants to microorganisms, including bacteria and archaea. Since Dmitri Ivanovsky's 1 ...

replication cycle. It changes the

glycoprotein Glycoproteins are proteins which contain oligosaccharide chains covalently attached to amino acid side-chains. The carbohydrate is attached to the protein in a cotranslational or posttranslational modification. This process is known as glycos ...

s of the host cells, therefore impeding the absorption of the virus. It inhibits penetration of the virus. It also prevents

uncoating A virus is a wikt:submicroscopic, submicroscopic infectious agent that replicates only inside the living Cell (biology), cells of an organism. Viruses infect all life forms, from animals and plants to microorganisms, including bacteria and ...

of the virions.

Synthesis

Amide formation between

and

chloroacetyl chloride Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical. Production Industrially, it is produced by the carbonylation of methylene chloride, oxidation of vinylidene chlorid ...

gives N-Adamantan-1-yl-2-chloro-acetamide 689-59-8(1). Ether formation with

Deanol Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care produ ...

(2) then completes the synthesis of tromantadine (3).

References

External links

Viru-Merz website
Anti-herpes virus drugs Adamantanes Acetamides Dimethylamino compounds {{dermatologic-drug-stub