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Antiinfective agent stubs
Tromantadine
Другие языки:

Tromantadine

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Tromantadine
Skeletal formula
Clinical data
Trade names Viru-Merz
AHFS/Drugs.com International Drug Names
Routes of
administration		 Topical (gel)
ATC code
Legal status
Legal status
  • US: Not FDA-approved
  • OTC (RU)
Identifiers
  • N-(1-adamantyl)-2-[2-(dimethylamino)ethoxy]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard 100.053.409
Chemical and physical data
Formula C16H28N2O2
Molar mass 280.412 g·mol−1
3D model (JSmol)
  • O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C
  • InChI=1S/C16H28N2O2/c1-18(2)3-4-20-11-15(19)17-16-8-12-5-13(9-16)7-14(6-12)10-16/h12-14H,3-11H2,1-2H3,(H,17,19) checkY
  • Key:UXQDWARBDDDTKG-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tromantadine is an antiviral medicine used to treat herpes simplex virus. 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, and adapromine, tromantadine is a derivative of adamantane.

Mechanism

Tromantadine inhibits the early and late events in the virus replication cycle. It changes the glycoproteins of the host cells, therefore impeding the absorption of the virus. It inhibits penetration of the virus. It also prevents uncoating of the virions.

Synthesis

Synthesis: Patents:

Amide formation between amantadine and chloroacetyl chloride gives N-Adamantan-1-yl-2-chloro-acetamide [5689-59-8] (1). Ether formation with Deanol (2) then completes the synthesis of tromantadine (3).

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