Tromantadine

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.[1][2]

Tromantadine
Clinical data
Trade namesViru-Merz
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Topical (gel)
ATC code
Legal status
Legal status
  • US: Not FDA-approved
  • OTC (RU)
Identifiers
IUPAC name
  • N-(1-adamantyl)-2-[2-(dimethylamino)ethoxy]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.053.409
Chemical and physical data
FormulaC16H28N2O2
Molar mass280.412 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C
InChI
  • 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) Y
  • Key:UXQDWARBDDDTKG-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Like rimantadine, amantadine, and adapromine, tromantadine is a derivative of adamantane.

Mechanism

Tromantadine inhibits the early and late events in the virus replication cycle.[3] 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:[4][5] Patents:[6][7]

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).

References
  1. Ostheimer, K. E.; Busch, T.; Görtelmeyer, R.; Hahn, K. D. (September 1989). "Randomized double-blind trial of tromantadine versus aciclovir in recurrent herpes orofacialis". Arzneimittel-Forschung. 39 (9): 1152–1155. ISSN 0004-4172. PMID 2686658.
  2. Diezel, W.; Michel, G.; Görtelmeyer, R.; Ostheimer, K. E. (April 1993). "Efficacy of tromantadine and aciclovir in the topical treatment of recurrent herpes orofacialis. Comparison in a clinical trial". Arzneimittel-Forschung. 43 (4): 491–496. ISSN 0004-4172. PMID 8494582.
  3. Rosenthal KS, Sokol MS, Ingram RL, Subramanian R, Fort RC (December 1982). "Tromantadine: inhibitor of early and late events in herpes simplex virus replication". Antimicrob. Agents Chemother. 22 (6): 1031–6. doi:10.1128/aac.22.6.1031. PMC 185716. PMID 6297383.
  4. Peteri D, Sterner W. [Chemistry and toxicology of a new antiviral agent: N-(1-adamantyl)-2-(2-dimethylamino-ethoxy)-acetamide-HCl.1]. Arzneimittelforschung. 1973;23(4):577-81. PMID: 4740238.
  5. May G, Peteri D. [Synthesis and antiviral effects of adamantan derivatives]. Arzneimittelforschung. 1973;23(5):718-21. PMID: 4351043.
  6. DE1941218 idem Dezso Peteri, Arthur Scherm, U.S. Patent 3,705,194 (1971 to Merz & Co).
  7. U.S. Patent 20,140,045,779 idem Lifeng Xu, 徐利锋, WO 2012145981 (2014 to Liaoning Lifeng Scientific & Technology Development Company Ltd., 1 More ») Ex 18.


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