Tromantadine

Tromantadine
Clinical data
Trade names	Viru-Merz
AHFS/Drugs.com	International Drug Names
Routes of; administration	Topical (gel)
ATC code	D06BB02 (WHO) J05AC03 (WHO);
Legal status
Legal status	US: Not FDA-approved ; OTC (RU);
Identifiers
	IUPAC name N-(1-adamantyl)-2-[2-(dimethylamino)ethoxy]acetamide;
CAS Number	53783-83-8 ;
PubChem CID	64377;
ChemSpider	57947 ;
UNII	H191JFG8WA;
KEGG	D07199 ;
NIAID ChemDB	007760;
CompTox Dashboard (EPA)	DTXSID00202062 ;
ECHA InfoCard	100.053.409
Chemical and physical data
Formula	C16H28N2O2
Molar mass	280.412 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:UXQDWARBDDDTKG-UHFFFAOYSA-N ;
	(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.^[1]^[2]

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

Mechanism[edit]

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.^{[citation needed]}

Synthesis[edit]

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[edit]

^ 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.
^ 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.
^ 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.
^ 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.
^ May G, Peteri D. [Synthesis and antiviral effects of adamantan derivatives]. Arzneimittelforschung. 1973;23(5):718-21. PMID: 4351043.
^ DE1941218 idem Dezso Peteri, Arthur Scherm, U.S. Patent 3,705,194 (1971 to Merz & Co).
^ 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.

External links[edit]

Viru-Merz website

This antiinfective drug article is a stub. You can help Wikipedia by expanding it.

This dermatologic drug article is a stub. You can help Wikipedia by expanding it.

[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.

[pmid6297383-3] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]