| Revision as of 14:31, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{drugbox}} taken from revid 466409152 of page Tromantadine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 16:38, 12 October 2023 edit Boghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,946 edits consistent citation formatting |
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{{Short description|Antiviral medicine used to treat herpes simplex virus}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 447427025 |
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| Watchedfields = changed |
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| IUPAC_name = ''N''-1-adamantyl-''N''-acetamide |
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| verifiedrevid = 470617884 |
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| image = Tromantadine.png |
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| IUPAC_name = ''N''-(1-adamantyl)-2-acetamide |
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| image = Tromantadine.svg |
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| alt = Skeletal formula |
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| alt = Skeletal formula |
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| image2 = Tromantadine-3D-balls.png |
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| alt2 = Ball-and-stick model |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Viru-Merz |
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| Drugs.com = {{drugs.com|international|tromantadine}} |
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| Drugs.com = {{drugs.com|international|tromantadine}} |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_US = Not FDA-approved |
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| legal_status = |
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| legal_status = ] <small>(])</small> |
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| routes_of_administration = ] |
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| routes_of_administration = ] (]) |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 53783-83-8 --> |
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| CAS_number = 53783-83-8 |
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| ATC_prefix = D06 |
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| ATC_prefix = D06 |
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| ATC_suffix = BB02 |
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| ATC_suffix = BB02 |
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| ATC_supplemental = {{ATC|J05|AC03}} |
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| PubChem = 64377 |
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| PubChem = 64377 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 57947 |
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| ChemSpiderID = 57947 |
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| NIAID_ChemDB = 007760 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = H191JFG8WA |
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| UNII = H191JFG8WA |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07199 |
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| KEGG = D07199 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=16 | H=28 | N=2 | O=2 |
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| C=16 | H=28 | N=2 | O=2 |
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| SMILES = O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C |
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| molecular_weight = 280.406 ]/] |
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| smiles = O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C |
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| InChI = 1/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) |
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| InChIKey = UXQDWARBDDDTKG-UHFFFAOYAP |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey = UXQDWARBDDDTKG-UHFFFAOYSA-N |
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| StdInChIKey = UXQDWARBDDDTKG-UHFFFAOYSA-N |
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}} |
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}} |
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'''Tromantadine''' is an ] used to treat ]. It is available in a ] under trade names '''Viru-Merz''' and '''Viru-Merz Serol'''. Its performance is similar to ].<ref>{{cite journal | vauthors = Ostheimer KE, Busch T, Görtelmeyer R, Hahn KD | title = Randomized double-blind trial of tromantadine versus aciclovir in recurrent herpes orofacialis | journal = Arzneimittel-Forschung | volume = 39 | issue = 9 | pages = 1152–1155 | date = September 1989 | pmid = 2686658 }}</ref><ref>{{cite journal | vauthors = Diezel W, Michel G, Görtelmeyer R, Ostheimer KE | title = Efficacy of tromantadine and aciclovir in the topical treatment of recurrent herpes orofacialis. Comparison in a clinical trial | journal = Arzneimittel-Forschung | volume = 43 | issue = 4 | pages = 491–496 | date = April 1993 | pmid = 8494582 }}</ref> |
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Like ], ], and ], tromantadine is a derivative of ]. |
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==Mechanism== |
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Tromantadine inhibits the early and late events in the ] replication cycle.<ref name="pmid6297383">{{cite journal | vauthors = Rosenthal KS, Sokol MS, Ingram RL, Subramanian R, Fort RC | title = Tromantadine: inhibitor of early and late events in herpes simplex virus replication | journal = Antimicrobial Agents and Chemotherapy | volume = 22 | issue = 6 | pages = 1031–1036 | date = December 1982 | pmid = 6297383 | pmc = 185716 | doi = 10.1128/aac.22.6.1031 }}</ref> It changes the ]s of the host cells, therefore impeding the absorption of the virus. It inhibits penetration of the virus. It also prevents ] of the ]s.{{cn|date=November 2022}} |
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== References == |
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{{Reflist|2}} |
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== External links == |
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* |
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{{Antibiotics and chemotherapeutics for dermatological use}} |
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{{Antivirals}} |
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] |
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] |
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] |
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{{antiinfective-drug-stub}} |
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{{dermatologic-drug-stub}} |