Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tromantadine: Difference between pages

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Saving copy of the {{drugbox}} taken from revid 466409152 of page Tromantadine for the Chem/Drugbox validation project (updated: 'CAS_number').
 
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{{Short description|Antiviral medicine used to treat herpes simplex virus}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Tromantadine|oldid=466409152}} 466409152] of page [[Tromantadine]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| verifiedrevid = 447427025
| Watchedfields = changed
⚫
| IUPAC_name = ''N''-1-adamantyl-''N''-[2-(dimethylamino)ethoxy]acetamide
⚫
| verifiedrevid = 470617884
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| image = Tromantadine.png
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| IUPAC_name = ''N''-(1-adamantyl)-2-[2-(dimethylamino)ethoxy]acetamide
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| image = Tromantadine.svg
| alt = Skeletal formula
| alt = Skeletal formula
| image2 = Tromantadine-3D-balls.png
| alt2 = Ball-and-stick model
<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename = Viru-Merz
| Drugs.com = {{drugs.com|international|tromantadine}}
| Drugs.com = {{drugs.com|international|tromantadine}}
| pregnancy_category =
| pregnancy_category =
| legal_US = Not FDA-approved
| legal_status =
| legal_status = [[Over-the-counter drug|OTC]] <small>([[Russia|RU]])</small>
| routes_of_administration = [[Topical]]
| routes_of_administration = [[Topical]] ([[gel]])

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| metabolism =
| metabolism =
| excretion =
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 53783-83-8 -->
| CAS_number = 53783-83-8
| ATC_prefix = D06
| ATC_prefix = D06
| ATC_suffix = BB02
| ATC_suffix = BB02
| ATC_supplemental = {{ATC|J05|AC03}}
| PubChem = 64377
| PubChem = 64377
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 57947
| ChemSpiderID = 57947
| NIAID_ChemDB = 007760
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H191JFG8WA
| UNII = H191JFG8WA
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07199
| KEGG = D07199

<!--Chemical data-->
<!--Chemical data-->
| C=16 | H=28 | N=2 | O=2
| C=16 | H=28 | N=2 | O=2
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| SMILES = O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C
| molecular_weight = 280.406 [[Gram|g]]/[[Mole (unit)|mol]]
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| smiles = O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C
| 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)
| InChIKey = UXQDWARBDDDTKG-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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)
| 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
| StdInChIKey = UXQDWARBDDDTKG-UHFFFAOYSA-N
}}
}}

'''Tromantadine''' is an [[antiviral medicine]] used to treat [[herpes simplex virus]]. It is available in a [[Topical gels|topical gel]] under trade names '''Viru-Merz''' and '''Viru-Merz Serol'''. Its performance is similar to [[aciclovir]].<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>

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

==Mechanism==
Tromantadine inhibits the early and late events in the [[virus]] 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 [[glycoprotein]]s of the host cells, therefore impeding the absorption of the virus. It inhibits penetration of the virus. It also prevents [[uncoating]] of the [[virion]]s.{{cn|date=November 2022}}

== References ==
{{Reflist|2}}

== External links ==
* [https://web.archive.org/web/20050429203941/http://www.brookespharma.com/brands_virumerz_main.htm Viru-Merz website]

{{Antibiotics and chemotherapeutics for dermatological use}}
{{Antivirals}}

[[Category:Anti-herpes virus drugs]]
[[Category:Adamantanes]]
[[Category:Acetamides]]
[[Category:Dimethylamino compounds]]

{{antiinfective-drug-stub}}
{{dermatologic-drug-stub}}
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