Tromantadine: Difference between revisions

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Tromantadine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Topical
ATC code	D06BB02 (WHO) J05AC03 (WHO);
Identifiers
	IUPAC name N-1-adamantyl-N-[2-(dimethylamino)ethoxy]acetamide;
CAS Number	53783-83-8 ;
PubChem CID	64377;
ChemSpider	57947 ;
UNII	H191JFG8WA;
KEGG	D07199 ;
NIAID ChemDB	007760;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C16H28N2O2
Molar mass	280.406 g/mol
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 ;
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VisualWikitext

Latest revision as of 15:12, 10 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Tromantadine is an antiviral medicine used to treat herpes simplex virus. It is available in a topical gel under trade name Viru-Merz. Its performance is similar to aciclovir.

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

Mechanism

Tromantadine inhibits the early and late events in the virus replication cycle.^[1] 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.

References

↑ 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.

External links

Viru-Merz website

[pmid6297383-1] 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.

[1]

@@ Line 1: / Line 1: @@
-{{Drugbox|
+{{Drugbox
-|IUPAC_name = ''N''-1-adamantyl-''N''-[2-(dimethylamino)ethoxy]acetamide
+| Verifiedfields = changed
+| Watchedfields = changed
+| verifiedrevid = 470617884
+| IUPAC_name = ''N''-1-adamantyl-''N''-[2-(dimethylamino)ethoxy]acetamide
 | image = Tromantadine.png
-| CAS_number=53783-83-8
+| alt = Skeletal formula
-| ATC_prefix=D06
+| image2 = Tromantadine-3D-balls.png
-| ATC_suffix=BB02
+| alt2 = Ball-and-stick model
-| PubChem=64377
+<!--Clinical data-->
-| DrugBank=
+| tradename =
-| C = 16 |H = 28 |N = 2 |O = 2
+| Drugs.com = {{drugs.com|international|tromantadine}}
+| pregnancy_category =
+| legal_status =
+| routes_of_administration = [[Topical]]
+<!--Pharmacokinetic data-->
+| bioavailability =
+| metabolism =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 53783-83-8
+| ATC_prefix = D06
+| ATC_suffix = BB02
+| ATC_supplemental = {{ATC|J05|AC03}}
+| PubChem = 64377
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 57947
+| NIAID_ChemDB = 007760
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = H191JFG8WA
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D07199
+<!--Chemical data-->
+| C=16 | H=28 | N=2 | O=2
 | molecular_weight = 280.406 [[Gram|g]]/[[Mole (unit)|mol]]
-| smiles = O=C(C)N(OCCN(C)C)C23CC1CC(C3)CC(C2)C1
+| smiles = O=C(NC13CC2CC(CC(C1)C2)C3)COCCN(C)C
-| bioavailability=
+| 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)
-| metabolism =
+| InChIKey = UXQDWARBDDDTKG-UHFFFAOYAP
-| elimination_half-life=
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| excretion =
+| 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)
-| pregnancy_category =
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| legal_status =
+| StdInChIKey = UXQDWARBDDDTKG-UHFFFAOYSA-N
-| routes_of_administration= [[Topical]]
 }}
-'''Tromantadine''' is an [[antiviral]] [[medicine]] used to treat [[herpes simplex virus]]. It is available in a topical [[gel]] under trade name '''Viru-Merz'''. Its performance is similar to [[aciclovir]].
+              __NOTOC__
+{{SI}}
+{{CMG}}
-Tromantadine inhibits the early and late events in the [[virus]] replication cycle. 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.
+==Overview==
+'''Tromantadine''' is an antiviral medicine used to treat [[herpes simplex virus]]. It is available in a topical [[gel]] under trade name '''Viru-Merz'''. Its performance is similar to [[aciclovir]].
 Like [[rimantadine]] and [[amantadine]], tromantadine is a derivative of [[adamantane]].
+==Mechanism==
+Tromantadine inhibits the early and late events in the [[virus]] replication cycle.<ref name="pmid6297383">{{cite journal |author=Rosenthal KS, Sokol MS, Ingram RL, Subramanian R, Fort RC |title=Tromantadine: inhibitor of early and late events in herpes simplex virus replication |journal=Antimicrob. Agents Chemother. |volume=22 |issue=6 |pages=1031–6 |date=December 1982 |pmid=6297383 |pmc=185716 |doi= 10.1128/aac.22.6.1031|url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=6297383}}</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.
+==References==
+{{reflist|2}}
 ==External links==
 *[http://www.brookespharma.com/brands_virumerz_main.htm Viru-Merz website]
-{{antimicrobial-stub}}
 {{Antibiotics and chemotherapeutics for dermatological use}}
 {{Antivirals}}
-[[Category:Antivirals]]
+[[Category:Drug]]
+[[Category:Amines]]

v t e Antibiotics and chemotherapeutics for dermatological use (D06)
Antibiotics: tetracycline and derivatives	Demeclocycline - Chlortetracycline - Oxytetracycline - Tetracycline
Antibiotics: other	Fusidic acid - Chloramphenicol - Neomycin - Bacitracin - Gentamicin - Tyrothricin - Mupirocin - Nadifloxacin - Virginiamycin - Rifaximin - Amikacin
Chemotherapeutics: sulfonamides	Silver sulfadiazine - Sulfathiazole - Mafenide - Sulfamethizole - Sulfanilamide - Sulfamerazine
Chemotherapeutics: antivirals	Idoxuridine - Tromantadine - Aciclovir - Podophyllotoxin - Inosine - Penciclovir - Lysozyme - Ibacitabine - Edoxudine - Imiquimod - Docosanol
Chemotherapeutics: other	Metronidazole

v t e Antivirals, other than for HIV (primarily J05, also S01AD and D06BB)
Anti-herpesvirus (DNA, I)	guanine analogues (Aciclovir, Famciclovir, Ganciclovir, Penciclovir, Valaciclovir, Valganciclovir) • nucleoside analogues (Idoxuridine, Trifluridine, Vidarabine) • Cidofovir • Docosanol • Fomivirsen • Foscarnet • Tromantadine
HPV/MC (DNA, I)	Imiquimod • Podophyllotoxin
Hepatitis B (DNA, VII)	Adefovir • Interferon alfa-2b • Pegylated interferon alfa-2a • Entecavir • Lamivudine • Telbivudine • Tenofovir^†
Hepatitis C (RNA, IV)	Pegylated interferon alpha • Ribavirin • Taribavirin^† • Boceprevir^†
Picornavirus (RNA, IV)	Pleconaril^†
Anti-influenza agents (RNA, V)	Arbidol adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine) neuraminidase inhibitors (Oseltamivir, Zanamivir, Peramivir^†)
HIV (Reverse, VI)	See HIV pharm
Other antiviral agents	general (Inosine, Interferon)
^†Undergoing clinical trials, not FDA approved.

Clinical data


AHFS/Drugs.com	International Drug Names
Routes of administration	Topical
ATC code	D06BB02 (WHO) J05AC03 (WHO)
Identifiers
IUPAC name N-1-adamantyl-N-[2-(dimethylamino)ethoxy]acetamide
CAS Number	53783-83-8^N
PubChem CID	64377
ChemSpider	57947^Y
UNII	H191JFG8WA
KEGG	D07199^Y
NIAID ChemDB	007760
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₆H₂₈N₂O₂
Molar mass	280.406 g/mol
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)^Y Key:UXQDWARBDDDTKG-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)