Brivudine: Difference between revisions

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Brivudine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	exclusion;
Routes of; administration	oral
ATC code	J05AB15 (WHO) ;
Pharmacokinetic data
Bioavailability	30%
Elimination half-life	16 hours
Excretion	mainly renal
Identifiers
	IUPAC name 5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione;
CAS Number	69304-47-8 ;
PubChem CID	446727;
ChemSpider	394011 ;
UNII	2M3055079H;
ChEMBL	ChEMBL31634 ;
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	C11H13BrN2O5
Molar mass	333.135 g/mol
3D model (JSmol)	Interactive image;
	SMILES Br[C@H]=CC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)C2)CO;
	InChI InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1 ; Key:ODZBBRURCPAEIQ-PIXDULNESA-N ;
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VisualWikitext

Latest revision as of 20:42, 12 April 2015

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

Overview

Brivudine is an antiviral drug used in the treatment of herpes zoster.

History

Brivudine is a similar drug to acyclovir^{[clarification needed]}. The compound was first synthesized by scientists at the University of Birmingham in the UK in the 1970s. It was shown to be a potent inhibitor of the herpes simplex virus Type 1 (HSV-1) as well as the varicella zoster virus (VZV) by Erik De Clercq at the Rega Institute for Medical Research in Belgium in 1979. In the 1980s the drug became commercially available in East Germany, where it was marketed as Helpin by a pharmaceutical company called Berlin-Chemie.

Approvals

Brivudine is approved for use in Germany and other European countries including Italy.

Mechanism of Action

Brivudine is an analogue of the nucleoside thymidine. The drug works because it is able to be incorporated into the viral DNA, but then blocks the action of DNA polymerases, thus inhibiting viral replication. The active compound is the 5'-triphosphate of BVDU, which is formed in subsequent phosphorylations by viral thymidine kinase and presumably by nucleoside diphosphate kinase.

Research

A Cochrane Systematic Review examined the effectiveness of multiple antiviral drugs in the treatment of herpes simplex virus epithelial keratitis. Brivudine was found to be significantly more effective than idoxuridine in increasing the number of successfully healed eyes of participants.^[1]

The drug's name

Brivudine derives from the drug's chemical name of bromovinyldeoxyuridine or BVDU for short. The drug's full chemical description is (E)-5-(2-bromovinyl)-2-deoxyuridine. It is also sold as Bridic, Brivox, Brivudin, Helpin, Zerpex, Zonavir and Zostex.

Suppliers

Brivudine main supplier is Berlin-Chemie, now part of Italy's Menarini Group. The drug is approved for sale in Austria, Belgium, Germany, Greece, Italy, Luxembourg, Portugal and Spain. In Central America is provided Menarini Centro America and Wyeth.

References

↑ Wilhelmus KR (2010). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev. 12: CD002898. doi:10.1002/14651858.CD002898.pub4. PMID 21154352.

[Wilhelmus-1] Wilhelmus KR (2010). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev. 12: CD002898. doi:10.1002/14651858.CD002898.pub4. PMID 21154352.

[1]

@@ Line 1: / Line 1: @@
-{{Drugbox|
-|IUPAC_name = 5-[(''E'')-2-bromoethenyl]-1-[(2''R'',4''S'',5''R'')-4-hydroxy-<br>5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
+{{Drugbox
-| image=Brivudine.svg
+| Verifiedfields = changed
-| CAS_number=69304-47-8
+| verifiedrevid = 459982797
-| ATC_prefix=J05
+| IUPAC_name = 5-[(''E'')-2-bromoethenyl]-1-[(2''R'',4''S'',5''R'')-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
-| ATC_suffix=AB15
+| image = Brivudine.png
-| PubChem=446727
-| DrugBank=
+<!--Clinical data-->
-| C = 11 | H = 13 | Br = 1 | N = 2 | O = 5
+| tradename =
+| Drugs.com = {{drugs.com|international|brivudine}}
+| pregnancy_category = exclusion
+| legal_status =
+| routes_of_administration = oral
+<!--Pharmacokinetic data-->
+| bioavailability = 30%
+| metabolism =
+| elimination_half-life = 16 hours
+| excretion = mainly renal
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 69304-47-8
+| ATC_prefix = J05
+| ATC_suffix = AB15
+| PubChem = 446727
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 394011
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 2M3055079H
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 31634
+<!--Chemical data-->
+| C=11 | H=13 | Br=1 | N=2 | O=5
 | molecular_weight = 333.135 g/mol
-| bioavailability= 30%
+| smiles = Br[C@H]=CC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)C2)CO
-| metabolism =
+| InChI = 1/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
-| elimination_half-life= 16 hours
+| InChIKey = ODZBBRURCPAEIQ-PIXDULNEBW
-| excretion =  mainly renal
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| pregnancy_category = exclusion
+| StdInChI = 1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
-| legal_status =
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| routes_of_administration= oral
+| StdInChIKey = ODZBBRURCPAEIQ-PIXDULNESA-N
 }}
+              __NOTOC__
+{{SI}}
+{{CMG}}
+==Overview==
 '''Brivudine''' is an [[antiviral drug]] used in the treatment of [[herpes zoster]].
 ==History==
-Brivudine is a similar drug to [[acyclovir]]. The compound was first synthesized by scientists at the [[University of Birmingham]] in the UK in the 1970s. It was shown to be a potent inhibitor of the [[herpes simplex virus]] Type 1 (HSV-1) as well as the [[varicella zoster virus]] (VZV) by Erik De Clercq at the [[Rega Institute for Medical Research]] in [[Belgium]] in 1979. In the 1980s the drug became commercially available in [[East Germany]], where it was marketed as '''Helpin''' by a pharmaceutical company called Berlin-Chemie.
+Brivudine is a similar drug to [[acyclovir]]{{Clarify|date=July 2009}}. The compound was first synthesized by scientists at the [[University of Birmingham]] in the UK in the 1970s. It was shown to be a potent inhibitor of the [[herpes simplex virus]] Type 1 (HSV-1) as well as the [[varicella zoster virus]] (VZV) by [[Erik De Clercq]] at the [[Rega Institute for Medical Research]] in [[Belgium]] in 1979. In the 1980s the drug became commercially available in [[East Germany]], where it was marketed as '''Helpin''' by a pharmaceutical company called Berlin-Chemie.
 ==Approvals==
@@ Line 26: / Line 59: @@
 ==Mechanism of Action==
-Brivudine is an analogue of the [[nucleoside]] [[thymidine]]. The drug works because it is able to be incorporated into the viral DNA, but then blocks the action of DNA [[polymerases]], thus inhibiting viral replication.
+Brivudine is an analogue of the [[nucleoside]] [[thymidine]]. The drug works because it is able to be incorporated into the viral DNA, but then blocks the action of DNA [[polymerases]], thus inhibiting viral replication. The active compound is the 5'-triphosphate of BVDU, which is formed in subsequent phosphorylations by viral thymidine kinase and presumably by nucleoside diphosphate kinase.
+==Research==
+A [[Cochrane Collaboration|Cochrane Systematic Review]] examined the effectiveness of multiple antiviral drugs in the treatment of [[herpes of the eye|herpes simplex virus epithelial keratitis]]. Brivudine was found to be significantly more effective than [[idoxuridine]] in increasing the number of successfully healed eyes of participants.<ref name="Wilhelmus">{{cite journal |author= Wilhelmus KR |title= Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis |journal=Cochrane Database Syst Rev|volume=12 |pages= CD002898 |date=2010 |pmid= 21154352|doi= 10.1002/14651858.CD002898.pub4}}</ref>
 ==The drug's name==
-Brivudine derives from the drug's chemical name of bromovinyldeoxyuridine or BVDU for short. The drug's full chemical description is (E)-5-(2-bromovinyl)-2-deoxyuridine. It is also sold as Brivudin, Helpin, Zerpex, Zonavir and Zostex.
+Brivudine derives from the drug's chemical name of bromovinyldeoxyuridine or BVDU for short. The drug's full chemical description is (E)-5-(2-bromovinyl)-2-deoxyuridine. It is also sold as Bridic, Brivox, Brivudin, Helpin, Zerpex, Zonavir and Zostex.
 ==Suppliers==
-Brivudine main supplier is Berlin-Chemie, now part of Italy's Menarini Group. The drug is approved for sale in Austria, Belgium, Germany, Greece, Italy, Luxembourg and Spain.
+Brivudine main supplier is Berlin-Chemie, now part of Italy's Menarini Group. The drug is approved for sale in Austria, Belgium, Germany, Greece, Italy, Luxembourg, Portugal and Spain.  In Central America is provided Menarini Centro America and Wyeth.
-[[Category:Antivirals]]
+==References==
+{{reflist|2}}
 {{Antivirals}}
-{{antimicrobial-stub}}
-[[de:Brivudin]]
+[[Category:Nucleosides]]
-{{WikiDoc Help Menu}}
+[[Category:Drug]]
+[[Category:Organobromides]]

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
Pregnancy category	exclusion
Routes of administration	oral
ATC code	J05AB15 (WHO)
Pharmacokinetic data
Bioavailability	30%
Elimination half-life	16 hours
Excretion	mainly renal
Identifiers
IUPAC name 5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number	69304-47-8^N
PubChem CID	446727
ChemSpider	394011^Y
UNII	2M3055079H
ChEMBL	ChEMBL31634^Y
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	C₁₁H₁₃BrN₂O₅
Molar mass	333.135 g/mol
3D model (JSmol)	Interactive image
SMILES Br[C@H]=CC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)C2)CO
InChI InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1^Y Key:ODZBBRURCPAEIQ-PIXDULNESA-N^Y
^NY (what is this?) (verify)