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Latest revision as of 19:15, 11 March 2024 edit undo172.221.160.24 (talk) →Mechanism of action: Viruses don't "grow", they duplicate themselves |
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{{Short description|Chemical compound}} |
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{{drugbox | |
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{{refimprove|date=March 2015}} |
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{{Drugbox |
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| verifiedrevid = 409575914 |
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| IUPAC_name = 1-β-<small>D</small>-arabinofuranosyl-5-pyrimidine-2,4(1''H'',3''H'')-dione |
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| IUPAC_name = 1-β-<small>D</small>-arabinofuranosyl-5-pyrimidine-2,4(1''H'',3''H'')-dione |
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| image = Sorivudin.svg |
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| image = Sorivudine.svg |
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| synonyms = <small>BV-araU, Bromovinyl araU, 5-Bromovinyl-araU, 5--1-pyrimidine-2,4-dione</small> |
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<!--Clinical data--> |
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| tradename = Usevir, Brovavir |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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| metabolism = Viral thymidine kinase |
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| excretion = ] |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 77181-69-2 |
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| CAS_number = 77181-69-2 |
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| ATC_prefix = J05 |
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| ATC_prefix = none |
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| ATC_suffix = AB15 |
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| ATC_suffix = |
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| ATC_supplemental = |
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| PubChem = 5282192 |
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| PubChem = 5282192 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = C7VOZ162LV |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D01734 |
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| KEGG = D01734 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 375035 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4445384 |
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<!--Chemical data--> |
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| C=11 | H=13 | Br=1 | N=2 | O=6 |
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| C=11 | H=13 | Br=1 | N=2 | O=6 |
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| synonyms = <small>BV-araU, Bromovinyl araU, 5-Bromovinyl-araU, 5--1-pyrimidine-2,4-dione</small> |
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| molecular_weight = 349.14 g/mol |
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| smiles = c1c(c(=O)c(=O)n12(((O2)CO)O)O)/C=C/Br |
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| melting_point = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| bioavailability = |
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| StdInChI = 1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1 |
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| protein_bound = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| metabolism = Viral thymidine kinase |
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| StdInChIKey = GCQYYIHYQMVWLT-HQNLTJAPSA-N |
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| elimination_half-life = |
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| excretion = ] |
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| pregnancy_category = |
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| legal_status = |
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| routes_of_administration = oral |
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'''Sorivudine''' (]) chemical name '''(E)-5-(2-Bromovinyl)- 1β-D-arabinofuranosyluracil''', is a ] ], marketed under trade names such as '''Usevir''' (], ]) and '''Brovavir''' (]). |
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'''Sorivudine''' (]), is a ] ], marketed under trade names such as '''Usevir''' (], ]) and '''Brovavir''' (]). It is used for the treatment of ] virus infections.<ref name="pmid8815706">{{cite book | vauthors = Whitley RJ | title = Antiviral Chemotherapy 4 | chapter = Sorivudine: A Potent Inhibitor of Varicella Zoster Virus Replication | series = Advances in Experimental Medicine and Biology | volume = 394 | pages = 41–4 | date = 1996 | pmid = 8815706 | doi = 10.1007/978-1-4757-9209-6_5 | isbn = 978-1-4757-9211-9 | chapter-url = }}</ref> |
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==Pharmacology== |
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==Pharmacology== |
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===Feature=== |
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===Feature=== |
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*First-line treatment of herpes drug acyclovir was (Zovirax, Activir) from VZV strong activity of the virus. |
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* First-line{{fact|date=February 2016}} treatment of herpes drug acyclovir was (Zovirax, Activir) from VZV strong activity of the virus. |
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*Superior gastrointestinal absorption, absorption from the gastrointestinal tract after the most degrading without being excreted as urine. |
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* Undergoes gastrointestinal absorption, absorption from the gastrointestinal tract after the most degrading without being excreted in urine. |
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===Mechanism of action=== |
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===Mechanism of action=== |
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*Sorivudine is phosphorylated by thymidine kinase activity in the body and is absorbed into the virus's DNA, to inhibit viral DNA replication of DNA polymerase to make it fail to inhibit viral growth. |
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* Sorivudine is phosphorylated by thymidine kinase activity in the body and is absorbed into the virus's DNA instead of the correct nucleoside. It is a competitive inhibitor of DNA polymerase, so the viral DNA cannot be replicated and the virus cannot replicate. |
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===Microbiology=== |
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===Microbiology=== |
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Sorivudine is active against most species in the ] family. |
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Sorivudine is active against most species in the ] family. |
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*] type I (HSV-1) |
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* ] type I (HSV-1) |
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*] (VZV) |
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* ] (VZV) |
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*] (EBV) |
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* ] (EBV) |
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==Interactions== |
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{{Antivirals}} |
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] |
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Sorivudine interacts strongly and in some cases lethally with ] (5-FU), its ]s and related substances. This is based on the ] bromovinyluracil (BVU), which irreversibly inhibits the enzyme ] (DPD) which is necessary for inactivating 5-FU. The closely related drug ] has the same interaction.<ref>{{cite journal|url=http://www.akdae.de/Arzneimittelsicherheit/Bekanntgaben/Archiv/2006/764-200607071.pdf|title=UAW – Aus Fehlern lernen - Potenziell tödlich verlaufende Wechselwirkung zwischen Brivudin (Zostex) und 5-Fluoropyrimidinen|journal=Deutsches Ärzteblatt|volume=103|issue=27|date=7 July 2006|language=de}}</ref> |
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{{Pharm-stub|Sorivudine}} |
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{{clear}} |
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{{Medical-stub|Sorivudine}} |
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Also, it should be taken into consideration that the ability to metabolize this drug can decrease with age due to the composition of the ]. Specifically, after the age of 60, it has been observed a reduction of the metabolic potential to degrade this compound decreases. <ref>{{cite journal|url=https://www.nature.com/articles/s41587-022-01628-0|title=Genome-scale metabolic reconstruction of 7,302 human microorganisms for personalized medicine|display-authors=3|vauthors=Heinken A, Hertel J, Acharya G, Ravcheev DA, Nyga M, Okpala OE, Hogan M, Magnúsdóttir S, Martinelli F, Nap B, Preciat G, Edirisinghe JN, Henry CS, Fleming RM, Thiele |journal=Nature Biotechnology|volume=41|issue=9|pages=1320–1331|date=19 January 2023|doi=10.1038/s41587-022-01628-0 |language=english|pmc=10497413}}</ref> |
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==References== |
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{{reflist}} |
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{{Antiinfective-drug-stub}} |
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{{Antiinfective-drug-stub}} |
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