Sorivudine

Last updated
Sorivudine
Sorivudine.svg
Clinical data
Trade names Usevir, Brovavir
Other namesBV-araU, Bromovinyl araU, 5-Bromovinyl-araU, 5-[(E)-2-bromoethenyl]-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Routes of
administration
Oral
ATC code
  • none
Pharmacokinetic data
Metabolism Viral thymidine kinase
Excretion Kidney
Identifiers
  • 1-β-D-arabinofuranosyl-5-[(E)-2-bromovinyl]pyrimidine-2,4(1H,3H)-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H13BrN2O6
Molar mass 349.137 g·mol−1
3D model (JSmol)
  • c1c(c(=O)[nH]c(=O)n1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)/C=C/Br
  • InChI=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 X mark.svgN
  • Key:GCQYYIHYQMVWLT-HQNLTJAPSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Sorivudine (INN), is a nucleoside analogue antiviral drug, marketed under trade names such as Usevir (Nippon Shoji, Eisai) and Brovavir (BMS). It is used for the treatment of varicella zoster virus infections. [1]

Contents

Pharmacology

Feature

Mechanism of action

Microbiology

Sorivudine is active against most species in the herpesvirus family.

Interactions

Bromovinyluracil (BVU) Bromovinyluracil skeletal.svg
Bromovinyluracil (BVU)

Sorivudine interacts strongly and in some cases lethally with fluorouracil (5-FU), its prodrugs and related substances. This is based on the metabolite bromovinyluracil (BVU), which irreversibly inhibits the enzyme dihydropyrimidine dehydrogenase (DPD) which is necessary for inactivating 5-FU. The closely related drug brivudine has the same interaction. [2]

Also, it should be taken into consideration that the ability to metabolize this drug can decrease with age due to the composition of the gut microbiota. Specifically, after the age of 60, it has been observed a reduction of the metabolic potential to degrade this compound decreases. [3]

Related Research Articles

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Varicella zoster virus (VZV), also known as human herpesvirus 3 or Human alphaherpesvirus 3 (taxonomically), is one of nine known herpes viruses that can infect humans. It causes chickenpox (varicella) commonly affecting children and young adults, and shingles in adults but rarely in children. VZV infections are species-specific to humans. The virus can survive in external environments for a few hours.

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References

  1. Whitley RJ (1996). "Sorivudine: A Potent Inhibitor of Varicella Zoster Virus Replication". Antiviral Chemotherapy 4. Advances in Experimental Medicine and Biology. Vol. 394. pp. 41–4. doi:10.1007/978-1-4757-9209-6_5. ISBN   978-1-4757-9211-9. PMID   8815706.
  2. "UAW – Aus Fehlern lernen - Potenziell tödlich verlaufende Wechselwirkung zwischen Brivudin (Zostex) und 5-Fluoropyrimidinen" (PDF). Deutsches Ärzteblatt (in German). 103 (27). 7 July 2006.
  3. Heinken A, Hertel J, Acharya G, et al. (19 January 2023). "Genome-scale metabolic reconstruction of 7,302 human microorganisms for personalized medicine". Nature Biotechnology. 41 (9): 1320–1331. doi:10.1038/s41587-022-01628-0. PMC   10497413 .