Sorivudine

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]

Sorivudine
Clinical data
Trade namesUsevir, 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
MetabolismViral thymidine kinase
ExcretionKidney
Identifiers
IUPAC name
  • 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
FormulaC11H13BrN2O6
Molar mass349.137 g·mol−1
3D model (JSmol)
SMILES
  • c1c(c(=O)[nH]c(=O)n1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)/C=C/Br
InChI
  • 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 N
  • Key:GCQYYIHYQMVWLT-HQNLTJAPSA-N N
 NY (what is this?)  (verify)

Pharmacology

Feature
  • First-line treatment of herpes drug acyclovir was (Zovirax, Activir) from VZV strong activity of the virus.
  • Undergoes gastrointestinal absorption, absorption from the gastrointestinal tract after the most degrading without being excreted in urine.

Mechanism of action
  • 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 grow.

Microbiology

Sorivudine is active against most species in the herpesvirus family.

Interactions

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]

Bromovinyluracil (BVU)

References
  1. Whitley RJ (1996). "Sorivudine: a potent inhibitor of varicella zoster virus replication". Advances in Experimental Medicine and Biology. 394: 41–4. doi:10.1007/978-1-4757-9209-6_5. 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.


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