Sorivudine

Sorivudine (INN), is a nucleoside analogue antiviral drug, marketed under trade names such as Usevir (Nippon Shoji, Eisai) and Brovavir (BMS).

Sorivudine

Clinical data
Trade names	Usevir, Brovavir
Other names	BV-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
IUPAC name 1-β-D-arabinofuranosyl-5-[(E)-2-bromovinyl]pyrimidine-2,4(1H,3H)-dione
CAS Number	77181-69-2
PubChem CID	5282192
ChemSpider	4445384
UNII	C7VOZ162LV
KEGG	D01734
ChEMBL	ChEMBL375035
CompTox Dashboard (EPA)	DTXSID6057827
Chemical and physical data
Formula	C11H13BrN2O6
Molar mass	349.137 g·mol^−1
3D model (JSmol)	Interactive image
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 Key:GCQYYIHYQMVWLT-HQNLTJAPSA-N
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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.

• Herpes simplex virus type I (HSV-1)
• Varicella zoster virus (VZV)
• Epstein-Barr virus (EBV)

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.[1]

Bromovinyluracil (BVU)

References

1. "UAW – Aus Fehlern lernen - Potenziell tödlich verlaufende Wechselwirkung zwischen Brivudin (Zostex) und 5-Fluoropyrimidinen" (PDF). Deutsches Ärzteblatt (in German). 103 (27). 7 July 2006.