Sorivudine

Sorivudine
Clinical data

Trade names	Usevir, Brovavir
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
Synonyms	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
CAS Number	77181-69-2^Y
PubChem (CID)	5282192
ChemSpider	4445384^N
UNII	C7VOZ162LV^N
KEGG	D01734^Y
ChEMBL	CHEMBL375035^N
Chemical and physical data
Formula	C₁₁H₁₃BrN₂O₆
Molar mass	349.14 g/mol
3D model (Jmol)	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^N Key:GCQYYIHYQMVWLT-HQNLTJAPSA-N^N
^NY (what is this?) (verify)

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

Pharmacology

Feature

First-line treatment of herpes drug acyclovir was (Zovirax, Activir) from VZV strong activity of the virus.
Superior gastrointestinal absorption, absorption from the gastrointestinal tract after the most degrading without being excreted as 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.^[1]

Bromovinyluracil (BVU)

References

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

DNA virus antivirals (primarily J05, also S01AD and D06BB)

Baltimore I

Herpesvirus

DNA-synthesis
inhibitor

TK activated

Purine analogue	guanine (Aciclovir^#/Valaciclovir Ganciclovir/Valganciclovir Penciclovir/Famciclovir) adenine (Vidarabine)

Pyrimidine analogue	uridine (Idoxuridine Trifluridine (+tipiracil) Edoxudine) thymine Brivudine Sorivudine cytosine (Cytarabine)

Not TK activated

Foscarnet

Other

HPV/MC

Vaccinia

assembly: Rifampicin

Poxviridae

Methisazone

Hepatitis B (VII)

Multiple/general

Nucleic acid inhibitors	Cidofovir

Interferon	Interferon alfa 2b Peginterferon alfa-2a

Multiple/unknown	Ribavirin^#/Taribavirin^† Moroxydine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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