Chemistry:Sorivudine

Short description: Chemical compound

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 Y
PubChem CID	5282192
ChemSpider	4445384 N
UNII	C7VOZ162LV
KEGG	D01734 Y
ChEMBL	ChEMBL375035 N
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 N Key:GCQYYIHYQMVWLT-HQNLTJAPSA-N N
NY (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.

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

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.

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.