Brivudine

Brivudine

Clinical data
Trade names	Zostex, Mevir, Brivir, many others
Other names	BVDU
AHFS/Drugs.com	International Drug Names
Pregnancy category	Contraindicated
Routes of administration	Oral
ATC code	J05AB15 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	30%
Protein binding	>95%
Metabolism	Thymidine phosphorylase
Metabolites	Bromovinyluracil
Elimination half-life	16 hours
Excretion	65% renal (mainly metabolites), 20% faeces
Identifiers
IUPAC name 5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number	69304-47-8 N
PubChem CID	446727
ChemSpider	394011 Y
UNII	2M3055079H
KEGG	D07249 N
ChEBI	CHEBI:47278
ChEMBL	ChEMBL31634 Y
CompTox Dashboard (EPA)	DTXSID0045755
Chemical and physical data
Formula	C11H13BrN2O5
Molar mass	333.138 g·mol−1
3D model (JSmol)	Interactive image
Specific rotation	+9°±1°
Density	1.86 g/cm3
Melting point	165 to 166 °C (329 to 331 °F) (decomposes)
SMILES Br[C@H]=CC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)C2)CO
InChI InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1 Y Key:ODZBBRURCPAEIQ-PIXDULNESA-N Y
NY (what is this?)  (verify)

Brivudine (trade names Zostex, Mevir, Brivir, among others) is an antiviral drug used in the treatment of herpes zoster ("shingles"). Like other antivirals, it acts by inhibiting replication of the target virus.