brivudine

CHEBI:47278 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pyrimidine 2'-deoxyribonucleoside that is 2'-deoxyuridine in which the hydrogen at position 5 of the uracil ring is substituted by a 2-bromoethenyl group. It is an antiviral drug used for the treatment of herpes zoster (shingles). — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:19255 CHEBI:19255
CHEBI:37141 CHEBI:37141

Chemical structure

Computed structure properties
Molecular formula	C11H13BrN2O5
Charge	0
Average mass	333.138 Da
Monoisotopic mass	332.00078 Da
Source	ChEBI
InChIKey	ODZBBRURCPAEIQ-PIXDULNESA-N

SMILES

O=c1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1/C=C/Br

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

Also called

Brivir (BRAND_NAME)— chebi
Mevir (BRAND_NAME)— chebi
Zostex (BRAND_NAME)— chebi
brivudina (INN)— chebi
brivudinum (INN)— chebi
5-[(E)-2-bromoethenyl]-2'-deoxyuridine (EXACT_SYNONYM)— chebi
(E)-5-(2-bromovinyl)-2'-deoxyuridine (EXACT_SYNONYM)— chebi
(E)-5-(2-bromovinyl)deoxyuridine (EXACT_SYNONYM)— chebi
5-[(1E)-2-bromoethenyl]-2'-deoxyuridine (EXACT_SYNONYM)— chebi
5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione (EXACT_SYNONYM)— chebi
5-bromovinyldeoxyuridine (EXACT_SYNONYM)— chebi
BVDU (EXACT_SYNONYM)— chebi
BVdU (EXACT_SYNONYM)— chebi
RP 101 (EXACT_SYNONYM)— chebi
RP-101 (EXACT_SYNONYM)— chebi
RP101 (EXACT_SYNONYM)— chebi
brivudin (EXACT_SYNONYM)— chebi
bromovinyldeoxyuridine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:69304-47-8
drugbank:DB03312
drugcentral:397
kegg.drug:D07249
patent:CN101066987
pdb-ccd:BVD
wikipedia.en:Brivudine

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:36044 CHEBI:36044

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:47278`	brivudine	`antibioticmech:chebi-7fab7a9368`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.