adefovir

CHEBI:2469 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection. — 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:20706 CHEBI:20706
CHEBI:25698 CHEBI:25698
CHEBI:26069 CHEBI:26069

Chemical structure

Computed structure properties
Molecular formula	C8H12N5O4P
Charge	0
Average mass	273.189 Da
Monoisotopic mass	273.06269 Da
Source	ChEBI
InChIKey	SUPKOOSCJHTBAH-UHFFFAOYSA-N

SMILES

Nc1ncnc2c1ncn2CCOCP(=O)(O)O

InChI

InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)

Also called

{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid (EXACT_SYNONYM)— chebi
9-(2-(Phosphonomethoxy)ethyl)adenine (EXACT_SYNONYM)— chebi
9-(2-Phosphonylmethoxyethyl)adenine (EXACT_SYNONYM)— chebi
Adefovir (EXACT_SYNONYM)— chebi
DRG-0156 (EXACT_SYNONYM)— chebi
GS 0393 (EXACT_SYNONYM)— chebi
GS 393 (EXACT_SYNONYM)— chebi
GS-0393 (EXACT_SYNONYM)— chebi
HSDB 8079 (EXACT_SYNONYM)— chebi
N-(2-Phosphonylmethoxyethyl)adenine (EXACT_SYNONYM)— chebi
PMEA (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:106941-25-7
drugbank:DB00718
kegg.compound:C11277
kegg.drug:D02768
pdb-ccd:5HG
reaxys:3561094
wikipedia.en:Adefovir

Activity roles

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

CHEBI:36044 CHEBI:36044
CHEBI:53756 CHEBI:53756

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:2469`	adefovir	`antibioticmech:chebi-6c13d703a4`	2026-08-30

Mechanism summary

Mode of action: MULTIPLE microbial target — Assigned from ChEBI roles CHEBI:53756 (HIV-1 reverse transcriptase inhibitor), CHEBI:59517 (DNA synthesis inhibitor), which map to NUCLEIC_ACID_SYNTHESIS_INHIBITION, VIRAL_POLYMERASE_INHIBITION. ChEBI asserts these roles on the compound; a curator should decide whether one is primary. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. The contributing roles differ on whose target it is, so settling the primary mechanism may change mode_of_action_target_scope. Not a curator's mechanistic review.

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
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · 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.