phosphonoformic acid
CHEBI:127780
·resolve ·ANTIVIRAL
·EXACT
REVIEWED
Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity. — ChEBI
Classification
Strictly broader compounds or drug classes this molecule belongs to.
Chemical structure
SMILES
O=C(O)P(=O)(O)O
InChI
InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)
Also called
- dihydroxyphosphanecarboxylic acid oxide (EXACT_SYNONYM)— chebi
- FOSCARNET (EXACT_SYNONYM)— chebi
- Foscarmet (EXACT_SYNONYM)— chebi
- Foscarnet (EXACT_SYNONYM)— chebi
- PHOSPHONOFORMIC ACID (EXACT_SYNONYM)— chebi
- carboxyphosphonic acid (EXACT_SYNONYM)— chebi
- foscarnet (EXACT_SYNONYM)— chebi
- phosphonomethanoic acid (EXACT_SYNONYM)— chebi
Cross-references
Identifiers for this same structure in other resources. An
accession that lands on two different structures in this corpus is withheld from
both rather than shown here, since it names at most one of them.
Drug registries
Identifiers that name a drug rather than a structure. One of
these can cover a parent compound, its salts and its stereoisomers, which this
corpus keeps as separate records, so it is not an equivalence of structure.
Patents and articles
Documents about this compound. A patent covers a class and an
article covers a topic; neither identifies a structure.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
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.
Molecular targets
The molecular entity or process this compound acts on. Each target
carries evidence — this is a mechanistic claim, not a classification.
viral family-B DNA polymerase active site VIRAL_PROTEIN DIRECT_BINDING_TARGET
Crystal structures used a bacteriophage RB69 polymerase engineered with variable elements from human cytomegalovirus UL54. The compound was resolved in the active site; this is a mechanistic model for UL54 inhibition, not a native-UL54 structure. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2011-05 (retrieved 2026-09-02).
- PMID:21566148 (Primary structural and biochemical mechanism study with an explicit chimeric-polymerase limitation.)
Mechanism summary
- Mode of action
- VIRAL_POLYMERASE_INHIBITION microbial target — CURATOR: PMID:21566148 visualized phosphonoformic acid in the active site of an engineered family-B DNA polymerase carrying human cytomegalovirus UL54 elements. It supports pyrophosphate mimicry and trapping of an untranslocated closed polymerase state, while the structure itself is a UL54-sensitive chimera rather than native UL54.
Record-level evidence
- PMID:21566148 (Primary polymerase active-site structure and inhibition-mechanism study.)
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
-
REVIEWED
2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, and antiviral class; curator-confirmed viral polymerase inhibition and added a directly observed active-site target with the chimeric-model limitation.
-
RESEEDED_FROM_SOURCES
2026-09-10 · 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 (YAML).
Explore across X-Mech:
MediaIngredientMech (phosphonoformic acid)
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· NaturalProductMech
· PathwayMech
· TraitMech