tenofovir disoproxil

CHEBI:63717 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An organic phosphonate that is the disoproxil ester of tenofovir. A prodrug for tenofovir, an HIV-1 reverse transcriptase inhibitor, tenofovir disoproxil is used as the fumaric acid salt in combination therapy for the treatment of HIV 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:37592 CHEBI:37592

Chemical structure

Computed structure properties
Molecular formula	C19H30N5O10P
Charge	0
Average mass	519.448 Da
Monoisotopic mass	519.17303 Da
Source	ChEBI
InChIKey	JFVZFKDSXNQEJW-CQSZACIVSA-N

SMILES

CC(C)OC(=O)OCOP(=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)OCOC(=O)OC(C)C

InChI

InChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1

Also called

bis({[(propan-2-yloxy)carbonyl]oxy}methyl) ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate (EXACT_SYNONYM)— chebi
9-((R)-2-((bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine (EXACT_SYNONYM)— chebi
PMPA prodrug (EXACT_SYNONYM)— chebi
bis(POC)PMPA (EXACT_SYNONYM)— chebi
tenofovir bis(isopropyloxycarbonyloxymethyl) ester (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:201341-05-1
drugbank:DB00300
drugcentral:2593
patent:WO5922695
patent:WO9804569
reaxys:9018187

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:63717`	tenofovir disoproxil	`antibioticmech:chebi-447f69ed2b`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see 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

Provenance

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