nirmatrelvir

CHEBI:170007 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

An azabicyclohexane that is (1R,5S)-3-azabicyclo[3.1.0]hexane substituted by {(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}aminoacyl, 3-methyl-N-(trifluoroacetyl)-L-valinamide, methyl and methyl groups at positions 2S, 3, 6 and 6, respectively. It is the first orally administered inhibitor of SARS-CoV-2 main protease developed by Pfizer and used in combination with ritonavir for the treatment of COVID-19. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:140326
Label unavailable CHEBI:170008
Label unavailable CHEBI:18379
Label unavailable CHEBI:37143
Label unavailable CHEBI:46770
Label unavailable CHEBI:74223

Chemical structure

Computed structure properties
Molecular formula	C23H32F3N5O4
Charge	0
Average mass	499.534 Da
Monoisotopic mass	499.24064 Da
Source	ChEBI
InChIKey	LIENCHBZNNMNKG-OJFNHCPVSA-N

SMILES

[H][C@@]1(C[C@@H](C#N)NC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)C(F)(F)F)C(C)(C)C)C[C@]3([H])C(C)(C)[C@]23[H])CCNC1=O

InChI

InChI=1S/C23H32F3N5O4/c1-21(2,3)16(30-20(35)23(24,25)26)19(34)31-10-13-14(22(13,4)5)15(31)18(33)29-12(9-27)8-11-6-7-28-17(11)32/h11-16H,6-8,10H2,1-5H3,(H,28,32)(H,29,33)(H,30,35)/t11-,12-,13-,14-,15-,16+/m0/s1

Also called

nirmatrelvirum (INN)— chebi
(1R,2S,5S)-N-{(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-N-(trifluoroacetyl)-L-valyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide (EXACT_SYNONYM)— chebi
PF 07321332 (EXACT_SYNONYM)— chebi
PF-07321332 (EXACT_SYNONYM)— chebi
PF07321332 (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.

cas:2628280-40-8

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.

wikipedia.en:Nirmatrelvir

Activity roles

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

anticoronaviral agent CHEBI:149553

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:170007`	nirmatrelvir	`antibioticmech:chebi-c288da7a4b`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

SARS-CoV-2 main protease (Mpro; 3CLpro) VIRAL_PROTEIN DIRECT_BINDING_TARGET

A compound-protease crystal structure directly established the complex. Enzyme kinetics subsequently measured nirmatrelvir potency against wild-type and six lineage-associated Mpro variants. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2021-10; 2022-02 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Replicase polyprotein 1ab `UniProtKB:P0DTD1` SARS-CoV-2 replicase polyprotein 1ab encoding the nsp5 3C-like main protease (Mpro/3CLpro) crystallized with PF-07321332 (nirmatrelvir) and assayed across lineage variants (PMID:34687004, PDB 7RF7; PMID:35182772).	rep	Severe acute respiratory syndrome coronavirus 2 `NCBITaxon:2697049`	REVIEWED

PMID:34687004 (Primary nirmatrelvir-Mpro crystal-structure report.)
PMID:35182772 (Primary enzyme-kinetics comparison of wild-type and six Mpro variants.)

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — CURATOR: PMID:34687004 reports the crystal structure of SARS-CoV-2 main protease in complex with PF-07321332 (nirmatrelvir), directly supporting the viral-protease target. PMID:35182772 measured similar in-vitro potency against wild-type enzyme and six catalytically competent variant proteases.

Record-level evidence

PMID:34687004 (Primary compound-target crystal-structure report.)
PMID:35182772 (Primary main-protease inhibition study across SARS-CoV-2 variants.)

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 SARS-CoV-2 main-protease inhibition and added the direct structural target with primary evidence.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated SARS-CoV-2 replicase polyprotein 1ab (P0DTD1) UniProtKB protein example on the PRIMARY_LITERATURE SARS-CoV-2 main protease (Mpro; 3CLpro) molecular target.

Provenance

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

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