ertapenem

CHEBI:404903 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Meropenem in which the one of the two methyl groups attached to the amide nitrogen is replaced by hydrogen while the other is replaced by a 3-carboxyphenyl group. The sodium salt is used for the treatment of moderate to severe susceptible infections including intra-abdominal and acute gynaecological infections, pneumonia, and infections of the skin and of the urinary tract. — ChEBI

Classification

carbapenemARO:0000020

Strictly broader compounds or drug classes this molecule belongs to.

• carbapenemcarboxylic acid CHEBI:46634
• Label unavailable CHEBI:46770
• carbapenem ARO:0000020

Chemical structure

SMILES

[H][C@@]1(SC2=C(C(=O)O)N3C(=O)[C@]([H])([C@@H](C)O)[C@@]3([H])[C@H]2C)CN[C@]([H])(C(=O)Nc2cccc(C(=O)O)c2)C1

InChI

InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1

Also called

• (4R,5S,6S)-3-({(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
• (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid (EXACT_SYNONYM)— chebi
• (4R,5S,6S)-3-((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
• ERTAPENEM (EXACT_SYNONYM)— chebi
• ERT (EXACT_SYNONYM)— aro
• Invanz (EXACT_SYNONYM)— aro

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.

• ertapenemARO:0000070
• beilstein:9025520
• cas:153832-46-3
• chembl:CHEMBL1359
• pubchem.compound:150610

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.

• drugbank:DB00303
• drugcentral:1046
• kegg.drug:D07908

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

• patent:US5478820
• patent:WO9315078
• wikipedia.en:Ertapenem

Activity roles

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

• antimicrobial agent CHEBI:33281
• antibacterial agent CHEBI:33282
• antibacterial drug CHEBI:36047

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.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

4 observations · Browse all observations · Complete record (JSON.gz)

Resistance mechanisms

9 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank ertapenem-resistant Escherichia coli isolate MIC observation for AR-1305.

7. CURATED_RESISTANT_TAXA 2026-09-13 · codex · LLM-assisted

   Added two stable-URL CDC/FDA AR Isolate Bank Panel 10 ertapenem-resistant Klebsiella pneumoniae and Escherichia coli MIC observations for AR-0347 and AR-0348.

8. CURATED_RESISTANT_TAXA 2026-09-18 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank Panel 1168 ertapenem-resistant Klebsiella aerogenes MIC observation for AR-0074; preserved source Fluid Peritoneal, BioSample SAMN04014915, and Study ID CarbaNP-43 in evidence notes.

9. STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted

   Structured BioSample accessions on 4 activity_spectrum observation(s) where evidence notes already named exactly one accession.

Provenance

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

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