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

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

carbapenemARO:0000020

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:46634 CHEBI:46634
CHEBI:46770 CHEBI:46770
ARO:0000020 ARO:0000020

Chemical structure

Computed structure properties
Molecular formula	C22H25N3O7S
Charge	0
Average mass	475.523 Da
Monoisotopic mass	475.14132 Da
Source	ChEBI
InChIKey	JUZNIMUFDBIJCM-ANEDZVCMSA-N

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

Equivalent identifiers for this same structure in other resources.

ARO:0000070
beilstein:9025520
cas:153832-46-3
drugbank:DB00303
drugcentral:1046
kegg.drug:D07908
patent:US5478820
patent:WO9315078
wikipedia.en:Ertapenem
chembl:CHEMBL1359
pubchem.compound:150610

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:33282 CHEBI:33282
CHEBI:36047 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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:0000070`	ertapenem	`antibioticmech:aro-ac23aaf931`	2026-08-30
CHEBI	`CHEBI:404903`	ertapenem	`antibioticmech:chebi-f4e1cf82ea`	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.

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.)

Resistance mechanisms

9 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 7

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)
CTX-M-27	ARO:3001889	not organism-specific	—	ARO:3001889 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)
FRI-11	ARO:3007632	not organism-specific	—	ARO:3007632 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)
NDM-1	ARO:3000589	not organism-specific	—	ARO:3000589 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)
NDM-5	ARO:3000467	not organism-specific	—	ARO:3000467 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)
VCC-1	ARO:3003713	not organism-specific	—	ARO:3003713 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)
VIM-63	ARO:3005511	not organism-specific	—	ARO:3005511 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae KpnGH-TolC	ARO:3004598	not organism-specific	—	ARO:3004598 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000070 (ertapenem); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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 2026-08-31 · 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.