imipenem

CHEBI:471744 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A broad-spectrum, intravenous β-lactam antibiotic of the carbapenem subgroup. — 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.

carbapenems CHEBI:46633
β-lactam antibiotic allergen CHEBI:88225
carbapenem ARO:0000020

Chemical structure

Computed structure properties
Molecular formula	C12H17N3O4S
Charge	0
Average mass	299.352 Da
Monoisotopic mass	299.09398 Da
Source	ChEBI
InChIKey	ZSKVGTPCRGIANV-ZXFLCMHBSA-N

SMILES

[H]C(=N)NCCSC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@H](C)O)[C@@]2([H])C1

InChI

InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1

Also called

(5R,6S)-6-[(1R)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
(5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
(5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
(5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure (EXACT_SYNONYM)— chebi
Imipenem (EXACT_SYNONYM)— chebi
Imipenem anhydrous (EXACT_SYNONYM)— chebi
N-formimidoyl thienamycin (EXACT_SYNONYM)— chebi
N-formimidoylthienamycin (EXACT_SYNONYM)— chebi
imipenemum (EXACT_SYNONYM)— chebi
IMI (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.

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.

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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000170`	imipenem	`antibioticmech:aro-591797d15a`	2026-08-30
CHEBI	`CHEBI:471744`	imipenem	`antibioticmech:chebi-1f91c8b5f7`	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:3000170 (imipenem); 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.

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

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2024 M100 S34.	0297	BioSample SAMN04901687	Evidence Page data (JSON.gz)
Escherichia coli NCBITaxon:562	—	>16.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1305	BioSample SAMN46941623	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	8.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1149	BioSample SAMN34111336	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	4.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1150	BioSample SAMN34111337	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	8.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1151	BioSample SAMN34111338	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1152	BioSample SAMN34111339	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1153	BioSample SAMN34111340	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1155	BioSample SAMN34111341	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1156	BioSample SAMN34111342	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1157	BioSample SAMN34111343	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1158	BioSample SAMN34111344	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1159	BioSample SAMN34111345	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1161	BioSample SAMN34111347	Evidence Page data (JSON.gz)
Escherichia coli NCBITaxon:562	—	8.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1162	BioSample SAMN34111348	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1163	BioSample SAMN34111349	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1106	BioSample SAMN19970475	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1268	BioSample SAMN33435241	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	16.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1269	BioSample SAMN33435242	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	16.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1270	BioSample SAMN33435243	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1328	BioSample SAMN50502207	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; CDC/FDA AR Isolate Bank reports an R interpretation without a versioned breakpoint footnote on this isolate page.	0033	BioSample SAMN04014874	Evidence Page data (JSON.gz)
Klebsiella aerogenes NCBITaxon:548	—	4.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35 per the CDC/FDA AR Isolate Bank Panel 1168 footnote.	0074	BioSample SAMN04014915	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2024 M100 S34 per the CDC/FDA AR Isolate Bank Panel 1227 footnote.	0078	BioSample SAMN04014919	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	>64.0 mg/L	—	Broth microdilution imipenem MIC; modal MIC reported; interpreted using CLSI 2020 M100 S30 per the CDC/FDA AR Isolate Bank Panel 1227 footnote.	0083	BioSample SAMN04014924	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	CDC/FDA AR Isolate Bank imipenem MIC; interpreted using CLSI 2026 M100 Ed36 per the Panel 1394 footnote.	1332	—	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	>64.0 mg/L	—	CDC/FDA AR Isolate Bank imipenem MIC; interpreted using CLSI 2026 M100 Ed36 per the Panel 1394 footnote.	1333	—	Evidence Page data (JSON.gz)
Pseudomonas aeruginosa NCBITaxon:287	—	32.0 mg/L	—	CDC/FDA AR Isolate Bank imipenem MIC; interpreted using CLSI 2026 M100 S36 per the Panel 1394 footnote.	1334	—	Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_INACTIVATION 14

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
CAM-1	ARO:3004559	not organism-specific	—	ARO:3004559 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
FRI-11	ARO:3007632	not organism-specific	—	ARO:3007632 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
KPC-87	ARO:3007375	not organism-specific	—	ARO:3007375 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
NDM-1	ARO:3000589	not organism-specific	—	ARO:3000589 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
NDM-33	ARO:3007023	not organism-specific	—	ARO:3007023 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
OXA-1054	ARO:3009648	not organism-specific	—	ARO:3009648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
PJM-1	ARO:3007374	not organism-specific	—	ARO:3007374 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
VCC-1	ARO:3003713	not organism-specific	—	ARO:3003713 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
VIM-63	ARO:3005511	not organism-specific	—	ARO:3005511 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
VIM-92	ARO:3009643	not organism-specific	—	ARO:3009643 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
VMB-1	ARO:3005015	not organism-specific	—	ARO:3005015 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
WUS-1	ARO:3007435	not organism-specific	—	ARO:3007435 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
YEM-1	ARO:3007005	not organism-specific	—	ARO:3007005 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
crxA	ARO:3007118	not organism-specific	—	ARO:3007118 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 6

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii OprD conferring resistance to imipenem	ARO:3003809	not organism-specific	—	ARO:3003809 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
Burkholderia pseudomallei Omp38	ARO:3004123	not organism-specific	—	ARO:3004123 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
Klebsiella aerogenes Omp36	ARO:3003385	not organism-specific	—	ARO:3003385 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
Pseudomonas aeruginosa oprD with mutation conferring resistance to imipenem	ARO:3003686	not organism-specific	—	ARO:3003686 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
carO	ARO:3003808	not organism-specific	—	ARO:3003808 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 4

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
AdeIJK	ARO:3000772	not organism-specific	—	ARO:3000772 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnGH-TolC	ARO:3004598	not organism-specific	—	ARO:3004598 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
LptD	ARO:3005059	not organism-specific	—	ARO:3005059 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); database assertion, not a primary citation.)
MexPQ-OpmE	ARO:3003697	not organism-specific	—	ARO:3003697 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000170 (imipenem); 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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank imipenem-resistant Acinetobacter baumannii isolate MIC observation.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank imipenem-resistant Escherichia coli isolate MIC observation for AR-1305.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added 13 stable-URL CDC/FDA AR Isolate Bank imipenem-resistant Multi-Mechanism panel MIC observations for AR-1149, AR-1150, AR-1151, AR-1152, AR-1153, AR-1155, AR-1156, AR-1157, AR-1158, AR-1159, AR-1161, AR-1162, and AR-1163.
CURATED_RESISTANT_TAXA 2026-09-15 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 imipenem-resistant Pseudomonas aeruginosa MIC observation for AR-1106.
CURATED_RESISTANT_TAXA 2026-09-16 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 imipenem-resistant Pseudomonas aeruginosa MIC observation for AR-1268.
CURATED_RESISTANT_TAXA 2026-09-16 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 imipenem-resistant Pseudomonas aeruginosa MIC observation for AR-1269.
CURATED_RESISTANT_TAXA 2026-09-16 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 imipenem-resistant Pseudomonas aeruginosa MIC observation for AR-1270.
CURATED_RESISTANT_TAXA 2026-09-17 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 imipenem-resistant Pseudomonas aeruginosa MIC observation for AR-1328.
CURATED_RESISTANT_TAXA 2026-09-18 · codex · LLM-assisted
Added CDC/FDA AR Isolate Bank Panel 1227 isolate 0033 Acinetobacter baumannii imipenem MIC 64 mg/L with interpretation R; preserved source Unknown, BioSample SAMN04014874, Study ID CarbaNP-02, and MLST ST85(Pasteur)/ST1089(Oxford) in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-18 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1168 imipenem-resistant Klebsiella aerogenes MIC observation for AR-0074; preserved source Fluid Peritoneal, BioSample SAMN04014915, and Study ID CarbaNP-43 in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-19 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 imipenem-resistant Acinetobacter baumannii MIC observation for AR-0078; preserved source Pus, BioSample SAMN04014919, Study ID CarbaNP-47, and MLST ST229(Pasteur)/ST203(Oxford) in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-19 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 imipenem-resistant Acinetobacter baumannii MIC observation for AR-0083; preserved source Unknown, BioSample SAMN04014924, Study ID CarbaNP-52, and MLST ST1(Pasteur)/ST231/1604(Oxford) in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-20 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1394 imipenem-resistant Pseudomonas aeruginosa MIC observation for AR-1332; preserved source Urine, Study ID IMP-10, unavailable BioSample accession, and MLST ST357(Pasteur) in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-20 · codex · LLM-assisted
Added two stable-URL CDC/FDA AR Isolate Bank Panel 1394 imipenem-resistant Pseudomonas aeruginosa MIC observations for AR-1333 and AR-1334; preserved sources Urine and P-trap water, Study IDs IMP-11 and IMP-12, unavailable BioSample accessions, and MLST ST2731(Pasteur)/ST235(Pasteur) in evidence notes.
STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted
Structured BioSample accessions on 24 activity_spectrum observation(s) where evidence notes already named exactly one accession.
RESEEDED_FROM_SOURCES 2026-09-26 · seed_from_sources
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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