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.

CHEBI:46633 CHEBI:46633
CHEBI:88225 CHEBI:88225
ARO:0000020 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

Equivalent identifiers for this same structure in other resources.

ARO:3000170
beilstein:434624
cas:64221-86-9
drugbank:DB01598
drugcentral:1426
kegg.compound:C06665
kegg.drug:D04515
lincs.smallmolecule:LSM-6568
patent:BE848545
patent:US4194047
reaxys:434624
wikipedia.en:Imipenem
chembl:CHEMBL148
pubchem.compound:104838

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: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.)

Resistance mechanisms

24 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 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

Provenance

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