piperacillin

CHEBI:8232 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group. — 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

penicillin beta-lactamARO:3000008

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:17334 CHEBI:17334
CHEBI:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C23H27N5O7S
Charge	0
Average mass	517.564 Da
Monoisotopic mass	517.16312 Da
Source	ChEBI
InChIKey	IVBHGBMCVLDMKU-GXNBUGAJSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)c1ccccc1

InChI

InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1

Also called

6β-{(2R)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
Piperacillin (EXACT_SYNONYM)— chebi
Piperacillin anhydrous (EXACT_SYNONYM)— chebi
Piperacillin sodium (EXACT_SYNONYM)— aro
Pipercillin (EXACT_SYNONYM)— aro
Pipracil (EXACT_SYNONYM)— aro
Pipril (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000078
cas:61477-96-1
drugbank:DB00319
drugcentral:2187
kegg.compound:C14034
kegg.drug:D08380
lincs.smallmolecule:LSM-5924
patent:DE2519400
patent:US4087424
reaxys:6081140
wikipedia.en:Piperacillin
chembl:CHEMBL702
pubchem.compound:43672

Activity roles

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

CHEBI:33281 CHEBI:33281
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:0000078`	piperacillin	`antibioticmech:aro-923e37e9cc`	2026-08-30
CHEBI	`CHEBI:8232`	piperacillin	`antibioticmech:chebi-166ba03674`	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:0000078 (piperacillin); database assertion, not a primary citation.)

Resistance mechanisms

16 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 15

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ACC-1	ARO:3001815	not organism-specific	—	ARO:3001815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
Acinetobacter baumannii ampC beta-lactamase	ARO:3003796	not organism-specific	—	ARO:3003796 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
CAE-1	ARO:3007635	not organism-specific	—	ARO:3007635 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
EBR-5	ARO:3007437	not organism-specific	—	ARO:3007437 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
KBL-1	ARO:3007206	not organism-specific	—	ARO:3007206 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
MUS-1	ARO:3000843	not organism-specific	—	ARO:3000843 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
MUS-2	ARO:3003842	not organism-specific	—	ARO:3003842 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
OXA-1	ARO:3001396	not organism-specific	—	ARO:3001396 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
SED-1	ARO:3003561	not organism-specific	—	ARO:3003561 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
TUS-1	ARO:3000844	not organism-specific	—	ARO:3000844 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
VIM-92	ARO:3009643	not organism-specific	—	ARO:3009643 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); 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:0000078 (piperacillin); 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.