carbenicillin

CHEBI:3393 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin antibiotic having a 6β-2-carboxy-2-phenylacetamido side-chain. — 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	C17H18N2O6S
Charge	0
Average mass	378.406 Da
Monoisotopic mass	378.08856 Da
Source	ChEBI
InChIKey	FPPNZSSZRUTDAP-UWFZAAFLSA-N

SMILES

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

InChI

InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1

Also called

carbenicilina (INN)— chebi
carbenicilline (INN)— chebi
carbenicillinum (INN)— chebi
6β-(2-carboxy-2-phenylacetamido)-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
CBPC (EXACT_SYNONYM)— chebi
N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid (EXACT_SYNONYM)— chebi
carboxybenzylpenicillin (EXACT_SYNONYM)— chebi
α-carboxybenzylpencillin (EXACT_SYNONYM)— chebi
α-phenyl(carboxymethylpenicillin) (EXACT_SYNONYM)— chebi
Anabactyl (EXACT_SYNONYM)— aro
CAR (EXACT_SYNONYM)— aro
Carbecin (EXACT_SYNONYM)— aro
Carbenicilina (EXACT_SYNONYM)— aro
Carbenicillina (EXACT_SYNONYM)— aro
Carbenicilline (EXACT_SYNONYM)— aro
Carbenicillinum (EXACT_SYNONYM)— aro
Geopen (EXACT_SYNONYM)— aro
Microcillin (EXACT_SYNONYM)— aro
Pyopen (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000043
cas:4697-36-3
drugbank:DB00578
drugcentral:492
hmdb:HMDB0014717
kegg.compound:C06869
kegg.drug:D07614
patent:US3142673
reaxys:1230663
wikipedia.en:Carbenicillin
chembl:CHEMBL1214
pubchem.compound:20824

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:0000043`	carbenicillin	`antibioticmech:aro-dbf9d624bc`	2026-08-30
CHEBI	`CHEBI:3393`	carbenicillin	`antibioticmech:chebi-14f03d0274`	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:0000043 (carbenicillin); database assertion, not a primary citation.)

Resistance mechanisms

4 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 2

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
WUS-1	ARO:3007435	not organism-specific	—	ARO:3007435 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000043 (carbenicillin); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000043 (carbenicillin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii AbuO	ARO:3004578	not organism-specific	—	ARO:3004578 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000043 (carbenicillin); database assertion, not a primary citation.)

UNKNOWN 1

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
PvrR	ARO:3003688	not organism-specific	—	ARO:3003688 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000043 (carbenicillin); 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.