pivampicillin

CHEBI:8255 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin. — 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:136685 CHEBI:136685
CHEBI:51212 CHEBI:51212
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C22H29N3O6S
Charge	0
Average mass	463.556 Da
Monoisotopic mass	463.17771 Da
Source	ChEBI
InChIKey	ZEMIJUDPLILVNQ-ZXFNITATSA-N

SMILES

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

InChI

InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1

Also called

pivampicilina (INN)— chebi
pivampicilline (INN)— chebi
pivampicillinum (INN)— chebi
[(2,2-dimethylpropanoyl)oxy]methyl 6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylate (EXACT_SYNONYM)— chebi
ampicillin pivaloyloxymethyl ester (EXACT_SYNONYM)— chebi
pivaloyloxymethyl ampicillinate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009130
beilstein:5406076
cas:33817-20-8
drugbank:DB01604
drugcentral:2218
kegg.compound:C11750
kegg.drug:D08396
lincs.smallmolecule:LSM-6580
patent:CN101612154
patent:US3660575
wikipedia.en:Pivampicillin
chembl:CHEMBL3182343
pubchem.compound:33478

Activity roles

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

CHEBI:33281 CHEBI:33281

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:3009130`	pivampicillin	`antibioticmech:aro-504542943b`	2026-08-30
CHEBI	`CHEBI:8255`	pivampicillin	`antibioticmech:chebi-96b5c6f1b8`	2026-08-30

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

Provenance

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