bacampicillin

CHEBI:2968 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:51212 CHEBI:51212

Chemical structure

Computed structure properties
Molecular formula	C21H27N3O7S
Charge	0
Average mass	465.528 Da
Monoisotopic mass	465.15697 Da
Source	ChEBI
InChIKey	PFOLLRNADZZWEX-FFGRCDKISA-N

SMILES

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

InChI

InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1

Also called

bacampicilina (INN)— chebi
bacampicilline (INN)— chebi
1-[(ethoxycarbonyl)oxy]ethyl 6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylate (EXACT_SYNONYM)— chebi
1'-ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanate (EXACT_SYNONYM)— chebi
1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (EXACT_SYNONYM)— chebi
bacampicillinum (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:50972-17-3
drugbank:DB01602
drugcentral:280
hmdb:HMDB0015540
kegg.compound:C08122
kegg.drug:D07487
patent:DE2144457
patent:US3873521
patent:US3939270
reaxys:5784318
wikipedia.en:Bacampicillin

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
CHEBI	`CHEBI:2968`	bacampicillin	`antibioticmech:chebi-b8a1ee62ed`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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.