AntibioticMech

pivmecillinam

CHEBI:51210 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillanic acid ester that is the [(2,2-dimethylpropanoyl)oxy]methyl ester and prodrug of mecillinam. — ChEBI

Classification

penicillin beta-lactamARO:3000008

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:136685 CHEBI:136685
• CHEBI:17334 CHEBI:17334
• CHEBI:51212 CHEBI:51212
• ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties

Molecular formula	C21H33N3O5S
Charge	0
Average mass	439.578 Da
Monoisotopic mass	439.21409 Da
Source	ChEBI
InChIKey	NPGNOVNWUSPMDP-HLLBOEOZSA-N

SMILES

[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1

InChI

InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1

Also called

• pivmecilinamo (INN)— chebi
• pivmecillinamum (INN)— chebi
• [(2,2-dimethylpropanoyl)oxy]methyl 6β-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3α-carboxylate (EXACT_SYNONYM)— chebi
• [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (EXACT_SYNONYM)— chebi
• amdinocillin pivoxil (EXACT_SYNONYM)— chebi
• amdinocillin, pivaloyloxymethyl ester (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3007529
• beilstein:9014155
• cas:32886-97-8
• drugbank:DB01605
• lincs.smallmolecule:LSM-3494
• patent:DE2055531
• patent:US3957764
• chembl:CHEMBL1650818
• pubchem.compound:115163

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:3007529	pivmecillinam	antibioticmech:aro-a8936e1053	2026-08-30
CHEBI	CHEBI:51210	pivmecillinam	antibioticmech:chebi-2fa06d03f8	2026-08-30

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. 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.