Pivampicillin

Summary

Pivampicillin (CHEMBL3182343) is an approved small-molecule prodrug (ATC J01CA02); indicated across 1 condition including bacterial infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01CA02
• Indications: 1 condition
• Chemistry: 463.5 Da · C22H29N3O6S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL3182343
Name	Pivampicillin
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	33478
ChEBI	CHEBI:8255
ATC	J01CA02
Molecular formula	C22H29N3O6S
Molecular weight	463.5
InChIKey	ZEMIJUDPLILVNQ-ZXFNITATSA-N

SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)C(C)(C)C)C

IUPAC name: 2,2-dimethylpropanoyloxymethyl (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

ChEBI definition: A penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin.

Pharmacological roles (ChEBI): prodrug.

Also known as: MK-191, Pivampicilina, Pivampicillin, Pivampicilline, Pondocillin, SID11112735, PIVAMPICILLINE, SID170466065, SID144204182, PIVAMPICILLIN, pivampicillin, PIVAMPICILLIN 6BETA-BROMOPENICILLANATE

Parent form; salt/anhydrous children: CHEMBL3989412, CHEMBL3989898

Patent coverage: 1,452 distinct patent families (5,357 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Ubiquitin carboxyl-terminal hydrolase 2, Muscarinic acetylcholine receptor M1, Prostaglandin G/H synthase 1, Cytochrome P450 3A4.

Bioactivity

ChEMBL activities: 5 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
USP2	5.6	Potency	2512	nM	CHEMBL_ACT_4691720
CYP3A4	5.3	Potency	5012	nM	CHEMBL_ACT_5005947
CYP3A4	5.3	Potency	5012	nM	CHEMBL_ACT_5074411
CYP3A4	5.3	AC50	5012	nM	CHEMBL_ACT_6053276
PTGS1	5.13	AC50	7483	nM	CHEMBL_ACT_25205149

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 indication (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).