Pivampicillin (CED0010945)

Record Information

Version

1.0

Creation Date

2016-05-22 05:09:43 UTC

Update Date

2026-08-21 22:49:00 UTC

Accession Number

CHEM018331

Identification

Common Name

Pivampicillin

Class

Small Molecule

Description

Pivampicillin is an organic compound with the formula C22H29N3O6S and an average molecular weight of 463.55 g/mol. Pivampicillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target Penicillin-binding protein 1A (pbpA). The compound is identified in four recorded sources, including antibiotics and penicillins within healthcare, pharmaceuticals, and veterinary products. It is also found in household cleaning and consumer products, specifically non-electric simulated smoking devices, as well as in electrically stimulated smoking devices within electrical and electronic equipment. Recorded routes of exposure for pivampicillin include oral and inhalation.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ampicillin pivaloyloxymethyl ester	ChEBI
Pivaloyloxymethyl ampicillinate	ChEBI
Pivampicilina	ChEBI
Pivampicilline	ChEBI
Pivampicillinum	ChEBI
Pondocillin	Kegg
Pivaloyloxymethyl ampicillinic acid	Generator
Pivaloylampicillin	HMDB
Berocillin	HMDB
Serra pamies brand OF pivampicillin hydrochloride	HMDB
Pivampicillin hydrochloride	HMDB
Ampicillin pivaloyl ester	HMDB
Ester, ampicillin pivaloyl	HMDB
Hydrochloride, pivampicillin	HMDB
Leo brand OF pivampicillin	HMDB
Monohydrochloride, pivampicillin	HMDB
Pivamiser	HMDB
Pivampicillin monohydrochloride	HMDB

Chemical Formula

C₂₂H₂₉N₃O₆S

Average Molecular Mass

463.547 g/mol

Monoisotopic Mass

463.178 g/mol

CAS Registry Number

33817-20-8

IUPAC Name

[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

Traditional Name

pivampicillin

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C

InChI Identifier

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

InChI Key

ZEMIJUDPLILVNQ-ZXFNITATSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Triazoles

Direct Parent

Phenyl-1,2,4-triazoles

Alternative Parents

Substituents

Phenyl-1,2,4-triazole
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:49005 )
phenols (CHEBI:49005 )
benzoic acids (CHEBI:49005 )
triazoles (CHEBI:49005 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	1.43	ALOGPS
logP	2.07	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.03 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.25 m³·mol⁻¹	ChemAxon
Polarizability	47.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-4900000000-459356a4997f59da0598	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pi0-1922100000-c66d44e9e103153e78e7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4921000000-e513d7e709a4cc359313	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9800000000-1d45b7913c48a4570128	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0290100000-8fa5f97dea1c97508c9f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1691100000-3c1b28211f3589a2e3b9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ke9-9630000000-8cb9ef389fad4dc01d14	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ot-0322900000-3504b69e69554572682b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-7954200000-eb67af5b14cd5f26d30b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-5901000000-f16b60a416509c0adb29	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-1329700000-2f3c07f08b5464f78950	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-4934000000-ae133ff906d357093abb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9220000000-a556e0bfb78074f98c8d	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
6360.0	Log mg/kg	[3600:11000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
340	Penicillins	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
605	Pest Repellants	Agriculture & land management	Not Available

Pathways

1 pathway

Pivampicillin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	14.6357
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	7.39568
Click to view 3D structure	Baculoviral IAP repeat-containing protein 2	Q13490	Humans	Predicted (SEA)	35.0322
Click to view 3D structure	E3 ubiquitin-protein ligase XIAP	P98170	Humans	Predicted (SEA)	99.9584
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	0.700643
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	0.700643
Click to view 3D structure	Chymotrypsin-like elastase family member 2A	P08419	Sus scrofa	Predicted (SEA)	108.288
Click to view 3D structure	Cathepsin K	P43235	Humans	Predicted (SEA)	567.754
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	477.449
Click to view 3D structure	Neurogenic locus notch homolog protein 2	Q04721	Humans	Predicted (SEA)	10.5096
Click to view 3D structure	Neurogenic locus notch homolog protein 4	Q99466	Humans	Predicted (SEA)	10.5096
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	336.542
Click to view 3D structure	Procathepsin L	P07154	Rattus norvegicus	Predicted (SEA)	89.0595
Click to view 3D structure	Cathepsin S	P25774	Humans	Predicted (SEA)	746.885
Click to view 3D structure	Pancreatic alpha-amylase	P00689	Rattus norvegicus	Predicted (SEA)	20.2408
Click to view 3D structure	Pantothenate kinase, putative	Q8ILP4	Plasmodium falciparum (isolate 3D7)	Predicted (SEA)	76.2144
Click to view 3D structure	Cathepsin D	P07339	Humans	Predicted (SEA)	469.509
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	792.349
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	0.622794
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	659.227
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	850.658
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	2124.89
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	150.327
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	0.467095
Click to view 3D structure	Baculoviral IAP repeat-containing protein 8	Q96P09	Humans	Predicted (SEA)	16.3483