Pivmecillinam (CED0008208)

Record Information

Version

1.0

Creation Date

2016-05-25 18:28:09 UTC

Update Date

2026-08-21 20:05:30 UTC

Accession Number

CHEM022320

Identification

Common Name

Pivmecillinam

Class

Small Molecule

Description

Pivmecillinam is an organic compound with the formula C21H33N3O5S and an average molecular weight of 439.57 g/mol. Pivmecillinam belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. The compound is recorded as being found in or released from three sources: pharmaceuticals and veterinary products, specifically antibiotics and penicillins, and household cleaning and consumer products, specifically non electric simulated smoking devices. Recorded exposure routes for this substance include oral and inhalation. Regarding its biological activity, pivmecillinam acts as an inhibitor of the protein target penicillin-binding protein 1A (pbpA).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Pivmecillinam	Kegg
PMPC	Kegg
Coactabs	Kegg
[(2S,5R,6R)-6-[(e)-[(Azepan-1-yl)methylidene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoic acid	Generator

Chemical Formula

C₂₁H₃₃N₃O₅S

Average Molecular Mass

439.570 g/mol

Monoisotopic Mass

439.214 g/mol

CAS Registry Number

32886-97-8

IUPAC Name

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

Traditional Name

pivmecillinam

SMILES

[H]\C(=N/[C@]1([H])C(=O)N2[C@]1([H])SC(C)(C)[C@]2([H])C(=O)OCOC(=O)C(C)(C)C)N1CCCCCC1

InChI Identifier

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/b22-12+/t14-,15+,17-/m1/s1

InChI Key

NPGNOVNWUSPMDP-UTEPHESZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Penam
Azepane
Acylal
Dicarboxylic acid or derivatives
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Carboxamide group
Carboxylic acid ester
Lactam
Acetal
Amidine
Formamidine
Carboxylic acid amidine
Azacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Hemithioaminal
Thioether
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.053 g/L	ALOGPS
logP	3.23	ALOGPS
logP	2.91	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	113.03 m³·mol⁻¹	ChemAxon
Polarizability	47.75 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 LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0lkc-0933100000-207d607d624521759c4a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066r-2911000000-e698803b355747dc85ad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9400000000-4c251e4b9870f1bb8e2e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0911000000-0118b6d73875ca106ecc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1931000000-ced5e83f734188289e15	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00c0-9612000000-5d2b3043f24082963710	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
8936.0	Log mg/kg	[5000:16000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
340	Penicillins	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Pivmecillinam Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Glyceraldehyde-3-phosphate dehydrogenase	P46406	Oryctolagus cuniculus	Predicted (SEA)	0.233548
Click to view 3D structure	Protein kinase C delta type	Q05655	Humans	Predicted (SEA)	3928.12
Click to view 3D structure	Beta-lactamase	P00811	Escherichia coli (strain K12)	Predicted (SEA)	30.1276
Click to view 3D structure	Protein kinase C alpha type	P17252	Humans	Predicted (SEA)	1949.19
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	3494.18
Click to view 3D structure	Beta-lactamase SHV-1	P0AD63	Escherichia coli	Predicted (SEA)	2.41333
Click to view 3D structure	Beta-lactamase TEM	P62593	Escherichia coli	Predicted (SEA)	8.71911
Click to view 3D structure	Protein kinase C epsilon type	Q02156	Humans	Predicted (SEA)	3104.63
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	7290.66
Click to view 3D structure	Lysosomal acid lipase/cholesteryl ester hydrolase	P38571	Humans	Predicted (SEA)	40.6373
Click to view 3D structure	Chymotrypsin-like elastase family member 2A	P08419	Sus scrofa	Predicted (SEA)	589.474
Click to view 3D structure	Beta-lactamase TEM	P62593	Escherichia coli	Predicted (SEA)	6.15009
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	4.67095
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	4796.6
Click to view 3D structure	Beta-lactamase	P00808	Bacillus licheniformis	Predicted (SEA)	1.40129
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	1.79053
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	1.79053
Click to view 3D structure	Immunoglobulin A1 protease autotransporter	P44969	Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)	Predicted (SEA)	85.5563
Click to view 3D structure	RAS guanyl-releasing protein 1	O95267	Humans	Predicted (SEA)	29.972
Click to view 3D structure	Beta-lactamase SHV-55	Q4TVR4	Klebsiella pneumoniae	Predicted (SEA)	2.49118
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	5859.09
Click to view 3D structure	Cholinesterase	P06276	Humans	Predicted (SEA)	4405.95
Click to view 3D structure	Penicillin-binding protein 2	Q53729	Staphylococcus aureus	Predicted (SEA)	1.32344
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	6803.24
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	6275.97