Cefprozil (CED0008668)

Record Information

Version

1.0

Creation Date

2016-05-25 18:25:32 UTC

Update Date

2026-08-20 00:09:58 UTC

Accession Number

CHEM022248

Identification

Common Name

Cefprozil

Class

Small Molecule

Description

Cefprozil is an organic compound with the chemical formula C18H19N3O5S and an average molecular weight of 389.43 g/mol. Cefprozil belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. The compound is found in or released from four recorded sources. These include pharmaceuticals and veterinary products, specifically antibiotics and beta-lactam antibacterials, as well as household cleaning and consumer products, including other smoking requisites and non electric simulated smoking devices. Recorded exposure routes for this substance include oral and inhalation. In terms of biological activity, cefprozil acts on three recorded protein targets. It functions as an inhibitor of Penicillin-binding protein 1A (ponA), Penicillin-binding protein 2B (penA), and Penicillin-binding protein 2x (pbpX).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cefprozil anhydrous	Kegg
Cefzil	Kegg
(6R,7R)-7-{[(2R)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-7-[[(2R)-2-amino-2-(4-Hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
Arzimol	MeSH
Brisoral	MeSH
Cefprozil	MeSH
7-(2-amino-2-(4-Hydroxyphenyl)acetamido)-3-(propenyl)-3-cephem-4-carboxylic acid monohydrate	MeSH
Procef	MeSH
Cefprozil monohydrate	MeSH
7-(2-Amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid	MeSH

Chemical Formula

C₁₈H₁₉N₃O₅S

Average Molecular Mass

389.430 g/mol

Monoisotopic Mass

389.105 g/mol

CAS Registry Number

92665-29-7

IUPAC Name

(6R,7R)-7-{[(2R)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

cefzil

SMILES

[H]\C(C)=C(\[H])C1=C(N2C(=O)[C@@]([H])(N=C(O)[C@]([H])(N)C3=CC=C(O)C=C3)[C@@]2([H])SC1)C(O)=O

InChI Identifier

InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1

InChI Key

WDLWHQDACQUCJR-ZAMMOSSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Indole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
1,2-aminoalcohol
Secondary amine
Azacycle
Secondary aliphatic amine
Ether
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:3441 )
secondary amino compound (CHEBI:3441 )
carbazoles (CHEBI:3441 )

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	0.11 g/L	ALOGPS
logP	0.42	ALOGPS
logP	-1.3	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.79 m³·mol⁻¹	ChemAxon
Polarizability	38.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05gl-1943000000-6526026e86cd6cb96fd1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05gr-2920000000-447f3c6096761601c2ad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fu-9800000000-275068d6b12d7913192e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0293000000-a70c986a5eaba361d943	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pbc-2962000000-96705de3fccd000e4cef	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-9510000000-f2fbc8ecdc72ddbe848a	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
8238.0	Log mg/kg	[4600:15000]	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
341	Beta-lactam antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Cefprozil Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	2.41333
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	2.88042
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	194.0
Click to view 3D structure	Solute carrier family 22 member 11	Q9NSA0	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	385.587
Click to view 3D structure	Solute carrier family 15 member 2	Q16348	Humans	Predicted (SEA)	98.4014
Click to view 3D structure	Solute carrier family 15 member 2	Q63424	Rattus norvegicus	Predicted (SEA)	48.033
Click to view 3D structure	Apoptotic protease-activating factor 1	O14727	Humans	Predicted (SEA)	892.152
Click to view 3D structure	Beta-lactamase	B2ZTR6	Acinetobacter baumannii	Predicted (SEA)	1.24559
Click to view 3D structure	ADC-11	D6NSM8	Acinetobacter baumannii	Predicted (SEA)	1.24559
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	Q06124	Humans	Predicted (SEA)	1325.31
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2B	Q13224	Humans	Predicted (SEA)	1064.35
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	2645.63
Click to view 3D structure	Sigma intracellular receptor 2	Q5U3Y7	Rattus norvegicus	Predicted (SEA)	1821.36
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	5797.51
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	5969.87
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	4917.35
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	5758.82
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	5764.89
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	4929.26
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	5075.22
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	2264.87
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	3754.36
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	4521.56