ChemFOnt: Showing chemical card for Cefpimizole (CFc000022696)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:07 UTC

Chemfont ID

CFc000022696

Molecule Identification

Common Name

Cefpimizole

Definition

Cefpimizole is an antibiotic that belongs to the class of compounds known as cephalosporins (PMID: 3312705 ). Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to an oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. It is an anti-bacterial agent used in the treatment of uncomplicated genital or rectal infections (PMID: 3041630 ). Cefpimizole is also used to treat urethral infections caused by penicillinase-producing Neisseria gonorrhea (PPNG) (PMID: 6270834 ). It shows significant antibacterial activity against Pseudomonas aeruginosa, most members of the family Enterobacteriaceae, most Staphylococcus species, non-enterococcal Streptococcus species, Haemophilus influenzae, and Neisseria species (PMID: 4026275 ). It works by disrupting the synthesis of the peptidoglycan layer forming the bacterial cell wall. Cefpimizole is only found in individuals who have used or consumed this drug.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
U-63196cefpimizole	HMDB
AC 1370	HMDB
Cefpimizole sodium	HMDB
CPIZ	HMDB
7 beta-D-alpha-(4(5)-Carboxyimidazole-5(4)-carboxamido)phenylacetamido-3-(4-beta-sulfoethylpyridinium)methyl-3-cephem-4-carboxylic acid	HMDB
1-{[(6R,7R)-2-carboxy-7-{[(2R)-2-{[(5-carboxy-1H-imidazol-4-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-phenylethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-4-(2-sulphonatoethyl)pyridin-1-ium	HMDB
Cefpimizole	MeSH

Chemical Formula

C₂₈H₂₆N₆O₁₀S₂

Average Molecular Weight

670.67

Monoisotopic Molecular Weight

670.115182462

IUPAC Name

1-{[(6R,7R)-2-carboxy-7-{[(2R)-2-{[(5-carboxy-1H-imidazol-4-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-phenylethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-4-(2-sulfonatoethyl)pyridin-1-ium

Traditional Name

CAS Registry Number

84880-03-5

SMILES

[H][C@](N=C(O)C1=C(NC=N1)C(O)=O)(C(O)=N[C@]1([H])C(=O)N2C(C(O)=O)=C(C[N+]3=CC=C(CCS([O-])(=O)=O)C=C3)CS[C@]12[H])C1=CC=CC=C1

InChI Identifier

InChI=1S/C28H26N6O10S2/c35-23(18(16-4-2-1-3-5-16)31-24(36)19-20(27(38)39)30-14-29-19)32-21-25(37)34-22(28(40)41)17(13-45-26(21)34)12-33-9-6-15(7-10-33)8-11-46(42,43)44/h1-7,9-10,14,18,21,26H,8,11-13H2,(H5-,29,30,31,32,35,36,38,39,40,41,42,43,44)/t18-,21-,26-/m1/s1

InChI Key

LNZMRLHZGOBKAN-KAWPREARSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Phenylacetamide
Cephem
2-heteroaryl carboxamide
Imidazole-4-carbonyl group
Meta-thiazine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Pyridine
Pyridinium
Benzenoid
Alkanesulfonic acid
Vinylogous amide
Azole
Beta-lactam
Heteroaromatic compound
Imidazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Tertiary carboxylic acid amide
Lactam
Secondary carboxylic acid amide
Azetidine
Carboxamide group
Thioether
Dialkylthioether
Azacycle
Hemithioaminal
Organoheterocyclic compound
Carboxylic acid
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic zwitterion
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0041851)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	-0.39	ALOGPS
logP	-5.5	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	3.79	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	249.85 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	162.26 m³·mol⁻¹	ChemAxon
Polarizability	64.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041851

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

61863

KEGG Compound ID

C13024

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefpimizole

METLIN ID

Not Available

PubChem Compound

68597

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cefpimizole (CFc000022696)

MOL for CFc000022696 (Cefpimizole)

3D MOL for CFc000022696 (Cefpimizole)

3D SDF for CFc000022696 (Cefpimizole)

3D-SDF for CFc000022696 (Cefpimizole)

PDB for CFc000022696 (Cefpimizole)

3D PDB for CFc000022696 (Cefpimizole)

SMILES for CFc000022696 (Cefpimizole)

INCHI for CFc000022696 (Cefpimizole)

Structure for CFc000022696 (Cefpimizole)

3D Structure for CFc000022696 (Cefpimizole)