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Identification
NameCefonicid
Accession NumberDB01328
TypeSmall Molecule
GroupsApproved
DescriptionA second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections. [PubChem]
Structure
Thumb
Synonyms
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-8-oxo-3-({[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefonicid
Cefonicido
Cefonicidum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MonocidNot Available
PraticefNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefonicid sodium
ThumbNot applicableDBSALT001472
Categories
UNII6532B86WFG
CAS number61270-58-4
WeightAverage: 542.566
Monoisotopic: 542.034823652
Chemical FormulaC18H18N6O8S3
InChI KeyDYAIAHUQIPBDIP-AXAPSJFSSA-N
InChI
InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1
IUPAC Name
(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-8-oxo-3-({[1-(sulfomethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(CSC3=NN=NN3CS(O)(=O)=O)=C(N1C(=O)[[email protected]]2NC(=O)[[email protected]](O)C1=CC=CC=C1)C(O)=O
Pharmacology
IndicationFor the treatment of bacterial infections caused by susceptible microorganisms.
Structured Indications Not Available
PharmacodynamicsCefonicid is a second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections.
Mechanism of actionCefonicid, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
TargetKindPharmacological actionActionsOrganismUniProt ID
Penicillin-binding protein 1AProteinyes
inhibitor
Escherichia coli (strain K12)P02918 details
Peptidoglycan synthase FtsIProteinyes
inhibitor
Escherichia coli (strain K12)P0AD68 details
Penicillin-binding protein 1BProteinyes
inhibitor
Escherichia coli (strain K12)P02919 details
D-alanyl-D-alanine carboxypeptidase DacBProteinyes
inhibitor
Escherichia coli (strain K12)P24228 details
Penicillin-binding protein 2Proteinyes
inhibitor
Escherichia coli (strain K12)P0AD65 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding98% bound to plasma proteins.
Metabolism

Not metabolized.

Route of eliminationNot Available
Half life4.5 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolCefonicid may increase the anticoagulant activities of Acenocoumarol.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Cefonicid.Investigational
DicoumarolCefonicid may increase the anticoagulant activities of Dicoumarol.Approved
Ethyl biscoumacetateCefonicid may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCefonicid may increase the anticoagulant activities of Fluindione.Investigational
PhenindioneCefonicid may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonCefonicid may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefonicid.Approved
ProbenecidThe serum concentration of Cefonicid can be increased when it is combined with Probenecid.Approved
WarfarinCefonicid may increase the anticoagulant activities of Warfarin.Approved
Food InteractionsNot Available
References
Synthesis Reference

Theodore John Polansky, “Crystalline benzathine salt of cefonicid and its preparation.” U.S. Patent US5705496, issued October, 1992.

US5705496
General ReferencesNot Available
External Links
ATC CodesJ01DC06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9607
Blood Brain Barrier-0.9728
Caco-2 permeable-0.6466
P-glycoprotein substrateSubstrate0.6941
P-glycoprotein inhibitor INon-inhibitor0.7169
P-glycoprotein inhibitor IINon-inhibitor0.92
Renal organic cation transporterNon-inhibitor0.8219
CYP450 2C9 substrateNon-substrate0.84
CYP450 2D6 substrateNon-substrate0.8057
CYP450 3A4 substrateSubstrate0.5056
CYP450 1A2 substrateNon-inhibitor0.7321
CYP450 2C9 inhibitorNon-inhibitor0.7022
CYP450 2D6 inhibitorNon-inhibitor0.8516
CYP450 2C19 inhibitorNon-inhibitor0.68
CYP450 3A4 inhibitorNon-inhibitor0.7066
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6339
Ames testNon AMES toxic0.6105
CarcinogenicityCarcinogens 0.529
BiodegradationReady biodegradable0.9077
Rat acute toxicity2.5654 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9094
hERG inhibition (predictor II)Non-inhibitor0.7142
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.895 mg/mLALOGPS
logP-0.71ALOGPS
logP-2.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area204.91 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity136.58 m3·mol-1ChemAxon
Polarizability47.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • Benzenoid
  • Monocyclic benzene moiety
  • Meta-thiazine
  • Heteroaromatic compound
  • Alkanesulfonic acid
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular Weight:
93635.545 Da
References
  1. Rake JB, Newman DJ, Actor P: Affinity of cefonicid, a long-acting cephalosporin, for the penicillin-binding proteins of Escherichia coli K-12. J Antibiot (Tokyo). 1984 May;37(5):572-6. [PubMed:6376452 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular Weight:
63876.925 Da
References
  1. Rake JB, Newman DJ, Actor P: Affinity of cefonicid, a long-acting cephalosporin, for the penicillin-binding proteins of Escherichia coli K-12. J Antibiot (Tokyo). 1984 May;37(5):572-6. [PubMed:6376452 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular Weight:
94291.875 Da
References
  1. Rake JB, Newman DJ, Actor P: Affinity of cefonicid, a long-acting cephalosporin, for the penicillin-binding proteins of Escherichia coli K-12. J Antibiot (Tokyo). 1984 May;37(5):572-6. [PubMed:6376452 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name:
dacB
Uniprot ID:
P24228
Molecular Weight:
51797.85 Da
References
  1. Rake JB, Newman DJ, Actor P: Affinity of cefonicid, a long-acting cephalosporin, for the penicillin-binding proteins of Escherichia coli K-12. J Antibiot (Tokyo). 1984 May;37(5):572-6. [PubMed:6376452 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
Gene Name:
mrdA
Uniprot ID:
P0AD65
Molecular Weight:
70856.1 Da
References
  1. Rake JB, Newman DJ, Actor P: Affinity of cefonicid, a long-acting cephalosporin, for the penicillin-binding proteins of Escherichia coli K-12. J Antibiot (Tokyo). 1984 May;37(5):572-6. [PubMed:6376452 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other/unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Rodriguez CA, Smith DE: Influence of the unbound concentration of cefonicid on its renal elimination in isolated perfused rat kidneys. Antimicrob Agents Chemother. 1991 Nov;35(11):2395-400. [PubMed:1804013 ]
  2. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510 ]
  3. Benson JM, Boudinot FD, Pennell AT, Cunningham FE, DiPiro JT: In vitro protein binding of cefonicid and cefuroxime in adult and neonatal sera. Antimicrob Agents Chemother. 1993 Jun;37(6):1343-7. [PubMed:8328784 ]
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Drug created on June 30, 2007 11:48 / Updated on August 17, 2016 12:23