Identification
- Generic Name
- Cefonicid
- DrugBank Accession Number
- DB01328
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cefonicid (DB01328)
- Weight
- Average: 542.566
Monoisotopic: 542.034823652 - Chemical Formula
- C18H18N6O8S3
- 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
Pharmacology
- Indication
For the treatment of bacterial infections caused by susceptible microorganisms.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Cefonicid 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 action
Cefonicid, 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.
Target Actions Organism APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacB inhibitorEscherichia coli (strain K12) APenicillin-binding protein 2 inhibitorEscherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
98% bound to plasma proteins.
- Metabolism
Not metabolized.
- Route of elimination
Not Available
- Half-life
4.5 hours
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cefonicid may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefonicid. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefonicid is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefonicid is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefonicid is combined with Acenocoumarol. Acetaminophen Cefonicid may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefonicid. Aclidinium Cefonicid may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cefonicid may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Cefonicid. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefonicid sodium F74MFL78A1 61270-78-8 NAXFZVGOZUWLEP-RFXDPDBWSA-L - International/Other Brands
- Monocid / Praticef
Categories
- ATC Codes
- J01DC06 — Cefonicid
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Phenylacetamides / Alkylarylthioethers / 1,3-thiazines / Tetrazoles / Tertiary carboxylic acid amides / Sulfonyls / Alkanesulfonic acids / Heteroaromatic compounds / Organosulfonic acids show 15 more
- Substituents
- Alcohol / Alkanesulfonic acid / Alkylarylthioether / Alpha-amino acid or derivatives / Aromatic alcohol / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole show 32 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:3491)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 6532B86WFG
- CAS number
- 61270-58-4
- InChI Key
- DYAIAHUQIPBDIP-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)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O
References
- Synthesis Reference
Theodore John Polansky, "Crystalline benzathine salt of cefonicid and its preparation." U.S. Patent US5705496, issued October, 1992.
US5705496- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015423
- KEGG Drug
- D07644
- KEGG Compound
- C06882
- PubChem Compound
- 43594
- PubChem Substance
- 46505699
- ChemSpider
- 39734
- 2183
- ChEBI
- 3491
- ChEMBL
- CHEMBL1601
- ZINC
- ZINC000003830428
- Therapeutic Targets Database
- DAP001173
- PharmGKB
- PA164743021
- Wikipedia
- Cefonicid
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Terminated Treatment Osteomyelitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular Injection, powder, for solution Intravenous Powder, for solution Injection, powder, for solution Powder Intramuscular Powder, for solution Intramuscular Powder, for solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.895 mg/mL ALOGPS logP -0.71 ALOGPS logP -2.5 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) -1.3 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 204.91 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 136.58 m3·mol-1 Chemaxon Polarizability 47.9 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9607 Blood Brain Barrier - 0.9728 Caco-2 permeable - 0.6466 P-glycoprotein substrate Substrate 0.6941 P-glycoprotein inhibitor I Non-inhibitor 0.7169 P-glycoprotein inhibitor II Non-inhibitor 0.92 Renal organic cation transporter Non-inhibitor 0.8219 CYP450 2C9 substrate Non-substrate 0.84 CYP450 2D6 substrate Non-substrate 0.8057 CYP450 3A4 substrate Substrate 0.5056 CYP450 1A2 substrate Non-inhibitor 0.7321 CYP450 2C9 inhibitor Non-inhibitor 0.7022 CYP450 2D6 inhibitor Non-inhibitor 0.8516 CYP450 2C19 inhibitor Non-inhibitor 0.68 CYP450 3A4 inhibitor Non-inhibitor 0.7066 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6339 Ames test Non AMES toxic 0.6105 Carcinogenicity Carcinogens 0.529 Biodegradation Ready biodegradable 0.9077 Rat acute toxicity 2.5654 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9094 hERG inhibition (predictor II) Non-inhibitor 0.7142
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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 str...
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- 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. [Article]
- 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 fr...
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- 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. [Article]
- 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 str...
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- 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. [Article]
- 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
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacB
- Molecular Weight
- 51797.85 Da
References
- 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. [Article]
- 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
- Uniprot Name
- Penicillin-binding protein 2
- Molecular Weight
- 70856.1 Da
References
- 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. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- 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 colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- 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. [Article]
- Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [Article]
- 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. [Article]
Drug created at June 30, 2007 17:48 / Updated at June 12, 2020 16:51