Cefroxadine
Identification
- Generic Name
- Cefroxadine
- DrugBank Accession Number
- DB11367
- Background
Cefroxadine is an orally available cephalosporin antibiotic. As part of its drug class, it shares structural properties to cefalexin as well as its activity spectrum. It was used in Italy but has since been withdrawn.
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
- Weight
- Average: 365.4
Monoisotopic: 365.104541898 - Chemical Formula
- C16H19N3O5S
- Synonyms
- Cefroxadine
- cefroxadino
- External IDs
- CGP 9000
- CGP-9000
Pharmacology
- Indication
Was used for the treatment of bacterial infections.
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- Pharmacodynamics
Cefroxadine is a cephalosporin antibiotic which produces a bactericidal effect on susceptible bacteria 1.
- Mechanism of action
Cefrixadine is a cephalosporin antibiotic, a class of β-lactam antibiotics similar to penicillins, which binds to and inhibits penicillin binding proteins (PBPs) 3. PBPs are responsible for catalyzing the transpeptidase reaction which cross-links the peptide side chains on the sugar residues of a peptidoglycan unit, adding the unit to the peptidoglycan layer. This disrupts the balance between the hydrolysis of peptidoglycan, in order to insert new peptidoglycan units, by murein hydrolase and the attachment of the new units which leads to overall destruction of the peptidoglycan layer. With the loss of its peptidoglycan layer the cell also loses its resistance to the high osmotic pressure inside its membrane and lyses.
Target Actions Organism APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) - Absorption
Oral bioavailability of 90% 2.
- Volume of distribution
Volume of distrubution of 15 L 2.
- Protein binding
Cefrixadine is 10% bound to human plasma proteins 2.
- Metabolism
- Not Available
- Route of elimination
Primarily eliminated in the urine (80-96%) 2.
- Half-life
The serum half life is 0.9-1.1 h 2.
- Clearance
The total body clearance is 340 mL/min and the renal clearance is 250 mL/min 2.
- Adverse Effects
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- Toxicity
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 Cefroxadine 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 Cefroxadine. Aceclofenac The risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Cefroxadine. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefroxadine is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefroxadine is combined with Acenocoumarol. - Food Interactions
- Not Available
Products
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- International/Other Brands
- Cefthan-DS (Novartis) / Oraspor (Novartis)
Categories
- ATC Codes
- J01DB11 — Cefroxadine
- 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 / Alpha amino acid amides / 1,3-thiazines / Vinylogous esters / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives / Monocarboxylic acids and derivatives show 8 more
- Substituents
- Aliphatic heteropolycyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Azacycle / Azetidine / Carbonyl group / Carboxamide group show 21 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:31379)
- Affected organisms
- Gram negative and gram positive bacteria
- Escherichia coli
- Salmonella typhi
- Staphylococcus aureus
- Proteus mirabilis
- Klebsiella pneumoniae
- Salmonella paratyphi
- Salmonella schottmuelleri
Chemical Identifiers
- UNII
- B908C4MV2R
- CAS number
- 51762-05-1
- InChI Key
- RDMOROXKXONCAL-UEKVPHQBSA-N
- InChI
- InChI=1S/C16H19N3O5S/c1-24-9-7-25-15-11(14(21)19(15)12(9)16(22)23)18-13(20)10(17)8-5-3-2-4-6-8/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(OC)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O
References
- Synthesis Reference
- R. Scartazzini, H. Bickel, DE 2331133; eidem, U.S. Patent 4,073,902 (1974, 1978 both to Ciba-Geigy).
- Jump up ^ R. B. Woodward and H. Bickel, U.S. Patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).
- General References
- Yasuda K, Kurashige S, Mitsuhashi S: Cefroxadine (CGP-9000), an orally active cephalosporin. Antimicrob Agents Chemother. 1980 Jul;18(1):105-10. [Article]
- Bergan T: Pharmacokinetic properties of the cephalosporins. Drugs. 1987;34 Suppl 2:89-104. [Article]
- 53. (2011). In Goodman and Gilman's the pharmacological basis of therapeutics, Pharmacological basis of therapeutics (12th ed.). New York: McGraw-Hill. [ISBN:9780071624428]
- External Links
- KEGG Drug
- D01528
- KEGG Compound
- C12979
- PubChem Compound
- 5284529
- PubChem Substance
- 347827975
- ChemSpider
- 4447587
- ChEBI
- 31379
- ChEMBL
- CHEMBL3186538
- ZINC
- ZINC000003830462
- Wikipedia
- Cefroxadine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.987 mg/mL ALOGPS logP 0.65 ALOGPS logP -3.4 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 3.28 Chemaxon pKa (Strongest Basic) 7.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 121.96 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 94.51 m3·mol-1 Chemaxon Polarizability 36.5 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014j-0239000000-baf73bdf127cc0ead515 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001c-0908000000-c816fdc98415da2863f9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05ir-0953000000-b563438765581da866b1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0abl-3925000000-40d95fa7499ee14b5f55 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-3942000000-c6b82a87aff370e3847b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9412000000-f89b226726f8d16c4032 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.3527089 predictedDarkChem Lite v0.1.0 [M-H]- 181.63167 predictedDeepCCS 1.0 (2019) [M+H]+ 188.1057089 predictedDarkChem Lite v0.1.0 [M+H]+ 183.98969 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.4040089 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.86205 predictedDeepCCS 1.0 (2019)
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 str...
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- Yasuda K, Kurashige S, Mitsuhashi S: Cefroxadine (CGP-9000), an orally active cephalosporin. Antimicrob Agents Chemother. 1980 Jul;18(1):105-10. [Article]
Enzymes
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Beta-lactamase activity
- Specific Function
- Not Available
- Gene Name
- blaZ
- Uniprot ID
- P00807
- Uniprot Name
- Beta-lactamase
- Molecular Weight
- 31348.98 Da
References
- Yasuda K, Kurashige S, Mitsuhashi S: Cefroxadine (CGP-9000), an orally active cephalosporin. Antimicrob Agents Chemother. 1980 Jul;18(1):105-10. [Article]
Drug created at February 10, 2016 22:35 / Updated at February 21, 2021 18:53