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 It was used in Italy but has since been withdrawn.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Withdrawn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
Thumb
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.

Pharmacology
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Drug Discovery
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Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
APenicillin-binding protein 1B
inhibitor
Escherichia 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.
DrugInteraction
AbacavirCefroxadine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefroxadine.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Cefroxadine.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Acemetacin is combined with Cefroxadine.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefroxadine is combined with Acenocoumarol.
AcetaminophenCefroxadine may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Cefroxadine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefroxadine.
AclidiniumCefroxadine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineCefroxadine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Interactions
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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
  1. Yasuda K, Kurashige S, Mitsuhashi S: Cefroxadine (CGP-9000), an orally active cephalosporin. Antimicrob Agents Chemother. 1980 Jul;18(1):105-10. [Article]
  2. Bergan T: Pharmacokinetic properties of the cephalosporins. Drugs. 1987;34 Suppl 2:89-104. [Article]
  3. 53. (2011). In Goodman and Gilman's the pharmacological basis of therapeutics, Pharmacological basis of therapeutics (12th ed.). New York: McGraw-Hill. [ISBN:9780071624428]
KEGG Drug
D01528
KEGG Compound
C12979
PubChem Compound
5284529
PubChem Substance
347827975
ChemSpider
4447587
ChEBI
31379
ChEMBL
CHEMBL3186538
ZINC
ZINC000003830462
Wikipedia
Cefroxadine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.987 mg/mLALOGPS
logP0.65ALOGPS
logP-3.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.96 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.51 m3·mol-1ChemAxon
Polarizability36.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
mrcB
Uniprot ID
P02919
Uniprot Name
Penicillin-binding protein 1B
Molecular Weight
94291.875 Da
References
  1. 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
  1. 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 on February 10, 2016 22:35 / Updated on February 21, 2021 18:53