Identification

Name
Cefuroxime
Accession Number
DB01112  (APRD00285)
Type
Small Molecule
Groups
Approved
Description

Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus. [PubChem]

Structure
Thumb
Synonyms
  • (6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefuroxim
  • Cefuroxime
  • Cefuroximo
  • Cefuroximum
  • Cephuroxime
  • Zinacef danmark
Product Ingredients
IngredientUNIICASInChI Key
Cefuroxime axetilZ49QDT0J8Z64544-07-6KEJCWVGMRLCZQQ-YJBYXUATSA-N
Cefuroxime sodiumR8A7M9MY6156238-63-2URDOHUPGIOGTKV-JTBFTWTJSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-cefuroximeTablet250 mgOralAurobindo Pharma Limited (Unit Vi)2012-01-13Not applicableCanada
Auro-cefuroximeTablet500 mgOralAurobindo Pharma Limited (Unit Vi)2012-01-13Not applicableCanada
CeftinPowder, for suspension250 mg/5mLOralGlaxosmithkline Inc2004-06-022018-09-30Us
CeftinPowder, for suspension250 mg/5mLOralA S Medication Solutions2004-06-022017-06-20Us
CeftinTablet, film coated250 mg/1OralGlaxosmithkline Inc1989-10-012018-04-30Us00173 0387 00 nlmimage10 8018c066
CeftinTablet, film coated500 mg/1OralGlaxosmithkline Inc1989-10-012017-04-30Us00173 0394 00 nlmimage10 7d18beb5
CeftinPowder, for suspension125 mg/5mLOralGlaxosmithkline Inc2004-06-022018-09-30Us
Ceftin - Pwr 250mg/sachetPowder250 mgOralGlaxosmithkline Inc1999-11-102003-02-07Canada
Ceftin - Pws 125mg/5mlPowder, for solution125 mgOralGlaxosmithkline Inc1999-09-13Not applicableCanada
Ceftin - Tab 250mgTablet250 mgOralGlaxosmithkline Inc1998-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cefuroximeTablet250 mgOralApotex Corporation2001-08-29Not applicableCanada
Apo-cefuroximeTablet500 mgOralApotex Corporation2001-08-29Not applicableCanada
CefuroximeInjection, powder, for solution90 mg/mLIntravenousHospira, Inc.2009-04-272016-10-13Us
CefuroximeInjection, powder, for solution1.5 g/16mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution7.5 g/80mLIntravenousAPP Pharmaceuticals, Inc.2010-07-30Not applicableUs
CefuroximeInjection, powder, for solution750 mg/1Intramuscular; IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution1.5 g/1IntravenousWest Ward Pharmaceutical2004-01-09Not applicableUs
CefuroximeInjection, powder, for solution1.5 g/100mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUs
CefuroximeInjection, powder, for solution750 mg/1Intramuscular; IntravenousAPP Pharmaceuticals, Inc.2011-05-24Not applicableUs
CefuroximeInjection, powder, for solution7.5 g/82.5mLIntravenousSagent Pharmaceuticals2008-05-012016-10-13Us
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefuroxime AxetilTablet500 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2003-07-25Not applicableUs
International/Other Brands
Cefurax (Lindopharm) / Elobact (GlaxoSmithKline) / Oraxim (Malesci) / Sharox (Fahrenheit) / Supacef (GlaxoSmithKline) / Zinnat (GlaxoSmithKline)
Categories
UNII
O1R9FJ93ED
CAS number
55268-75-2
Weight
Average: 424.385
Monoisotopic: 424.068884198
Chemical Formula
C16H16N4O8S
InChI Key
JFPVXVDWJQMJEE-IZRZKJBUSA-N
InChI
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
IUPAC Name
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][[email protected]]12SCC(COC(N)=O)=C(N1C(=O)[[email protected]]2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O

Pharmacology

Indication

For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.

Structured Indications
Pharmacodynamics

Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug

Mechanism of action

Cefuroxime, 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; it is possible that cefuroxime interferes with an autolysin inhibitor.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Clostridium perfringens (strain 13 / Type A)
Absorption

Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).

Volume of distribution
Not Available
Protein binding

50% to serum protein

Metabolism

The axetil moiety is metabolized to acetaldehyde and acetic acid.

Route of elimination
Not Available
Half life

Approximately 80 minutes following intramuscular or intravenous injection.

Clearance
Not Available
Toxicity

Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolCefuroxime may increase the anticoagulant activities of Acenocoumarol.Approved
AlgeldrateThe serum concentration of Cefuroxime can be decreased when it is combined with Algeldrate.Approved, Experimental
AlmagateThe serum concentration of Cefuroxime can be decreased when it is combined with Almagate.Experimental
AlmasilateThe serum concentration of Cefuroxime can be decreased when it is combined with Almasilate.Approved, Experimental
AloglutamolThe serum concentration of Cefuroxime can be decreased when it is combined with Aloglutamol.Experimental
AluminiumThe serum concentration of Cefuroxime can be decreased when it is combined with Aluminium.Approved
Aluminium acetoacetateThe serum concentration of Cefuroxime can be decreased when it is combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe serum concentration of Cefuroxime can be decreased when it is combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Aluminum hydroxide.Approved
AsenapineAsenapine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Cefuroxime.Investigational
Bismuth SubcitrateThe serum concentration of Cefuroxime can be decreased when it is combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe serum concentration of Cefuroxime can be decreased when it is combined with Bismuth subnitrate.Experimental
Calcium CarbonateThe serum concentration of Cefuroxime can be decreased when it is combined with Calcium Carbonate.Approved
Calcium silicateThe serum concentration of Cefuroxime can be decreased when it is combined with Calcium silicate.Experimental
CimetidineCimetidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ClorindioneCefuroxime may increase the anticoagulant activities of Clorindione.Experimental
DicoumarolCefuroxime may increase the anticoagulant activities of Dicoumarol.Approved
DiphenadioneCefuroxime may increase the anticoagulant activities of Diphenadione.Experimental
DoxepinDoxepin can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
EpinastineEpinastine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Ethyl biscoumacetateCefuroxime may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FamotidineFamotidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
FluindioneCefuroxime may increase the anticoagulant activities of Fluindione.Investigational
HydrotalciteThe serum concentration of Cefuroxime can be decreased when it is combined with Hydrotalcite.Experimental, Investigational
MagaldrateThe serum concentration of Cefuroxime can be decreased when it is combined with Magaldrate.Approved, Withdrawn
Magnesium HydroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium oxide.Approved
Magnesium peroxideThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium peroxide.Experimental
Magnesium silicateThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium silicate.Approved, Experimental
Magnesium TrisilicateThe serum concentration of Cefuroxime can be decreased when it is combined with Magnesium Trisilicate.Approved
MethanthelineMethantheline can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
MetiamideMetiamide can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
NizatidineNizatidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
OlanzapineOlanzapine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
PhenindioneCefuroxime may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonCefuroxime may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefuroxime.Approved
ProbenecidThe serum concentration of Cefuroxime can be increased when it is combined with Probenecid.Approved
PromethazinePromethazine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
RanitidineRanitidine can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Roxatidine acetateRoxatidine acetate can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Sodium bicarbonateThe serum concentration of Cefuroxime can be decreased when it is combined with Sodium bicarbonate.Approved
TioclomarolCefuroxime may increase the anticoagulant activities of Tioclomarol.Experimental
TromethamineThe serum concentration of Cefuroxime can be decreased when it is combined with Tromethamine.Approved
WarfarinCefuroxime may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
  • Take with food to increase absorption.

References

Synthesis Reference

Vijay Kumar Handa, Ramesh Dandala, Jag Mohan Khanna, "Process for the preparation of cefuroxime." U.S. Patent US6235896, issued February, 1976.

US6235896
General References
  1. Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. [PubMed:8799689]
External Links
Human Metabolome Database
HMDB15244
KEGG Drug
D00262
KEGG Compound
C06894
PubChem Compound
5479529
PubChem Substance
46506681
ChemSpider
4586393
BindingDB
50422689
ChEBI
3515
ChEMBL
CHEMBL1436
Therapeutic Targets Database
DAP000445
PharmGKB
PA448868
HET
KOV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cefuroxime
ATC Codes
S01AA27 — CefuroximeJ01DC02 — CefuroximeJ01RA03 — Cefuroxime and metronidazole
AHFS Codes
  • 08:12.06.08 — Second Generation Cephalosporins
PDB Entries
4kov
FDA label
Download (809 KB)
MSDS
Download (52.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionComplications of Surgical Procedures1
0RecruitingTreatmentOsteomyelitis1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
3CompletedPreventionAcute Appendicitis / Perforated Gastroduodenal Ulcer / Small intestinal obstruction1
3CompletedTreatmentPneumonia1
3RecruitingTreatmentEnterobacteriaceae Infections1
4Active Not RecruitingTreatmentInfection NOS1
4CompletedPreventionInfection NOS1
4CompletedPreventionInfection Prophylaxis in Colo Rectal Surgery1
4CompletedPreventionInfection, Postoperative Wound1
4CompletedPreventionPostoperative Infections1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentComplications; Cesarean Section / Infection, Postoperative Wound / Infection; Cesarean Section1
4CompletedTreatmentErythema Chronicum Migrans / Post-Lyme Disease Symptoms1
4CompletedTreatmentKnee Osteoarthritis (Knee OA)1
4CompletedTreatmentWound Infections1
4RecruitingPreventionInfection, Postoperative Wound1
4RecruitingPreventionObesity; Drug1
4WithdrawnTreatmentPostoperative Infections1
Not AvailableCompletedPreventionEndophthalmitis1
Not AvailableCompletedSupportive CareOsteoarthritis (OA) / Post-traumatic; Arthrosis1
Not AvailableCompletedTreatmentCataracts / Endophthalmitis1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableNot Yet RecruitingNot AvailableCardiovascular Events1
Not AvailableUnknown StatusPreventionCystocele / Enterocele / Rectocele / Uterine Prolapse1
Not AvailableUnknown StatusPreventionInfection NOS1
Not AvailableUnknown StatusPreventionPeristomal Wound Infection After the Operation of PEG / Prophylactic Antibiotics Before PEG / The Patients Who Receive Percutaneous Endoscopic Gastrostomy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
PowderOral250 mg
Powder, for solutionOral125 mg
TabletOral250 mg
TabletOral500 mg
Powder, for solutionOral250 mg
Injection, powder, for solutionIntramuscular; Intravenous750 mg/1
Injection, powder, for solutionIntravenous1.5 g/1
Injection, powder, for solutionIntravenous1.5 g/16mL
Injection, powder, for solutionIntravenous1.5 g/100mL
Injection, powder, for solutionIntravenous7.5 g/82.5mL
Injection, powder, for solutionIntravenous7.5 g/1
Injection, powder, for solutionIntravenous7.5 g/80mL
Injection, powder, for solutionIntravenous750 mg/8mL
Injection, powder, for solutionIntravenous750 mg/100mL
Injection, powder, for solutionIntravenous90 mg/mL
TabletOral125 mg/1
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral125 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
SuspensionOral125 mg/5mL
SuspensionOral250 mg/mL
Powder, for solutionIntravenous7.5 g
Powder, for solutionIntravenous750 mg
Injection, powder, for solutionIntravenous225 g/1
Injection, powder, for solutionIntravenous75 g/1
Powder, for solutionIntravenous1.5 g
TabletOral125 mg
Injection, powder, for solutionIntramuscular; Intravenous90 mg/mL
Injection, solutionIntravenous1.5 g/50mL
Powder, for solutionIntramuscular; Intravenous1.5 g
Powder, for solutionIntramuscular; Intravenous750 mg
Prices
Unit descriptionCostUnit
Rocephin 10 gm vial478.32USD vial
Ceftin 20 500 mg tablet Bottle436.36USD bottle
Cefuroxime Axetil 250 mg/5ml Suspension 100ml Bottle121.27USD bottle
Rocephin 2 gm vial97.5USD vial
Cefzil 250 mg/5ml Suspension 100ml Bottle87.62USD bottle
Zinacef 7.5 gm vial65.94USD vial
Rocephin 1 gm Solution Vial65.53USD vial
Rocephin 1 gm vial62.02USD vial
Duricef 500 mg/5ml Suspension 100ml Bottle59.36USD bottle
Cefzil 125 mg/5ml Suspension 100ml Bottle48.36USD bottle
Duricef 500 mg/5ml Suspension 75ml Bottle46.93USD bottle
Maxipime 2 gram vial43.04USD vial
Velosef 250 mg/5ml Suspension 100ml Bottle23.99USD bottle
Maxipime 1 gm piggyback vial23.24USD vial
Duricef 250 mg/5ml Suspension 50ml Bottle22.99USD bottle
Maxipime 1 gram vial21.7USD vial
Ceftin 500 mg tablet20.98USD tablet
Cefuroxime 1.5 g/50 ml bag16.8USD each
Cedax 400 mg capsule16.13USD each
Zinacef 1.5 gm add-vant vial13.94USD vial
Zinacef 1.5 gm vial13.45USD vial
Cefuroxime sod 1.5 gm vial13.44USD vial
Ceftin 250 mg tablet11.74USD tablet
Cefzil 500 mg tablet9.77USD tablet
Cefuroxime axetil 500 mg tablet8.11USD tablet
Duricef 1 gm tablet7.35USD tablet
Cefzil 250 mg tablet4.76USD tablet
Ceftin 500 mg Tablet3.61USD tablet
Cefuroxime axetil 250 mg tablet2.82USD tablet
Velosef 500 mg capsule2.02USD capsule
Apo-Cefuroxime 500 mg Tablet2.02USD tablet
Ratio-Cefuroxime 500 mg Tablet2.02USD tablet
Ceftin 250 mg Tablet1.82USD tablet
Velosef 250 mg capsule1.03USD capsule
Apo-Cefuroxime 250 mg Tablet1.02USD tablet
Ratio-Cefuroxime 250 mg Tablet1.02USD tablet
Zinacef-water 1.5 gm/50 ml0.32USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2408198No2004-03-092022-11-21Canada
CA1328405No1994-04-122011-04-12Canada

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)218-225 °CNot Available
water solubilityFreely soluble as sodium salt (145 mg/L)Not Available
logP-0.16SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.284 mg/mLALOGPS
logP-0.24ALOGPS
logP-0.9ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.76 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.17 m3·mol-1ChemAxon
Polarizability38.75 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6504
Blood Brain Barrier-0.9863
Caco-2 permeable-0.7051
P-glycoprotein substrateSubstrate0.7253
P-glycoprotein inhibitor INon-inhibitor0.8621
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8688
CYP450 2C9 substrateNon-substrate0.8686
CYP450 2D6 substrateNon-substrate0.8196
CYP450 3A4 substrateSubstrate0.5051
CYP450 1A2 substrateNon-inhibitor0.6957
CYP450 2C9 inhibitorNon-inhibitor0.7771
CYP450 2D6 inhibitorNon-inhibitor0.8707
CYP450 2C19 inhibitorNon-inhibitor0.7064
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8916
Ames testNon AMES toxic0.7525
CarcinogenicityNon-carcinogens0.8816
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity1.6593 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9724
hERG inhibition (predictor II)Non-inhibitor0.8292
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporin 3'-carbamates
Alternative Parents
N-acyl-alpha amino acids and derivatives / 1,3-thiazines / Tertiary carboxylic acid amides / Carbamate esters / Furans / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Organic carbonic acids and derivatives / Thiohemiaminal derivatives
show 10 more
Substituents
Cephalosporin 3'-carbamate / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Meta-thiazine / Furan / Heteroaromatic compound / Carbamic acid ester / Tertiary carboxylic acid amide / Azetidine / Carboxamide group
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxime O-ether, furans, 3-(carbamoyloxymethyl)cephalosporin (CHEBI:3515)

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring glycosyl groups
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
pbpA
Uniprot ID
Q8XJ01
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
75176.35 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Cornaglia G, Ligozzi M, Bauernfeind A, Satta G, Fontana R: PBP binding and periplasmic concentration as determinants of the antibacterial activities of three new oral cephalosporins in Escherichia coli. New Microbiol. 1994 Jul;17(3):203-10. [PubMed:7968655]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33