Identification

Name
Cefazolin
Accession Number
DB01327
Type
Small Molecule
Groups
Approved
Description

A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine. [PubChem]

Structure
Thumb
Synonyms
  • (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefamezin
  • Cefazolina
  • Cefazoline
  • Cefazolinum
  • Cephamezine
  • Cephazolidin
  • Cephazolin
  • Cephazoline
  • CEZ
External IDs
J01DB04
Product Ingredients
IngredientUNIICASInChI Key
Cefazolin sodiumP380M0454Z27164-46-1FLKYBGKDCCEQQM-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ancef Inj Pws 10gm/vial USPPowder, for solution10 gIntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1974-12-312000-07-25Canada
Ancef Inj Pws 1gm/vial USPPowder, for solution1 gIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1974-12-312000-12-15Canada
Ancef Inj Pws 500mg/vial USPPowder, for solution500 mgIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-312000-01-07Canada
CefazolinInjection, solution2 g/100mLIntravenousBaxter Laboratories2015-08-07Not applicableUs
Cefazolin for InjectionPowder, for solution0.5 gIntramuscular; IntravenousTeva1995-12-31Not applicableCanada
Cefazolin for InjectionPowder, for solution500 mgIntramuscular; IntravenousSterimax Inc2015-09-30Not applicableCanada
Cefazolin for InjectionPowder, for solution500 mgIntramuscular; IntravenousHospira, Inc.Not applicableNot applicableCanada
Cefazolin for InjectionPowder, for solution10 gIntravenousHospira, Inc.2008-07-26Not applicableCanada
Cefazolin for InjectionPowder, for solution10 gIntravenousSterimax Inc2015-06-11Not applicableCanada
Cefazolin for InjectionPowder, for solution1 gIntramuscular; IntravenousTeva1995-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CefazolinInjection, powder, for solution20 g/1IntravenousWest Ward Pharmaceutical2004-10-18Not applicableUs
CefazolinInjection, powder, for solution500 mg/2.2mLIntramuscular; IntravenousSagent Pharmaceuticals2009-02-01Not applicableUs
CefazolinPowder, for solution10 g/1IntravenousFresenius Kabi2011-06-14Not applicableUs
CefazolinInjection, powder, for solution1 g/3mLIntramuscular; IntravenousCardinal Health2005-10-07Not applicableUs
CefazolinInjection, powder, for solution500 mg/1Intramuscular; Intravenous; ParenteralSandoz1988-12-09Not applicableUs
CefazolinPowder1 g/gIntramuscular; IntravenousGeneral Injectables & Vaccines2010-07-012017-02-14Us
CefazolinInjection, powder, for solution10 g/1IntravenousSagent Pharmaceuticals2009-04-01Not applicableUs
CefazolinInjection, powder, for solution500 mg/2.2mLIntramuscular; IntravenousGeneral Injectables & Vaccines2017-02-15Not applicableUs
CefazolinInjection, powder, for solution1 g/1Intramuscular; IntravenousCardinal Health2012-04-20Not applicableUs
CefazolinInjection, powder, for solution1 g/3mLIntramuscular; IntravenousApotex Corporation2005-10-07Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefazolin SodiumInjection, solution2 g/100mLIntravenousCantrell Drug Company2011-11-01Not applicableUs
Cefazolin SodiumInjection, solution30 mg/mLIntravenousCantrell Drug Company2013-12-05Not applicableUs
Cefazolin SodiumInjection, solution100 mg/mLIntravenousCantrell Drug Company2013-10-11Not applicableUs
International/Other Brands
Ancef / Elzogram (Lilly) / Zolicef (Bristol-Myers Squibb)
Categories
UNII
IHS69L0Y4T
CAS number
25953-19-9
Weight
Average: 454.507
Monoisotopic: 454.030013046
Chemical Formula
C14H14N8O4S3
InChI Key
MLYYVTUWGNIJIB-BXKDBHETSA-N
InChI
InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
IUPAC Name
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][[email protected]]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[[email protected]]2NC(=O)CN1C=NN=N1)C(O)=O

Pharmacology

Indication

Mainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria. May be used for surgical prophylaxis; if required metronidazole may be added to cover B. fragilis.

Structured Indications
Pharmacodynamics

Cefazolin (also known as cefazoline or cephazolin) is a semi-synthetic first generation cephalosporin for parenteral administration. Cefazolin has broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.

Mechanism of action

In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. 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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1C
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 2
inhibitor
Escherichia coli (strain K12)
APeptidoglycan synthase FtsI
inhibitor
Escherichia coli (strain K12)
USerum paraoxonase/arylesterase 1
inhibitor
Human
Absorption

Not absorbed from GI tract. Must be administered parenterally. Peak serum concentrations attained 1-2 hours post intramuscular injection.

Volume of distribution
Not Available
Protein binding

74-86%

Metabolism

Not metabolized.

Route of elimination

Cefazolin is present in very low concentrations in the milk of nursing mothers. Cefazolin is excreted unchanged in the urine. In the first six hours approximately 60% of the drug is excreted in the urine and this increases to 70%-80% within 24 hours.

Half life

The serum half-life is approximately 1.8 hours following IV administration and approximately 2.0 hours following IM administration.

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

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolCefazolin may increase the anticoagulant activities of Acenocoumarol.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Cefazolin.Investigational
ClorindioneCefazolin may increase the anticoagulant activities of Clorindione.Experimental
DicoumarolCefazolin may increase the anticoagulant activities of Dicoumarol.Approved
DiphenadioneCefazolin may increase the anticoagulant activities of Diphenadione.Experimental
Ethyl biscoumacetateCefazolin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCefazolin may increase the anticoagulant activities of Fluindione.Investigational
FosphenytoinThe protein binding of Fosphenytoin can be decreased when combined with Cefazolin.Approved
PhenindioneCefazolin may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonCefazolin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe protein binding of Phenytoin can be decreased when combined with Cefazolin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefazolin.Approved
ProbenecidThe serum concentration of Cefazolin can be increased when it is combined with Probenecid.Approved
TeriflunomideThe serum concentration of Cefazolin can be increased when it is combined with Teriflunomide.Approved
TioclomarolCefazolin may increase the anticoagulant activities of Tioclomarol.Experimental
WarfarinCefazolin may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Michael Bornstein, Sandra M. Carone, "Method of preparing sterile essentially amorphous cefazolin for reconstitution for parenteral administration." U.S. Patent US4002748, issued August, 1967.

US4002748
General References
Not Available
External Links
Human Metabolome Database
HMDB15422
KEGG Drug
D02299
KEGG Compound
C06880
PubChem Compound
33255
PubChem Substance
46506123
ChemSpider
30723
BindingDB
50370587
ChEBI
474053
ChEMBL
CHEMBL1435
Therapeutic Targets Database
DAP000449
PharmGKB
PA448839
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cefazolin
ATC Codes
J01DB04 — Cefazolin
AHFS Codes
  • 08:12.06.04 — First Generation Cephalosporins
FDA label
Download (54.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentPremature Babies / Sepsis1
1CompletedTreatmentInfection NOS1
1RecruitingHealth Services ResearchBreast Implant Infection / Breast Reconstruction1
1Temporarily Not AvailableNot AvailableCellulitis / Diabetic Foot Ulcers (DFU) / Soft Tissues Infections / Wound Infections1
1, 2CompletedPreventionGeneral Surgery1
2CompletedTreatmentBacteremia1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
3CompletedPreventionArrythmias1
3CompletedPreventionCesarean Section / Infection NOS1
3CompletedPreventionLaryngeal Cancer1
3CompletedTreatmentNosocomial Neonatal Sepsis1
3CompletedTreatmentPreterm Premature Rupture of the Membranes1
3CompletedTreatmentTumors, Solid1
3Not Yet RecruitingPreventionBlood Antibiotic Levels1
3Not Yet RecruitingPreventionPeritoneal Dialysis Catheter Infection / Peritoneal dialysis complication / Peritoneal Dialysis-associated Peritonitis1
3RecruitingPreventionBone Neoplasms / Infection NOS1
3RecruitingTreatmentBacteremia1
3RecruitingTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA)1
3RecruitingTreatmentPreterm Premature Rupture of Membranes1
3RecruitingTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious1
3RecruitingTreatmentStaphylococcus Aureus Infections1
3TerminatedTreatmentBacteremia / Infections, Gram-Positive Bacterial1
3Unknown StatusTreatmentCellulitis1
4Active Not RecruitingPreventionArrythmias1
4CompletedBasic ScienceBMI >30 kg/m2 / Cesarean Delivery / Wound Infections1
4CompletedOtherPost-gastrointestinal bypass surgery1
4CompletedPreventionArrythmias1
4CompletedPreventionBMI >30 kg/m2 / Infection; Cesarean Section / Obesity, Morbid / Pregnancy1
4CompletedPreventionEmpyema / Pleural Effusions / Pleuritis1
4CompletedPreventionInfection, Postoperative Wound1
4CompletedPreventionInguinal Hernias1
4CompletedPreventionMRSA Infections1
4CompletedPreventionProphylaxis1
4CompletedTreatmentAnti-Infective Agents / Bacterial Infections / Breast Implantation1
4CompletedTreatmentBMI >30 kg/m21
4CompletedTreatmentOsteoarthritis (OA)1
4Not Yet RecruitingPreventionPostoperative Infections1
4RecruitingPreventionHepatocellular,Carcinoma1
4RecruitingPreventionPost Operative Wound Infection / Supracondylar Humerus Fractures1
4RecruitingPreventionSurgical Site Infections1
4RecruitingTreatmentAntibiotic Prophylaxis / Arthropathy of Knee1
4RecruitingTreatmentInfection, Postoperative Wound1
4Unknown StatusNot AvailableEndophthalmitis / Vitreoretinal Surgery1
4WithdrawnBasic ScienceAntibiotic Prophylaxis / Cesarean Delivery / Infection NOS1
4WithdrawnPreventionAcute Infection of Total Knee Replacement1
4WithdrawnPreventionEndometritis1
Not AvailableCompletedNot AvailableHepatic Cyst1
Not AvailableCompletedPreventionAntibiotic Prophylaxis / Breast-Conserving Surgery / Neoplasms, Breast / Wound Infections1
Not AvailableCompletedPreventionEndometritis / Wound Infections1
Not AvailableCompletedPreventionInfection Prevention1
Not AvailableCompletedPreventionInfection Rate After Fingertip Amputation1
Not AvailableCompletedPreventionInfection Secondary to Surgical Procedure1
Not AvailableCompletedPreventionOsteoarthritis (OA)1
Not AvailableCompletedPreventionProsthetic Joint Infection1
Not AvailableCompletedPreventionWound Infections1
Not AvailableCompletedTreatmentAntibiotic Prophylaxis1
Not AvailableCompletedTreatmentCervical Insufficiency1
Not AvailableCompletedTreatmentFractures, Closed / Wounds and Injuries1
Not AvailableCompletedTreatmentPlasma Concentration of Antibiotics1
Not AvailableEnrolling by InvitationPreventionFractures, Closed / Infection NOS1
Not AvailableRecruitingPreventionAntibiotic Prophylaxis / Thoracic Surgery1
Not AvailableRecruitingPreventionPropionibacterium infection1
Not AvailableRecruitingPreventionSurgical Site Infections1
Not AvailableRecruitingTreatmentBacterial Keratitis1
Not AvailableRecruitingTreatmentCancer, Breast1
Not AvailableRecruitingTreatmentKnee Arthropathy1
Not AvailableUnknown StatusPreventionDentofacial Deformity1
Not AvailableUnknown StatusPreventionHysterectomy1
Not AvailableUnknown StatusTreatmentPeritonitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
InjectionIntramuscular500 mg/10mL
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/3mL
Injection, powder, for solutionIntramuscular; Intravenous225 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous330 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous500 mg/500mg
Injection, powder, for solutionIntramuscular; Intravenous500 mg/1
Injection, powder, for solutionIntramuscular; Intravenous500 mg/2.2mL
Injection, powder, for solutionIntramuscular; Intravenous; Parenteral1 g/1
Injection, powder, for solutionIntramuscular; Intravenous; Parenteral500 mg/1
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous10 g/1
Injection, powder, for solutionIntravenous20 g/100mL
Injection, powder, for solutionIntravenous20 g/1
Injection, powder, for solutionIntravenous; Parenteral10 g/1
Injection, powder, lyophilized, for solutionIntravenous100 g/1
Injection, powder, lyophilized, for solutionIntravenous300 g/1
Injection, solutionIntravenous1 g/50mL
PowderIntramuscular; Intravenous1 g/g
Powder, for solutionIntramuscular; Intravenous1 g/3mL
Powder, for solutionIntramuscular; Intravenous500 mg/2.2mL
Powder, for solutionIntravenous10 g/1
Powder, for solutionIntravenous20 g/100mL
Powder, for solutionIntramuscular; Intravenous0.5 g
Powder, for solutionIntramuscular; Intravenous1 g
Powder, for solutionIntravenous10 g
Powder, for solutionIntramuscular; Intravenous10 g
Powder, for solutionIntramuscular; Intravenous20 g
Powder, for solutionIntramuscular; Intravenous1.0 g
Powder, for solutionIntramuscular; Intravenous500 mg
Powder, for solutionIntravenous100 g
Powder, for solutionIntravenous20 g
Injection, solutionIntravenous100 mg/mL
Injection, solutionIntravenous2 g/100mL
Injection, solutionIntravenous30 mg/mL
SolutionIntravenous1 g/50mL
SolutionIntravenous2 g/50mL
Powder, for solutionIntravenous1 g
Powder, for solutionIntravenous500 mg
Prices
Unit descriptionCostUnit
Cefazolin 10 g/vial58.66USD vial
Sterile Cefazolin Sodium 10 g/vial58.66USD vial
Cefazolin 20 gm bulk vial29.69USD vial
Cefazolin 10 gm vial24.0USD vial
Cefazolin 1 g/vial6.29USD vial
Sterile Cefazolin Sodium 1 g/vial6.29USD vial
Cefazolin 1 gm-d5w bag5.04USD each
Cefazolin 500 mg/vial4.19USD vial
Sterile Cefazolin Sodium 500 mg/vial4.19USD vial
Cefazolin 1 gm vial3.12USD vial
Cefazolin sod 100 gm bulk bag1.26USD g
Cefazolin sod-water 1 g/10 ml0.93USD ml
Cefazolin-d5w 2 g/100 ml0.17USD ml
Cefazolin-ns 2 g/100 ml0.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-0.58HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.487 mg/mLALOGPS
logP-0.4ALOGPS
logP-1.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)0.26ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area156.09 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.86 m3·mol-1ChemAxon
Polarizability41.44 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5119
Blood Brain Barrier-0.987
Caco-2 permeable-0.7891
P-glycoprotein substrateSubstrate0.7863
P-glycoprotein inhibitor INon-inhibitor0.8663
P-glycoprotein inhibitor IINon-inhibitor0.9603
Renal organic cation transporterNon-inhibitor0.8574
CYP450 2C9 substrateNon-substrate0.7588
CYP450 2D6 substrateNon-substrate0.818
CYP450 3A4 substrateNon-substrate0.5161
CYP450 1A2 substrateNon-inhibitor0.8949
CYP450 2C9 inhibitorNon-inhibitor0.8746
CYP450 2D6 inhibitorNon-inhibitor0.9178
CYP450 2C19 inhibitorNon-inhibitor0.8363
CYP450 3A4 inhibitorNon-inhibitor0.9377
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6362
Ames testNon AMES toxic0.6675
CarcinogenicityNon-carcinogens0.8876
BiodegradationNot ready biodegradable0.7464
Rat acute toxicity2.2215 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8898
hERG inhibition (predictor II)Non-inhibitor0.8711
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05fr-0109500000-d35195620e6ac4356773
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aba-0943000000-da64d40a841f7fe440fe
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zfr-0910000000-f074c2d1d56b5f3da552
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0q2i-0900000000-bbd7d226d641cfe51521
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0l1r-0900000000-18addd569fa36108660e

Taxonomy

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 / Alkylarylthioethers / 1,3-thiazines / Thiadiazoles / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives
show 10 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Aryl thioether / Alkylarylthioether / Meta-thiazine / Azole / Heteroaromatic compound / Tertiary carboxylic acid amide / Tetrazole
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:474053) / Cephems (C06880)

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
mrcA
Uniprot ID
P02918
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
93635.545 Da
References
  1. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730]
  2. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [PubMed:2722720]
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. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [PubMed:2722720]
  2. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Cell wall formation. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a transpeptidase C-terminal domain which may not be functional.
Gene Name
pbpC
Uniprot ID
P76577
Uniprot Name
Penicillin-binding protein 1C
Molecular Weight
85066.085 Da
References
  1. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [PubMed:2722720]
  2. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730]
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
  1. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [PubMed:2722720]
  2. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730]
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
  1. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [PubMed:2722720]
  2. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxyl...
Gene Name
PON1
Uniprot ID
P27169
Uniprot Name
Serum paraoxonase/arylesterase 1
Molecular Weight
39730.99 Da
References
  1. Sinan S, Kockar F, Arslan O: Novel purification strategy for human PON1 and inhibition of the activity by cephalosporin and aminoglikozide derived antibiotics. Biochimie. 2006 May;88(5):565-74. Epub 2006 Jan 19. [PubMed:16600468]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Thiopurine s-methyltransferase activity
Specific Function
Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name
TPMT
Uniprot ID
P51580
Uniprot Name
Thiopurine S-methyltransferase
Molecular Weight
28180.09 Da
References
  1. Kerremans AL, Lipsky JJ, Van Loon J, Gallego MO, Weinshilboum RM: Cephalosporin-induced hypoprothrombinemia: possible role for thiol methylation of 1-methyltetrazole-5-thiol and 2-methyl-1,3,4-thiadiazole-5-thiol. J Pharmacol Exp Ther. 1985 Nov;235(2):382-8. [PubMed:2865352]
  2. Wood TC, Johnson KL, Naylor S, Weinshilboum RM: Cefazolin administration and 2-methyl-1,3,4-thiadiazole-5-thiol in human tissue: possible relationship to hypoprothrombinemia. Drug Metab Dispos. 2002 Oct;30(10):1123-8. [PubMed:12228189]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216]
  2. Decroix MO, Zini R, Chaumeil JC, Tillement JP: Cefazolin serum protein binding and its inhibition by bilirubin, fatty acids and other drugs. Biochem Pharmacol. 1988 Jul 15;37(14):2807-14. [PubMed:3395358]
  3. Ichimura F, Matsushita R, Tsuji A, Deguchi Y: Mutual interaction between bilirubin and cefazolin in binding to human serum albumin. J Pharm Sci. 1990 Nov;79(11):1041-2. [PubMed:2292768]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Ci L, Kusuhara H, Adachi M, Schuetz JD, Takeuchi K, Sugiyama Y: Involvement of MRP4 (ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney. Mol Pharmacol. 2007 Jun;71(6):1591-7. Epub 2007 Mar 7. [PubMed:17344354]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
  2. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
  3. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172]
  4. Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [PubMed:15618660]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172]
  3. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [PubMed:12358729]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]

Drug created on June 30, 2007 11:22 / Updated on November 19, 2017 20:33