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Identification
NameCefazolin
Accession NumberDB01327
TypeSmall Molecule
GroupsApproved
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 Identifiers Not Available
Approved 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 Healthcare Corporation2015-08-31Not applicableUs
Cefazolin for Injectionpowder for solution1 gintramuscular; intravenousHospira Healthcare Corporation2008-07-26Not applicableCanada
Cefazolin for Injectionpowder for solution10 gintravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Cefazolin for Injectionpowder for solution1 gintramuscular; intravenousSterimax Inc2015-09-29Not applicableCanada
Cefazolin for Injectionpowder for solution500 mgintramuscular; intravenousSterimax Inc2015-09-30Not applicableCanada
Cefazolin for Injectionpowder for solution10 gintravenousTeva Canada Limited1995-12-31Not applicableCanada
Cefazolin for Injectionpowder for solution500 mgintramuscular; intravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Cefazolin for Injectionpowder for solution1 gintramuscular; intravenousTeva Canada Limited1995-12-31Not applicableCanada
Cefazolin for Injectionpowder for solution0.5 gintramuscular; intravenousTeva Canada Limited1995-12-31Not applicableCanada
Cefazolin for Injectionpowder for solution10 gintravenousSterimax Inc2015-06-11Not applicableCanada
Cefazolin for Injectionpowder for solution10 gintravenousHospira Healthcare Corporation2008-07-26Not applicableCanada
Cefazolin for Injection USPpowder for solution20 gintramuscular; intravenousNovopharm LimitedNot applicableNot applicableCanada
Cefazolin for Injection USPpowder for solution10 gintramuscular; intravenousSandoz Canada Incorporated2008-04-18Not applicableCanada
Cefazolin for Injection USPpowder for solution1 gintramuscular; intravenousSandoz Canada Incorporated2008-04-18Not applicableCanada
Cefazolin for Injection USPpowder for solution500 mgintramuscular; intravenousSandoz Canada Incorporated2008-04-18Not applicableCanada
Cefazolin for Injection, USPpowder for solution20 gintravenousFresenius Kabi Canada Ltd1998-10-30Not applicableCanada
Cefazolin for Injection, USPpowder for solution500 mgintramuscular; intravenousFresenius Kabi Canada Ltd1998-10-30Not applicableCanada
Cefazolin for Injection, USPpowder for solution100 gintravenousFresenius Kabi Canada Ltd2013-06-03Not applicableCanada
Cefazolin for Injection, USPpowder for solution10 gintravenousFresenius Kabi Canada Ltd1998-10-30Not applicableCanada
Cefazolin for Injection, USPpowder for solution1.0 gintramuscular; intravenousFresenius Kabi Canada Ltd1998-10-30Not applicableCanada
Cefazolin Sodiumsolution1 g/50mLintravenousB. Braun Medical Inc.2000-07-27Not applicableUs
Cefazolin Sodiumsolution2 g/50mLintravenousB. Braun Medical Inc.2012-01-13Not applicableUs
Kefzolpowder for solution1 gintramuscular; intravenousPharmaceutical Partners Of Canada Inc1975-12-312008-02-13Canada
Kefzolpowder for solution500 mgintramuscular; intravenousPharmaceutical Partners Of Canada Inc1975-12-312008-02-13Canada
Kefzolpowder for solution10 gintravenousPharmaceutical Partners Of Canada Inc1984-12-312008-02-13Canada
Kefzol Add-vantage Inj 1gm/vialpowder for solution1 gintravenousEli Lilly Canada Inc1988-12-311999-09-13Canada
Kefzol Add-vantage Inj 500mg/vialpowder for solution500 mgintravenousEli Lilly Canada Inc1988-12-311998-08-04Canada
Sterile Cefazolin Sodiumpowder for solution10 gintramuscular; intravenousTeva Pharmaceutical Industries LtdNot applicableNot applicableCanada
Sterile Cefazolin Sodiumpowder for solution1 gintramuscular; intravenousTeva Pharmaceutical Industries LtdNot applicableNot applicableCanada
Sterile Cefazolin Sodiumpowder for solution500 mgintramuscular; intravenousTeva Pharmaceutical Industries LtdNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefazolinpowder, for solution1 g/3mLintramuscular; intravenousFresenius Kabi USA, LLC2011-07-15Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenousCardinal Health2005-10-07Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenousWG Critical Care, LLC2015-03-06Not applicableUs
Cefazolinpowder1 g/gintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-07-01Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenous; parenteralSandoz Inc1988-12-09Not applicableUs
Cefazolininjection, powder, for solution20 g/1intravenousWest ward Pharmaceutical Corp2004-10-18Not applicableUs
Cefazolininjection, powder, for solution1 g/3mLintramuscular; intravenousApotex Corporation2005-10-07Not applicableUs
Cefazolinpowder, for solution10 g/1intravenousFresenius Kabi USA, LLC2011-06-14Not applicableUs
Cefazolinpowder, for solution500 mg/2.2mLintramuscular; intravenousFresenius Kabi USA, LLC2011-07-15Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenous; parenteralCardinal Health1988-12-09Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenousWG Critical Care, LLC2015-03-06Not applicableUs
Cefazolininjection, powder, for solution500 mg/1intramuscular; intravenous; parenteralSandoz Inc1988-12-09Not applicableUs
Cefazolininjection, powder, for solution1 g/1intravenousHospira, Inc.2009-03-24Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenousApotex Corp2005-10-072016-03-16Us
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenous; parenteralCardinal Health1988-12-09Not applicableUs
Cefazolininjection, powder, for solution500 mg/1intramuscular; intravenousWG Critical Care, LLC2015-03-06Not applicableUs
Cefazolininjection, powder, for solution1 g/1intravenousHospira, Inc2007-05-09Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenousQilu Pharmaceutical Co., Ltd.2015-12-28Not applicableUs
Cefazolininjection, powder, for solution500 mg/1intramuscular; intravenousApotex Corp2005-10-072016-03-16Us
Cefazolininjection, powder, for solution1 g/1intravenousCardinal Health2007-05-09Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenousSagent Pharmaceuticals2009-04-01Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenousHospira, Inc.2009-03-24Not applicableUs
Cefazolininjection, powder, for solution1 g/3mLintramuscular; intravenousDispensing Solutions, Inc.2009-02-01Not applicableUs
Cefazolinpowder, for solution1 g/3mLintramuscular; intravenousCardinal Health2011-07-15Not applicableUs
Cefazolininjection500 mg/10mLintramuscularPhysicians Total Care, Inc.2003-09-15Not applicableUs
Cefazolininjection, powder, for solution1 g/3mLintramuscular; intravenousSagent Pharmaceuticals2009-02-01Not applicableUs
Cefazolininjection, solution1 g/50mLintravenousBaxter Healthcare Corporation1991-03-28Not applicableUs
Cefazolininjection, powder, lyophilized, for solution300 g/1intravenousSamson Medical Technologies, L.L.C.2007-01-01Not applicableUs
Cefazolininjection, powder, for solution500 mg/500mgintramuscular; intravenousGeneral Injectables & Vaccines, Inc.2010-03-01Not applicableUs
Cefazolininjection, powder, for solution500 mg/2.2mLintramuscular; intravenousSagent Pharmaceuticals2009-02-01Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenousWest ward Pharmaceutical Corp2004-10-18Not applicableUs
Cefazolininjection, powder, lyophilized, for solution100 g/1intravenousSamson Medical Technologies, L.L.C.2007-01-01Not applicableUs
Cefazolininjection, powder, for solution1 g/3mLintramuscular; intravenousCardinal Health2009-03-24Not applicableUs
Cefazolininjection1 g/1intramuscular; intravenousCardinal Health2001-09-18Not applicableUs
Cefazolininjection, powder, for solution500 mg/500mgintramuscular; intravenousGeneral Injectables & Vaccines, Inc2012-04-12Not applicableUs
Cefazolininjection, powder, for solution500 mg/1intramuscular; intravenous; parenteralSandoz Inc1988-12-09Not applicableUs
Cefazolininjection, powder, for solution330 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2001-09-18Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenousApotex Corporation2012-04-20Not applicableUs
Cefazolinpowder, for solution20 g/100mLintravenousFresenius Kabi USA, LLC2011-06-14Not applicableUs
Cefazolininjection, powder, for solution1 g/1intramuscular; intravenousCardinal Health2012-04-20Not applicableUs
Cefazolininjection, powder, for solution1 g/3mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2011-09-07Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenous; parenteralSandoz Inc1988-12-09Not applicableUs
Cefazolininjection, powder, for solution225 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2001-09-18Not applicableUs
Cefazolininjection, powder, for solution10 g/1intravenousApotex Corporation2006-06-132016-04-05Us
Cefazolininjection, powder, for solution20 g/100mLintravenousAPP Pharmaceuticals, LLC2012-07-13Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefazolin Sodiuminjection, solution2 g/100mLintravenousCantrell Drug Company2011-11-01Not applicableUs
Cefazolin Sodiuminjection, solution100 mg/mLintravenousCantrell Drug Company2013-10-11Not applicableUs
Cefazolin Sodiuminjection, solution30 mg/mLintravenousCantrell Drug Company2013-12-05Not applicableUs
International Brands
NameCompany
AncefNot Available
ElzogramLilly
ZolicefBristol-Myers Squibb
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefazolin sodium
27164-46-1
Thumb
  • InChI Key: FLKYBGKDCCEQQM-WYUVZMMLSA-M
  • Monoisotopic Mass: 476.011957689
  • Average Mass: 476.489
DBSALT000310
Categories
UNIIIHS69L0Y4T
CAS number25953-19-9
WeightAverage: 454.507
Monoisotopic: 454.030013046
Chemical FormulaC14H14N8O4S3
InChI KeyInChIKey=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][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[[email protected]]2NC(=O)CN1C=NN=N1)C(O)=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • Meta-thiazine
  • Heteroaromatic compound
  • Thiadiazole
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationMainly 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.
PharmacodynamicsCefazolin (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 actionIn 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.
Related Articles
AbsorptionNot absorbed from GI tract. Must be administered parenterally. Peak serum concentrations attained 1-2 hours post intramuscular injection.
Volume of distributionNot Available
Protein binding74-86%
Metabolism

Not metabolized.

Route of eliminationCefazolin 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 lifeThe serum half-life is approximately 1.8 hours following IV administration and approximately 2.0 hours following IM administration.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injectionintramuscular500 mg/10mL
Injectionintramuscular; intravenous1 g/1
Injection, powder, for solutionintramuscular; intravenous1 g/3mL
Injection, powder, for solutionintramuscular; intravenous1 g/1
Injection, powder, for solutionintramuscular; intravenous225 mg/mL
Injection, powder, for solutionintramuscular; intravenous330 mg/mL
Injection, powder, for solutionintramuscular; intravenous500 mg/1
Injection, powder, for solutionintramuscular; intravenous500 mg/2.2mL
Injection, powder, for solutionintramuscular; intravenous500 mg/500mg
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
Injection, solutionintravenous2 g/100mL
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, 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.
PatentsNot Available
Properties
StateSolid
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferencesNot Available
External Links
ATC CodesJ01DB04
AHFS Codes
  • 08:12.06.04
PDB EntriesNot Available
FDA labelDownload (54.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolCefazolin may increase the anticoagulant activities of Acenocoumarol.
DicoumarolCefazolin may increase the anticoagulant activities of Dicoumarol.
FosphenytoinThe protein binding of Fosphenytoin can be decreased when combined with Cefazolin.
PhenytoinThe protein binding of Phenytoin can be decreased when combined with Cefazolin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Cefazolin.
ProbenecidThe serum concentration of Cefazolin can be increased when it is combined with Probenecid.
WarfarinCefazolin may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:
mrcA
Uniprot ID:
P02918
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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:
mrcB
Uniprot ID:
P02919
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
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
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 from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:
ftsI
Uniprot ID:
P0AD68
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 carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
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
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
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
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
substrateinhibitor
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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
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 ]
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Drug created on June 30, 2007 11:22 / Updated on September 16, 2013 17:14