Cefazolin

Identification

Summary

Cefazolin is a broad-spectrum cephalosporin antibiotic mainly used for the treatment of skin bacterial infections and other moderate to severe bacterial infections in the lung, bone, joint, stomach, blood, heart valve, and urinary tract.

Generic Name
Cefazolin
DrugBank Accession Number
DB01327
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 454.507
Monoisotopic: 454.030013046
Chemical Formula
C14H14N8O4S3
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
  • Cefazolin
  • Cefazolina
  • Cefazoline
  • Cefazolinum
  • Cephamezine
  • Cephazolidin
  • Cephazolin
  • Cephazoline
  • CEZ
External IDs
  • J01DB04

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBacterial septicemia caused by susceptible bacterial infections•••••••••••••••••••••
Treatment ofBiliary tract infection bacterial caused by susceptible bacterial infections•••••••••••••••••••••
Treatment ofBone and joint infections caused by susceptible bacterial infections•••••••••••••••••••••
Treatment ofCommunity acquired pneumonia••• ••••••••••••••
Treatment ofEndocarditis caused by susceptible bacterial infections•••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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
Humans
UInterleukin-15
inhibitor
Humans
UInterleukin-2
inhibitor
Humans
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

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
AbacavirCefazolin 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 Cefazolin.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Cefazolin.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cefazolin is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefazolin is combined with Acemetacin.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cefazolin sodiumP380M0454Z27164-46-1FLKYBGKDCCEQQM-WYUVZMMLSA-M
International/Other Brands
Elzogram (Lilly) / Zolicef (Bristol-Myers Squibb)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AncefInjection10 g/1IntramuscularGlaxoSmithKline2005-12-142005-12-14US flag
AncefInjection1 g/1IntramuscularGlaxosmithkline Inc2006-02-032011-02-11US flag
AncefInjection1 g/1IntramuscularGlaxoSmithKline2005-12-142005-12-14US flag
Ancef Inj Pws 10gm/vial USPPowder, for solution10 g / vialIntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1974-12-312000-07-25Canada flag
Ancef Inj Pws 1gm/vial USPPowder, for solution1 g / vialIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1974-12-312000-12-15Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CefazolinPowder, for solution10 g/1IntravenousFresenius Kabi USA, LLC2011-06-14Not applicableUS flag
CefazolinInjection, powder, for solution1 g/1IntravenousWG Critical Care, LLC2012-04-182012-04-18US flag
CefazolinInjection, powder, for solution225 mg/1mLIntramuscular; IntravenousGeneral Injectables & Vaccines, Inc.2019-12-302024-11-30US flag
CefazolinInjection, powder, for solution10 g/1IntravenousWG Critical Care, LLC2015-03-06Not applicableUS flag
CefazolinInjection, powder, for solution1 g/3mLIntramuscular; IntravenousApotex Corporation2005-10-072016-11-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CEFAMEZIN 1000 MG IM STERİL ENJEKTABL TOZ İÇEREN FLAKON, 1 ADETCefazolin sodium (1000 mg) + Lidocaine hydrochloride (0.5 %)Injection, powder, for solutionIntramuscularSANOFİ İLAÇ SAN. VE TİC. A.Ş.2008-03-272022-09-12Turkey flag
CEFAMEZIN 250 MG IM ENJEKTABL TOZ İÇEREN FLAKON, 1 ADETCefazolin sodium (250 mg) + Lidocaine hydrochloride (0.5 %)Injection, powder, for solutionIntramuscularSANOFİ İLAÇ SAN. VE TİC. A.Ş.2008-03-272022-09-12Turkey flag
CEFAMEZIN 500 MG IM ENJEKTABL TOZ İÇEREN FLAKON, 1 ADETCefazolin sodium (500 mg) + Lidocaine hydrochloride (0.5 %)Injection, powder, for solutionIntramuscularSANOFİ İLAÇ SAN. VE TİC. A.Ş.2008-03-272022-09-12Turkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Cefazolin SodiumCefazolin sodium (100 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2013-11-14Not applicableUS flag
Cefazolin SodiumCefazolin sodium (2 g/100mL)Injection, solutionIntravenousCantrell Drug Company2011-09-302015-01-14US flag
Cefazolin SodiumCefazolin sodium (2 g/100mL)Injection, solutionIntravenousCantrell Drug Company2011-11-01Not applicableUS flag
Cefazolin SodiumCefazolin sodium (30 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2013-12-05Not applicableUS flag

Categories

ATC Codes
J01DB04 — Cefazolin
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 / Alkylarylthioethers / 1,3-thiazines / Thiadiazoles / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives
show 10 more
Substituents
Alkylarylthioether / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Carbonyl group / Carboxamide group / Carboxylic acid
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:474053) / Cephems (C06880)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
IHS69L0Y4T
CAS number
25953-19-9
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][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O

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
Human Metabolome Database
HMDB0015422
KEGG Drug
D02299
KEGG Compound
C06880
PubChem Compound
33255
PubChem Substance
46506123
ChemSpider
30723
BindingDB
50370587
RxNav
2180
ChEBI
474053
ChEMBL
CHEMBL1435
ZINC
ZINC000003830405
Therapeutic Targets Database
DAP000449
PharmGKB
PA448839
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cefazolin
FDA label
Download (54.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionSurgical Site Infections1
4CompletedBasic ScienceBurns / Surgery / Wound Infections1
4CompletedBasic ScienceCesarean Delivery / Obesity / Wound Infections1
4CompletedOtherPost-gastrointestinal bypass surgery1
4CompletedPreventionAortic Valve Disorder / Congenital Heart Disease (CHD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Antibioticos Ltd.
  • Apotex Inc.
  • APP Pharmaceuticals
  • Aurobindo Pharma Ltd.
  • B. Braun Melsungen AG
  • Baxter International Inc.
  • BMH Ltd.
  • Cardinal Health
  • Cephazone Pharma LLC
  • Cura Pharmaceutical Co. Inc.
  • Dispensing Solutions
  • Eli Lilly & Co.
  • GC Hanford Manufacturing Co.
  • GlaxoSmithKline Inc.
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Mead Johnson and Co.
  • Orchid Healthcare
  • Pfizer Animal Health
  • Pfizer Inc.
  • Pharmakon
  • Pharmedium
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Ranbaxy Laboratories
  • Sagent Pharmaceuticals
  • Samson Medical Technologies
  • Sandoz
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
InjectionIntramuscular1 g/1
InjectionIntramuscular10 g/1
Injection1 G
Injection250 MG
Injection500 MG
Injection, powder, for solutionIntramuscular250 MG
Injection, powder, for solutionIntramuscular500 MG
Injection, powder, for solutionIntramuscular; Parenteral1000 MG/4ML
Injection, powder, for solutionIntramuscular; Parenteral250 MG/2ML
Injection, powder, for solutionIntramuscular; Parenteral500 MG/2ML
Injection, powder, for solutionIntravenous; Parenteral1000 MG/10ML
Injection, powder, for solutionIntramuscular
InjectionIntramuscular; Intravenous1000 mg
Injection, powder, for solutionIntramuscular1 g
InjectionIntramuscular1 g/100mL
InjectionIntramuscular500 mg/10mL
InjectionIntravenous500 mg/50mL
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/3mL
Injection, powder, for solutionIntramuscular; Intravenous2 g/1
Injection, powder, for solutionIntramuscular; Intravenous225 mg/1mL
Injection, powder, for solutionIntramuscular; Intravenous3 g/1
Injection, powder, for solutionIntramuscular; Intravenous330 mg/1mL
Injection, powder, for solutionIntramuscular; Intravenous500 mg/10mL
Injection, powder, for solutionIntramuscular; Intravenous500 mg/2.2mL
Injection, powder, for solutionIntramuscular; Intravenous500 mg/1
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 solutionIntravenous1 g/5mL
Injection, powder, for solutionIntravenous10 g/1
Injection, powder, for solutionIntravenous2 g/1
Injection, powder, for solutionIntravenous20 g/1
Injection, powder, for solutionIntravenous20 g/100mL
Injection, powder, for solutionIntravenous3 g/1
Injection, powder, for solutionIntravenous500 mg/1
Injection, powder, for solutionIntravenous; Parenteral10 g/1
Injection, powder, lyophilized, for solutionIntramuscular1 g/1
Injection, powder, lyophilized, for solutionIntravenous100 g/1
Injection, powder, lyophilized, for solutionIntravenous2 g/1
Injection, powder, lyophilized, for solutionIntravenous300 g/1
Injection, solutionIntravenous1 g/50mL
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; Intravenous1 g / vial
Powder, for solutionIntramuscular; Intravenous500 mg / vial
Powder, for solutionIntravenous10 g / vial
Powder, for solutionIntramuscular; Intravenous20 g / vial
Injection, powder, for solutionIntramuscular; Intravenous1 g
Powder, for solutionIntramuscular; Intravenous1.0 g / vial
Powder, for solutionIntravenous100 g / bag
Powder, for solutionIntravenous20 g / vial
SolutionIntravenous20 mg / mL
Injection, powder, for solutionIntramuscular; Intravenous1 g/vial
Injection, powder, for solutionIntravenous
Injection, powder, for solutionParenteral0.5 g
Injection, solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral2 g
Injection, powder, for solution
Injection, powder, for solution1 g
Injection, solutionIntravenous100 mg/1mL
Injection, solutionIntravenous2 g/100mL
Injection, solutionIntravenous30 mg/1mL
SolutionIntravenous1 g/50mL
SolutionIntravenous2 g/50mL
Powder, for solutionIntramuscular; Intravenous2 g / vial
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous1 g
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous500 MG
Injection, powder, for solutionIntravenous
PowderIntramuscular
Injection, powder, for solutionIntramuscular; Parenteral1 G/4ML
Injection, powder, for solutionIntramuscular; Parenteral500 MG/3ML
Injection, powder, for solutionIntravenous; Parenteral1 G/10ML
Injection, powder, for solution2 G
Injection, powder, lyophilized, for solutionParenteral1 g
Injection, powder, for solutionIntravenous250 MG
Injection, powder, for solutionIntravenous500 MG
Injection, powder, for solutionParenteral1 G
Injection, powder, for solutionParenteral500 MG
Injection, solutionIntramuscular1 g
InjectionIntramuscular250 mg
InjectionIntramuscular500 mg
InjectionIntramuscular; Intravenous1 g
InjectionIntramuscular1 g
Injection, powder, for solutionIntramuscular; Intravenous1 gm
Injection, powder, for solution1 G/4ML
Injection, powder, for solutionIntramuscular; Intravenous1 gr
Injection, powder, for solutionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Powder, for solutionIntravenous1 g / vial
Powder, for solutionIntravenous500 mg / vial
Injection, powder, for solutionIntramuscular1000 mg
InjectionIntramuscular; Intravenous
InjectionIntramuscular1000 mg
InjectionIntramuscular; Intravenous250 mg
InjectionIntramuscular; Intravenous500 mg
Injection, powder, for solutionParenteral
Powder, for solutionIntramuscular; Intravenous10 g / vial
Injection
Injection, powder, for solutionIntramuscular
Powder, for solution
Injection, powder, for solutionIntramuscular; Intravenous1000 mg
Injection, powder, for solutionIntramuscular; Intravenous100000 g
PowderIntramuscular250 mg/1vial
PowderIntramuscular500 mg/1vial
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)2.84Chemaxon
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
Polarizability41.57 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-MSsplash10-05ai-9331300000-a190d4fa6f7addfc7f8c
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0201900000-a701726f9203a77dcaf9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0v00-1500900000-bfb4930f73bb68879471
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0400900000-9145e2cdfaf49a388739
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-003s-9300000000-2820e36bf0cb57da0c15
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-1654900000-edd5fec39ce4a9db9401
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9600200000-037df95967cca9c3836f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.3584403
predicted
DarkChem Lite v0.1.0
[M-H]-211.5077403
predicted
DarkChem Lite v0.1.0
[M-H]-190.89812
predicted
DeepCCS 1.0 (2019)
[M+H]+197.8430403
predicted
DarkChem Lite v0.1.0
[M+H]+210.5621403
predicted
DarkChem Lite v0.1.0
[M+H]+193.25612
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.8967403
predicted
DarkChem Lite v0.1.0
[M+Na]+210.4873403
predicted
DarkChem Lite v0.1.0
[M+Na]+199.77559
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Cytokine activity
Specific Function
Cytokine that stimulates the proliferation of T-lymphocytes. Stimulation by IL-15 requires interaction of IL-15 with components of IL-2R, including IL-2R beta and probably IL-2R gamma but not IL-2R...
Gene Name
IL15
Uniprot ID
P40933
Uniprot Name
Interleukin-15
Molecular Weight
18085.655 Da
References
  1. Zyzynska-Granica B, Trzaskowski B, Niewieczerzal S, Filipek S, Zegrocka-Stendel O, Dutkiewicz M, Krzeczynski P, Kowalewska M, Koziak K: Pharmacophore guided discovery of small-molecule interleukin 15 inhibitors. Eur J Med Chem. 2017 Aug 18;136:543-547. doi: 10.1016/j.ejmech.2017.05.034. Epub 2017 May 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Kinase activator activity
Specific Function
Produced by T-cells in response to antigenic or mitogenic stimulation, this protein is required for T-cell proliferation and other activities crucial to regulation of the immune response. Can stimu...
Gene Name
IL2
Uniprot ID
P60568
Uniprot Name
Interleukin-2
Molecular Weight
17627.52 Da
References
  1. Zyzynska-Granica B, Trzaskowski B, Niewieczerzal S, Filipek S, Zegrocka-Stendel O, Dutkiewicz M, Krzeczynski P, Kowalewska M, Koziak K: Pharmacophore guided discovery of small-molecule interleukin 15 inhibitors. Eur J Med Chem. 2017 Aug 18;136:543-547. doi: 10.1016/j.ejmech.2017.05.034. Epub 2017 May 12. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Carriers

Kind
Protein
Organism
Humans
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. doi: 10.1159/000136629. [Article]
  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. [Article]
  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. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 30, 2007 17:22 / Updated at March 18, 2024 16:48