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
Structure for Cefazolin (DB01327)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Bacterial Septicemia caused by susceptible Bacterial Infections
- Biliary tract infection bacterial caused by susceptible Bacterial Infections
- Bone and Joint Infections caused by susceptible Bacterial Infections
- Catheter-related Bloodstream Infection (CRBSI) NOS
- Community Acquired Pneumonia (CAP)
- Endocarditis caused by susceptible Bacterial Infections
- Genital infection caused by susceptible Bacterial Infections
- Osteoarticular Infections
- Postoperative Infections
- Respiratory Tract Infection Bacterial caused by susceptible Bacterial Infections
- Skin and Soft Tissue Infections (SSTIs)
- Skin and Subcutaneous Tissue Infection caused by susceptible Bacterial Infections
- Susceptible infections
- Urinary Tract Infection caused by susceptible Bacterial Infections
- Perioperative infection
- Susceptible Bacterial Infections
- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1C inhibitorEscherichia coli (strain K12) APenicillin-binding protein 2 inhibitorEscherichia coli (strain K12) APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) USerum paraoxonase/arylesterase 1 inhibitorHumans UInterleukin-15 inhibitorHumans UInterleukin-2 inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cefazolin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefazolin. Acamprosate The excretion of Acamprosate can be decreased when combined with Cefazolin. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefazolin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefazolin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefazolin is combined with Acenocoumarol. Acetaminophen Cefazolin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide The excretion of Cefazolin can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Cefazolin can be decreased when combined with Acetylsalicylic acid. Aclidinium Cefazolin may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefazolin sodium P380M0454Z 27164-46-1 FLKYBGKDCCEQQM-WYUVZMMLSA-M - International/Other Brands
- Elzogram (Lilly) / Zolicef (Bristol-Myers Squibb)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ancef Injection 10 g/1 Intramuscular GlaxoSmithKline 2005-12-14 2005-12-14 US 
Ancef Injection 1 g/1 Intramuscular Glaxosmithkline Inc 2006-02-03 2011-02-11 US Ancef Injection 1 g/1 Intramuscular GlaxoSmithKline 2005-12-14 2005-12-14 US Ancef Inj Pws 10gm/vial USP Powder, for solution 10 g / vial Intravenous Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1974-12-31 2000-07-25 Canada 
Ancef Inj Pws 1gm/vial USP Powder, for solution 1 g / vial Intramuscular; Intravenous Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1974-12-31 2000-12-15 Canada Ancef Inj Pws 500mg/vial USP Powder, for solution 500 mg / vial Intramuscular; Intravenous Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1992-12-31 2000-01-07 Canada Cefazolin Injection 1 g/100mL Intramuscular West-ward Pharmaceutical Corp. 2008-11-18 2008-11-18 US Cefazolin Injection, powder, for solution 2 g/1 Intravenous WG Critical Care, LLC 2023-05-18 Not applicable US Cefazolin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Interchem Corporation 2008-11-07 2008-12-11 US Cefazolin Injection, powder, lyophilized, for solution 2 g/1 Intravenous Hikma Pharmaceuticals USA Inc. 2023-03-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefazolin Injection, powder, for solution 10 g/1 Intravenous Sagent Pharmaceuticals 2015-07-01 2024-03-31 US Cefazolin Powder, for solution 1 g/3mL Intramuscular; Intravenous Fresenius Kabi USA, LLC 2011-07-15 Not applicable US Cefazolin Injection, powder, for solution 10 g/1 Intravenous; Parenteral Sandoz 1988-12-09 2014-09-30 US Cefazolin Injection, powder, for solution 330 mg/1mL Intramuscular; Intravenous Hikma Pharmaceuticals USA Inc. 2001-09-18 Not applicable US Cefazolin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous; Parenteral Sandoz Inc 1988-12-09 2010-06-15 US Cefazolin Injection, powder, for solution 330 mg/1mL Intramuscular; Intravenous A-S Medication Solutions 2001-09-18 Not applicable US Cefazolin Injection, powder, for solution 225 mg/1mL Intramuscular; Intravenous Henry Schein Inc. 2022-01-09 Not applicable US Cefazolin Powder, for solution 1 g/3mL Intramuscular; Intravenous Cardinal Health 2011-07-15 2018-09-30 US Cefazolin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Apotex Corp. 2022-09-01 Not applicable US Cefazolin Injection, powder, for solution 500 mg/1 Intramuscular; Intravenous; Parenteral Sandoz Inc 1988-12-09 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CEFAMEZIN 1000 MG IM STERİL ENJEKTABL TOZ İÇEREN FLAKON, 1 ADET Cefazolin sodium (1000 mg) + Lidocaine hydrochloride (0.5 %) Injection, powder, for solution Intramuscular SANOFİ İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
CEFAMEZIN 250 MG IM ENJEKTABL TOZ İÇEREN FLAKON, 1 ADET Cefazolin sodium (250 mg) + Lidocaine hydrochloride (0.5 %) Injection, powder, for solution Intramuscular SANOFİ İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey CEFAMEZIN 500 MG IM ENJEKTABL TOZ İÇEREN FLAKON, 1 ADET Cefazolin sodium (500 mg) + Lidocaine hydrochloride (0.5 %) Injection, powder, for solution Intramuscular SANOFİ İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cefazolin Sodium Cefazolin sodium (30 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2013-12-05 Not applicable US Cefazolin Sodium Cefazolin sodium (100 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2013-11-14 Not applicable US Cefazolin Sodium Cefazolin sodium (2 g/100mL) Injection, solution Intravenous Cantrell Drug Company 2011-09-30 2015-01-14 US Cefazolin Sodium Cefazolin sodium (2 g/100mL) Injection, solution Intravenous Cantrell Drug Company 2011-11-01 Not applicable US
Categories
- ATC Codes
- J01DB04 — Cefazolin
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- First-Generation Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- Sulfur Compounds
- Thiazines
- 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
- External Links
- Human Metabolome Database
- HMDB0015422
- KEGG Drug
- D02299
- KEGG Compound
- C06880
- PubChem Compound
- 33255
- PubChem Substance
- 46506123
- ChemSpider
- 30723
- BindingDB
- 50370587
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Surgical Site Infections 1 4 Completed Basic Science Burns / Surgery / Wound Infections 1 4 Completed Basic Science Cesarean Delivery / Obesity / Wound Infections 1 4 Completed Other Post-gastrointestinal bypass surgery 1 4 Completed Prevention Aortic Valve Disorder / Congenital Heart Disease (CHD) 1 4 Completed Prevention Arrhythmia 2 4 Completed Prevention Carpal Tunnel Syndrome (CTS) 1 4 Completed Prevention Empyema / Pleural Effusions / Pleuritis 1 4 Completed Prevention Infection; Cesarean Section / Obesity / Obesity, Morbid / Pregnancy 1 4 Completed Prevention Inguinal Hernias 2
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
Form Route Strength Injection Intramuscular 1 g/1 Injection Intramuscular 10 g/1 Injection 1 G Injection 250 MG Injection 500 MG Injection, powder, for solution Intramuscular 250 MG Injection, powder, for solution Intramuscular 500 MG Injection, powder, for solution Intramuscular; Parenteral 1000 MG/4ML Injection, powder, for solution Intramuscular; Parenteral 250 MG/2ML Injection, powder, for solution Intramuscular; Parenteral 500 MG/2ML Injection, powder, for solution Intravenous; Parenteral 1000 MG/10ML Injection, powder, for solution Intramuscular Injection Intramuscular; Intravenous 1000 mg Injection Intramuscular; Intravenous 250 mg Injection Intramuscular; Intravenous 500 mg Injection Intramuscular 1 g/100mL Injection Intramuscular 500 mg/10mL Injection Intravenous 500 mg/50mL Injection, powder, for solution Intramuscular; Intravenous 1 g/3mL Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, for solution Intramuscular; Intravenous 225 mg/1mL Injection, powder, for solution Intramuscular; Intravenous 330 mg/1mL Injection, powder, for solution Intramuscular; Intravenous 500 mg/10mL Injection, powder, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, for solution Intramuscular; Intravenous 500 mg/2.2mL Injection, powder, for solution Intramuscular; Intravenous; Parenteral 1 g/1 Injection, powder, for solution Intramuscular; Intravenous; Parenteral 500 mg/1 Injection, powder, for solution Intravenous 1 g/1 Injection, powder, for solution Intravenous 1 g/5mL Injection, powder, for solution Intravenous 10 g/1 Injection, powder, for solution Intravenous 2 g/1 Injection, powder, for solution Intravenous 20 g/1 Injection, powder, for solution Intravenous 20 g/100mL Injection, powder, for solution Intravenous 3 g/1 Injection, powder, for solution Intravenous 500 mg/1 Injection, powder, for solution Intravenous; Parenteral 10 g/1 Injection, powder, lyophilized, for solution Intramuscular 1 g/1 Injection, powder, lyophilized, for solution Intravenous 100 g/1 Injection, powder, lyophilized, for solution Intravenous 2 g/1 Injection, powder, lyophilized, for solution Intravenous 300 g/1 Injection, solution Intravenous 1 g/50mL Powder, for solution Intramuscular; Intravenous 1 g/3mL Powder, for solution Intramuscular; Intravenous 500 mg/2.2mL Powder, for solution Intravenous 10 g/1 Powder, for solution Intravenous 20 g/100mL Powder, for solution Intramuscular; Intravenous 1 g / vial Powder, for solution Intramuscular; Intravenous 500 mg / vial Powder, for solution Intravenous 10 g / vial Powder, for solution Intramuscular; Intravenous 20 g / vial Injection, powder, for solution Intramuscular; Intravenous 1 g Powder, for solution Intramuscular; Intravenous 1.0 g / vial Powder, for solution Intravenous 100 g / bag Powder, for solution Intravenous 20 g / vial Solution Intravenous 20 mg / mL Injection, powder, for solution Intramuscular; Intravenous 1 g/vial Injection, powder, for solution Intravenous Injection, powder, for solution Parenteral Injection, solution Intramuscular; Intravenous Injection, powder, for solution Injection, powder, for solution 1 g Injection, solution Intravenous 100 mg/1mL Injection, solution Intravenous 2 g/100mL Injection, solution Intravenous 30 mg/1mL Solution Intravenous 1 g/50mL Solution Intravenous 2 g/50mL Powder, for solution Intramuscular; Intravenous 2 g / vial Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Intravenous Injection, powder, lyophilized, for solution Intramuscular; Intravenous 500 MG Injection, powder, for solution Intravenous Powder Intramuscular Injection, powder, for solution Intramuscular 1 g Injection, powder, for solution Intramuscular; Parenteral 1 G/4ML Injection, powder, for solution Intramuscular; Parenteral 500 MG/3ML Injection, powder, for solution Intravenous; Parenteral 1 G/10ML Injection, powder, lyophilized, for solution Parenteral 1 g Injection, powder, for solution Intravenous 250 MG Injection, powder, for solution Intravenous 500 MG Injection, powder, for solution Parenteral 1 G Injection, powder, for solution Parenteral 500 MG Injection, solution Intramuscular 1 g Injection Intramuscular 250 mg Injection Intramuscular 500 mg Injection Intramuscular; Intravenous 1 g Injection Intramuscular 1 g Injection, powder, for solution Intramuscular; Intravenous 1 gm Injection, powder, for solution Intramuscular; Intravenous 1 gr Injection, powder, for solution Intramuscular; Intravenous 250 mg Injection, powder, for solution Intramuscular; Intravenous 500 mg Powder, for solution Intravenous 1 g / vial Powder, for solution Intravenous 500 mg / vial Injection, powder, for solution Intramuscular 1000 mg Injection Intramuscular; Intravenous Injection Intramuscular 1000 mg Powder, for solution Intramuscular; Intravenous 10 g / vial Injection Injection, powder, for solution Intramuscular Powder, for solution Injection, powder, for solution Intramuscular; Intravenous 1000 mg Powder Intramuscular 250 mg/1vial Powder Intramuscular 500 mg/1vial - Prices
Unit description Cost Unit Cefazolin 10 g/vial 58.66USD vial Sterile Cefazolin Sodium 10 g/vial 58.66USD vial Cefazolin 20 gm bulk vial 29.69USD vial Cefazolin 10 gm vial 24.0USD vial Cefazolin 1 g/vial 6.29USD vial Sterile Cefazolin Sodium 1 g/vial 6.29USD vial Cefazolin 1 gm-d5w bag 5.04USD each Cefazolin 500 mg/vial 4.19USD vial Sterile Cefazolin Sodium 500 mg/vial 4.19USD vial Cefazolin 1 gm vial 3.12USD vial Cefazolin sod 100 gm bulk bag 1.26USD g Cefazolin sod-water 1 g/10 ml 0.93USD ml Cefazolin-d5w 2 g/100 ml 0.17USD ml Cefazolin-ns 2 g/100 ml 0.08USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -0.58 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.487 mg/mL ALOGPS logP -0.4 ALOGPS logP -1.5 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 2.84 Chemaxon pKa (Strongest Basic) 0.26 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 156.09 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 119.86 m3·mol-1 Chemaxon Polarizability 41.57 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5119 Blood Brain Barrier - 0.987 Caco-2 permeable - 0.7891 P-glycoprotein substrate Substrate 0.7863 P-glycoprotein inhibitor I Non-inhibitor 0.8663 P-glycoprotein inhibitor II Non-inhibitor 0.9603 Renal organic cation transporter Non-inhibitor 0.8574 CYP450 2C9 substrate Non-substrate 0.7588 CYP450 2D6 substrate Non-substrate 0.818 CYP450 3A4 substrate Non-substrate 0.5161 CYP450 1A2 substrate Non-inhibitor 0.8949 CYP450 2C9 inhibitor Non-inhibitor 0.8746 CYP450 2D6 inhibitor Non-inhibitor 0.9178 CYP450 2C19 inhibitor Non-inhibitor 0.8363 CYP450 3A4 inhibitor Non-inhibitor 0.9377 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6362 Ames test Non AMES toxic 0.6675 Carcinogenicity Non-carcinogens 0.8876 Biodegradation Not ready biodegradable 0.7464 Rat acute toxicity 2.2215 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8898 hERG inhibition (predictor II) Non-inhibitor 0.8711
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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
- 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
- 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
- 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]
- 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
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
- 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]
- 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
- 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
- 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 ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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 September 29, 2023 09:04