Identification
- Summary
Cefotaxime is a third generation cephalosporin used to treat susceptible Gram negative and Gram positive bacterial infections.
- Brand Names
- Claforan
- Generic Name
- Cefotaxime
- DrugBank Accession Number
- DB00493
- Background
Cefotaxime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime sodium is marketed under various trade names including Claforan (Sanofi-Aventis).
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cefotaxime (DB00493)
- Weight
- Average: 455.465
Monoisotopic: 455.056939303 - Chemical Formula
- C16H17N5O7S2
- Synonyms
- (6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-3-(acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefotaxim
- Cefotaxima
- Céfotaxime
- Cefotaxime
- Cefotaximum
- Cephotaxime
- External IDs
- CTX
- HR 756
- RU 24662
- RU 24756
Pharmacology
- Indication
Used to treat gonorrhoea, meningitis, and severe infections including infections of the kidney (pyelonephritis) and urinary system. Also used before an operation to prevent infection after surgery.
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
- Bone and Joint Infections caused by susceptible Bacterial Infections
- Central Nervous System Infections caused by susceptible Bacterial Infections
- Genitourinary tract infection caused by susceptible Bacterial Infections
- Gynaecological infection caused by susceptible bacteria
- Intraabdominal Infections caused by susceptible Bacterial Infections
- Lower Respiratory Tract Infection (LRTI) caused by susceptible bacteria
- Postoperative Wound Infection
- Septicemia caused by susceptible Bacterial Infections
- Skin and skin-structure infections caused by susceptible bacteria
- 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
Cefotaxime is a third generation intravenous cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotaxime works by inhibiting bacterial cell wall biosynthesis. A positive feature of cefotaxime is that it display a resistance to penicillinases and is useful to treat infections that are resistant to penicillin derivatives.
- Mechanism of action
The bactericidal activity of cefotaxime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefotaxime shows high affinity for penicillin-binding proteins in the cell wall including PBP Ib and PBP III.
Target Actions Organism APenicillin-binding protein 1b inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2a inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 3 inhibitorBacillus subtilis (strain 168) APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) USolute carrier family 22 member 6 Not Available Humans USolute carrier family 22 member 8 Not Available Humans USolute carrier family 22 member 11 Not Available Humans USolute carrier family 22 member 7 Not Available Humans USolute carrier family 15 member 1 Not Available Humans USerum albumin Not Available Humans UBeta-lactamase Not Available Acinetobacter baumannii USolute carrier family 15 member 2 Not Available Humans - Absorption
Rapidly absorbed following intramuscular injection.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite. The desacetyl metabolite has been shown to contribute to the bactericidal activity. Two other urinary metabolites (M2 and M3) account for about 20-25%. They lack bactericidal activity.
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- Route of elimination
Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite.
- Half-life
Approximately 1 hour.
- 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
Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions. Oral rat LD50 is over 20,000 mg/kg while intravenous rat LD50 is over 7,000 mg/kg.
- 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 Cefotaxime 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 Cefotaxime. Acamprosate The excretion of Acamprosate can be decreased when combined with Cefotaxime. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefotaxime is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefotaxime is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefotaxime is combined with Acenocoumarol. Acetaminophen Cefotaxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Cefotaxime. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Cefotaxime is combined with Acetylsalicylic acid. Aclidinium Cefotaxime may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- 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 Cefotaxime sodium 258J72S7TZ 64485-93-4 AZZMGZXNTDTSME-REMKHYEUSA-M - International/Other Brands
- Rantaksym (Ranbaxy) / Raxim (Ranbaxy) / Spinocef (Abbott) / Sporim (Pharmacare) / Talcef (Ipca)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefotaxime Powder, for solution 2 g/1 Intramuscular; Intravenous SteriMax Inc. 2019-08-01 Not applicable US 
Cefotaxime Powder, for solution 1 g/1 Intramuscular; Intravenous SteriMax Inc. 2019-08-01 Not applicable US Cefotaxime and Dextrose Injection 1 g/50mL Intravenous B. Braun Medical Inc. 2004-08-10 2005-08-01 US Cefotaxime and Dextrose Injection 2 g/50mL Intravenous B. Braun Medical Inc. 2004-08-10 2005-08-01 US Cefotaxime Sodium for Injection BP Powder, for solution 1 g / vial Intramuscular; Intravenous Aurobindo Pharma Limited (Unit Vi) Not applicable Not applicable Canada 
Cefotaxime Sodium for Injection BP Powder, for solution 0.5 g / vial Intramuscular; Intravenous Aurobindo Pharma Limited (Unit Vi) Not applicable Not applicable Canada Cefotaxime Sodium for Injection BP Powder, for solution 2 g / vial Intramuscular; Intravenous Aurobindo Pharma Limited (Unit Vi) Not applicable Not applicable Canada Cefotaxime Sodium for Injection, BP Powder, for solution 500 mg / vial Intramuscular; Intravenous Hospira Healthcare Ulc 2010-07-07 2018-03-21 Canada Cefotaxime Sodium for Injection, BP Powder, for solution 2.0 g / vial Intramuscular; Intravenous Hospira Healthcare Ulc 2010-07-06 2018-03-21 Canada Cefotaxime Sodium for Injection, BP Powder, for solution 250 mg / vial Intramuscular; Intravenous Hospira Healthcare Ulc Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefotaxime Injection, powder, for solution 2 g/1 Intramuscular; Intravenous Wockhardt USA LLC. 2008-06-20 Not applicable US Cefotaxime Injection, powder, for solution 10 g/1 Intravenous Pfizer Laboratories, Division of Pfizer Inc 2009-11-05 2012-01-31 US Cefotaxime Injection, powder, for solution 1 g/1 Intravenous Hospira, Inc. 2016-02-19 2016-02-20 US Cefotaxime Injection 10 g/1 Intravenous West-Ward Pharmaceuticals Corp 2002-11-20 Not applicable US Cefotaxime Injection, powder, for solution 500 mg/1 Intramuscular; Intravenous Pfizer Laboratories, Division of Pfizer Inc 2009-11-05 2012-12-11 US Cefotaxime Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Aurobindo Pharma 2009-11-05 2012-01-31 US Cefotaxime Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Hikma Pharmaceuticals USA Inc. 2002-11-20 Not applicable US Cefotaxime Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Lupin Pharmaceuticals, Inc. 2005-05-27 2018-01-25 US Cefotaxime Injection, powder, for solution 500 mg/1mL Intramuscular; Intravenous Wockhardt 2008-06-20 Not applicable US Cefotaxime Injection, powder, for solution 2 g/1 Intramuscular; Intravenous Pfizer Laboratories, Division of Pfizer Inc 2009-11-05 2012-12-11 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image SEFOTAK 1 G IM ENJEKSİYONLUK TOZ İÇEREN FLAKON, 1 ADET Cefotaxime sodium (1 g) + Lidocaine hydrochloride (1 %) Injection 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 Cefotaxime Cefotaxime sodium (1 g/1) Powder, for solution Intramuscular; Intravenous SteriMax Inc. 2019-08-01 Not applicable US Cefotaxime Cefotaxime sodium (2 g/1) Powder, for solution Intramuscular; Intravenous SteriMax Inc. 2019-08-01 Not applicable US
Categories
- ATC Codes
- J01DD01 — Cefotaxime
- Drug Categories
- Agents that reduce seizure threshold
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephacetrile
- Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Sulfur Compounds
- Thiazines
- Third-Generation Cephalosporins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporin 3'-esters
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines show 10 more
- Substituents
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Azole show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, 1,3-thiazole, oxime O-ether (CHEBI:204928)
- Affected organisms
- Pseudomonas aeruginosa
- Streptococcus pyogenes
- Streptococcus pneumoniae
- Haemophilus influenzae
- Neisseria gonorrhoeae
- Escherichia coli
- Staphylococcus aureus
- Staphylococcus epidermidis
- Serratia marcescens
- Proteus vulgaris
- Proteus mirabilis
- Providencia stuartii
- Providencia rettgeri
- Morganella morganii
- Haemophilus parainfluenzae
- Acinetobacter spp.
- Enterobacter spp.
- Klebsiella spp.
- Citrobacter spp.
- Clostridium spp.
- Peptococcus spp.
- Peptostreptococcus spp.
- Bacteroides spp.
- Fusobacterium spp.
- Enterococcus
Chemical Identifiers
- UNII
- N2GI8B1GK7
- CAS number
- 63527-52-6
- InChI Key
- GPRBEKHLDVQUJE-QSWIMTSFSA-N
- InChI
- InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
- IUPAC Name
- (6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
References
- Synthesis Reference
Ingolf Macher, Gerhard Widschwenter, "Production of cefotaxime and new sodium salts." U.S. Patent US5831086, issued May, 1992.
US5831086- General References
- FDA Approved Drug Products: Claforan (cefotaxime) for injection [Link]
- External Links
- Human Metabolome Database
- HMDB0014636
- KEGG Drug
- D07647
- KEGG Compound
- C06885
- PubChem Compound
- 5742673
- PubChem Substance
- 46506911
- ChemSpider
- 4674877
- BindingDB
- 50482777
- 2186
- ChEBI
- 204928
- ChEMBL
- CHEMBL1730
- ZINC
- ZINC000004468780
- Therapeutic Targets Database
- DAP000146
- PharmGKB
- PA448852
- PDBe Ligand
- CE3
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cefotaxime
- PDB Entries
- 3hlw / 4kot / 4pm5 / 4pm7 / 4pm9 / 5nzy / 6c79
- FDA label
- Download (241 KB)
- MSDS
- Download (38.9 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Critically Ill Patients 1 4 Completed Treatment Cirrhosis of the Liver / SBP 1 4 Completed Treatment Diabetes Mellitus 1 4 Completed Treatment Urinary Tract Infection 1 4 Completed Treatment Ventilator Associated Bacterial Pneumonia (VABP) 1 4 Not Yet Recruiting Treatment Spontaneous Bacterial Peritonitis (SBP) 1 4 Unknown Status Treatment Cirrhosis of the Liver 1 4 Unknown Status Treatment Infectious Disease - Resistant Enterobacteriaceae (Diagnosis) 1 3 Completed Prevention Critically Ill Patients / Sepsis / Septic Shock / Ventilator Associated Bacterial Pneumonia (VABP) 1 3 Completed Treatment Emergence of Bacterial Resistance to Antibiotics 1
Pharmacoeconomics
- Manufacturers
- App pharmaceuticals llc
- Hikma farmaceutica lda
- Wockhardt ltd
- B braun medical inc
- Aurobindo pharma ltd
- Cephazone pharma llc
- Lupin ltd
- Orchid healthcare
- Sanofi aventis us llc
- Packagers
- APP Pharmaceuticals
- Aurobindo Pharma Ltd.
- Baxter International Inc.
- Cardinal Health
- Hikma Pharmaceuticals
- Hospira Inc.
- Lupin Pharmaceuticals Inc.
- Patheon Inc.
- Pfizer Inc.
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- West-Ward Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Solution Intravenous Injection, powder, for solution Intramuscular; Parenteral 1 G/4ML Injection, powder, for solution Intravenous; Parenteral 2 G/10ML Injection, powder, for solution Parenteral 1 G/4ML Injection Intramuscular; Intravenous 500 mg Injection, powder, for solution Parenteral Injection, powder, for solution Parenteral 1 g Injection, powder, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Parenteral 500 MG/2ML Powder, for solution Intravenous Injection, powder, for solution Intramuscular 1 G/4ML Injection, powder, for solution Intravenous 2 G/10ML Injection, powder, for solution Intravenous; Parenteral 1 G/4ML Injection, powder, for solution Intravenous; Parenteral 500 MG/2ML Powder, for solution Intravenous 2 G Injection Intravenous 10 g/1 Injection, powder, for solution Intramuscular; Intravenous 1 g/1mL Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/1mL Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, for solution Intramuscular; Intravenous 500 mg/1mL Injection, powder, for solution Intravenous 1 g/1 Injection, powder, for solution Intravenous 10 g/1 Injection, powder, for solution Intravenous 2 g/1 Powder, for solution Intramuscular; Intravenous 1 g/1 Powder, for solution Intramuscular; Intravenous 2 g/1 Injection Intravenous 1 g/50mL Injection Intravenous 2 g/50mL Powder, for solution Intravenous 2 g/100ml Injection, powder, for solution Intramuscular; Parenteral 1 G Injection, powder, for solution Intravenous; Parenteral 1 G Injection, powder, for solution Intravenous; Parenteral 2 G Injection, powder, for solution Intravenous; Parenteral 250 MG Injection, powder, for solution Intravenous; Parenteral 500 MG Injection, powder, for solution Intramuscular; Parenteral 1000 MG/4ML Injection, powder, for solution Intravenous; Parenteral 2000 MG/10ML Injection, powder, for solution Parenteral 1000 MG/4ML Powder, for solution Intramuscular; Intravenous 0.5 g / vial Powder, for solution Intramuscular; Intravenous 1 g / vial Powder, for solution Intramuscular; Intravenous 1.0 g / vial Powder, for solution Intramuscular; Intravenous 2 g / vial Powder, for solution Intramuscular; Intravenous 2.0 g / vial Powder, for solution Intramuscular; Intravenous 250 mg / vial Powder Not applicable 10 kg/10kg Powder, for solution Intramuscular Injection Intramuscular; Intravenous 1 g/50mL Injection Intramuscular; Intravenous 1 g/1 Injection Intramuscular; Intravenous 10 g/1 Injection Intramuscular; Intravenous 2 g/50mL Injection Intramuscular; Intravenous 2 g/1 Injection Intramuscular; Intravenous 500 mg/1 Injection, powder, for solution Intramuscular Injection, powder, for solution Intravenous Powder, for solution Powder, for solution Intramuscular; Intravenous 500 mg / vial Injection, powder, for solution Intramuscular; Intravenous 0.5 g Injection Intramuscular; Intravenous Injection, powder, lyophilized, for solution Intramuscular; Intravenous Powder, for solution Intravenous 1 g / vial Injection, powder, for solution 0.5 g Injection, solution Intramuscular; Intravenous Injection Intravenous Injection, solution Intramuscular; Intravenous 0.5 gr Injection, solution Intramuscular; Intravenous 1 g Injection, solution Intramuscular; Intravenous 2 g Solution 1.000 g Solution Intramuscular 500.000 mg Injection, powder, for solution Intravenous 1 g Injection, powder, for solution 1 g Injection Injection Intramuscular; Intravenous 1 gr Injection, powder, for solution Injection Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Intravenous 1000 mg Injection, powder, for solution Intramuscular; Intravenous 500 MG Injection Intramuscular; Intravenous 0.5 g Injection 2 g Injection, powder, for solution Intramuscular; Intravenous 500 mg/2ml Injection Intramuscular 500 mg Injection Intramuscular Injection, powder, for solution Intramuscular; Intravenous 1 g/4ml Injection, powder, for solution Parenteral 2 G Solution Intramuscular 1.048 g Injection Intramuscular; Intravenous 1000 mg Injection Intravenous 2 g Solution Parenteral 500.000 g Injection Parenteral Solution Parenteral 1.000 g Injection, powder, for solution Parenteral 250 MG/2ML Injection, powder, for solution Parenteral 500 MG/2ML Powder, for solution 1 G Powder, for solution 2 G Powder 500 mg/1vial - Prices
Unit description Cost Unit Cefotaxime sodium 10 gm vial 31.43USD vial Claforan 10 gm vial 28.64USD vial Claforan 2 g/vial 20.72USD vial Claforan 2 gm infusion btl 11.76USD each Claforan 1 g/vial 10.36USD vial Claforan 500 mg/vial 6.76USD vial Cefotaxime sodium 2 gm vial 6.48USD vial Claforan 1 gm infusion btl 6.08USD each Claforan 2 gm vial 5.74USD vial Cefotaxime sodium 1 gm vial 3.24USD vial Claforan 1 gm vial 2.12USD vial 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 water solubility Soluble Not Available logP -0.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.146 mg/mL ALOGPS logP 0.14 ALOGPS logP -1.5 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 2.73 Chemaxon pKa (Strongest Basic) 3.58 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 173.51 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 105.11 m3·mol-1 Chemaxon Polarizability 41.77 Å3 Chemaxon Number of Rings 3 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 - 0.6285 Blood Brain Barrier - 0.9877 Caco-2 permeable - 0.761 P-glycoprotein substrate Substrate 0.7271 P-glycoprotein inhibitor I Non-inhibitor 0.9091 P-glycoprotein inhibitor II Inhibitor 0.5397 Renal organic cation transporter Non-inhibitor 0.8465 CYP450 2C9 substrate Non-substrate 0.8527 CYP450 2D6 substrate Non-substrate 0.8222 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.8014 CYP450 2C9 inhibitor Non-inhibitor 0.812 CYP450 2D6 inhibitor Non-inhibitor 0.8945 CYP450 2C19 inhibitor Non-inhibitor 0.7749 CYP450 3A4 inhibitor Non-inhibitor 0.7505 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9174 Ames test Non AMES toxic 0.8513 Carcinogenicity Non-carcinogens 0.8653 Biodegradation Not ready biodegradable 0.9931 Rat acute toxicity 1.7964 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9873 hERG inhibition (predictor II) Non-inhibitor 0.8723
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Not Available
- Gene Name
- pbp1b
- Uniprot ID
- Q7CRA4
- Uniprot Name
- Penicillin-binding protein 1b
- Molecular Weight
- 89479.92 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Not Available
- Gene Name
- pbp2a
- Uniprot ID
- Q8DNB6
- Uniprot Name
- Penicillin-binding protein 2a
- Molecular Weight
- 80797.94 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Bacillus subtilis (strain 168)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Not Available
- Gene Name
- pbpC
- Uniprot ID
- P42971
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 74405.915 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Selakovitch-Chenu L, Seroude L, Sicard AM: The role of penicillin-binding protein 3 (PBP 3) in cefotaxime resistance in Streptococcus pneumoniae. Mol Gen Genet. 1993 May;239(1-2):77-80. [Article]
- Krauss J, Hakenbeck R: A mutation in the D,D-carboxypeptidase penicillin-binding protein 3 of Streptococcus pneumoniae contributes to cefotaxime resistance of the laboratory mutant C604. Antimicrob Agents Chemother. 1997 May;41(5):936-42. [Article]
- Georgopapadakou NH, Smith SA, Cimarusti CM, Sykes RB: Binding of monobactams to penicillin-binding proteins of Escherichia coli and Staphylococcus aureus: relation to antibacterial activity. Antimicrob Agents Chemother. 1983 Jan;23(1):98-104. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Cell wall formation.
- Gene Name
- pbpA
- Uniprot ID
- Q8DR59
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M6
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- 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
- Baneres-Roquet F, Gualtieri M, Villain-Guillot P, Pugniere M, Leonetti JP: Use of a surface plasmon resonance method to investigate antibiotic and plasma protein interactions. Antimicrob Agents Chemother. 2009 Apr;53(4):1528-31. doi: 10.1128/AAC.00971-08. Epub 2009 Jan 21. [Article]
- Kind
- Protein
- Organism
- Acinetobacter baumannii
- Pharmacological action
- Unknown
- General Function
- Beta-lactamase activity
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- B2ZTR6
- Uniprot Name
- Beta-lactamase
- Molecular Weight
- 40542.17 Da
References
- Rodriguez-Martinez JM, Nordmann P, Ronco E, Poirel L: Extended-spectrum cephalosporinase in Acinetobacter baumannii. Antimicrob Agents Chemother. 2010 Aug;54(8):3484-8. doi: 10.1128/AAC.00050-10. Epub 2010 Jun 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Pedretti A, De Luca L, Marconi C, Regazzoni L, Aldini G, Vistoli G: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorg Med Chem. 2011 Aug 1;19(15):4544-51. doi: 10.1016/j.bmc.2011.06.027. Epub 2011 Jun 16. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- 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
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2023 01:14