Cefuroxime

Identification

Summary

Cefuroxime is a cephalosporin indicated for the treatment of a variety of infections including acute bacterial otitis media, several upper respiratory tract infections, skin infections, urinary tract infections, gonorrhea, early Lyme disease, and impetigo.

Brand Names
Ceftin
Generic Name
Cefuroxime
DrugBank Accession Number
DB01112
Background

Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 424.385
Monoisotopic: 424.068884198
Chemical Formula
C16H16N4O8S
Synonyms
  • (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefuroxim
  • Cefuroxima
  • Cefuroxime
  • Cefuroximo
  • Cefuroximum
  • Cephuroxime

Pharmacology

Indication

For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute bacterial exacerbation of chronic bronchitis••••••••••••••••••
Used in combination to treatAnimal bite••• •••••
Prophylaxis ofBacterial infection••••••••••••
Treatment ofBacterial infections••••••••••••
Treatment ofBone and joint infections••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug

Mechanism of action

Cefuroxime, like the penicillins, is a beta-lactam antibiotic. 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; it is possible that cefuroxime interferes with an autolysin inhibitor.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Clostridium perfringens (strain 13 / Type A)
Absorption

Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).

Volume of distribution

Not Available

Protein binding

50% to serum protein

Metabolism

The axetil moiety is metabolized to acetaldehyde and acetic acid.

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Approximately 80 minutes following intramuscular or intravenous injection.

Clearance

Not Available

Adverse Effects
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Toxicity

Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.

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
AbacavirCefuroxime 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 Cefuroxime.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cefuroxime is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefuroxime is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefuroxime is combined with Acenocoumarol.
Food Interactions
  • Take with food. Food increases absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cefuroxime axetilZ49QDT0J8Z64544-07-6KEJCWVGMRLCZQQ-YJBYXUATSA-N
Cefuroxime sodiumR8A7M9MY6156238-63-2URDOHUPGIOGTKV-JTBFTWTJSA-M
Product Images
International/Other Brands
Cefurax (Lindopharm) / Elobact (GlaxoSmithKline) / Oraxim (Malesci) / Sharox (Fahrenheit) / Supacef (GlaxoSmithKline) / Zinacef danmark / Zinnat (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CeftinPowder, for suspension125 mg/5mLOralGlaxoSmithKline LLC2004-06-022018-09-30US flag
CeftinTablet, film coated250 mg/1OralPhysicians Total Care, Inc.1989-10-012012-06-30US flag
CeftinPowder, for suspension250 mg/5mLOralGlaxoSmithKline LLC2004-06-022018-09-30US flag
CeftinTablet, film coated500 mg/1OralGlaxoSmithKline2006-09-01Not applicableUS flag
CeftinTablet, film coated250 mg/1OralGlaxoSmithKline LLC1989-10-012018-04-30US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-cefuroximeTablet500 mgOralApotex Corporation2001-08-29Not applicableCanada flag
Apo-cefuroximeTablet250 mgOralApotex Corporation2001-08-29Not applicableCanada flag
Auro-cefuroximeTablet500 mgOralAuro Pharma Inc2012-01-13Not applicableCanada flag
Auro-cefuroximeTablet250 mgOralAuro Pharma Inc2012-01-13Not applicableCanada flag
CefuroximeInjection, powder, for solution750 mg/100mLIntravenousWG Critical Care, LLC2012-10-04Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BIGCEF 250/125 MG FILM KAPLI TABLET, 10 ADETCefuroxime axetil (250 mg) + Clavulanic acid (125 mg)Tablet, coatedNEUTEC İLAÇ SAN. TİC. A.Ş.2012-12-26Not applicableTurkey flag
BIGCEF 250/125 MG FILM KAPLI TABLET, 14 ADETCefuroxime axetil (250 mg) + Clavulanic acid (125 mg)Tablet, coatedNEUTEC İLAÇ SAN. TİC. A.Ş.2012-12-26Not applicableTurkey flag
BIGCEF 250/125 MG FILM KAPLI TABLET, 20 ADETCefuroxime axetil (250 mg) + Clavulanic acid (125 mg)Tablet, coatedNEUTEC İLAÇ SAN. TİC. A.Ş.2012-12-26Not applicableTurkey flag
BIGCEF 500/125 MG FILM KAPLI TABLET, 10 ADETCefuroxime axetil (500 mg) + Clavulanic acid (125 mg)Tablet, coatedNEUTEC İLAÇ SAN. TİC. A.Ş.2012-12-26Not applicableTurkey flag
BIGCEF 500/125 MG FILM KAPLI TABLET, 14 ADETCefuroxime axetil (500 mg) + Clavulanic acid (125 mg)Tablet, coatedNEUTEC İLAÇ SAN. TİC. A.Ş.2012-12-26Not applicableTurkey flag

Categories

ATC Codes
S01AA27 — CefuroximeJ01DC02 — CefuroximeJ01RA03 — Cefuroxime and metronidazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporin 3'-carbamates
Alternative Parents
N-acyl-alpha amino acids and derivatives / 1,3-thiazines / Tertiary carboxylic acid amides / Carbamate esters / Furans / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Organic carbonic acids and derivatives / Thiohemiaminal derivatives
show 10 more
Substituents
Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxime O-ether, furans, 3-(carbamoyloxymethyl)cephalosporin (CHEBI:3515)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
O1R9FJ93ED
CAS number
55268-75-2
InChI Key
JFPVXVDWJQMJEE-IZRZKJBUSA-N
InChI
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
IUPAC Name
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O

References

Synthesis Reference

Vijay Kumar Handa, Ramesh Dandala, Jag Mohan Khanna, "Process for the preparation of cefuroxime." U.S. Patent US6235896, issued February, 1976.

US6235896
General References
  1. Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. [Article]
Human Metabolome Database
HMDB0015244
KEGG Drug
D00262
KEGG Compound
C06894
PubChem Compound
5479529
PubChem Substance
46506681
ChemSpider
4586393
BindingDB
50422689
RxNav
2194
ChEBI
3515
ChEMBL
CHEMBL1436
ZINC
ZINC000003871978
Therapeutic Targets Database
DAP000445
PharmGKB
PA448868
PDBe Ligand
KOV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cefuroxime
PDB Entries
4kov
FDA label
Download (809 KB)
MSDS
Download (52.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchAntibiotic Resistant Infection / Uncomplicated Urinary Tract Infections1
4CompletedPreventionInfection1
4CompletedPreventionInfection Prophylaxis in Colo Rectal Surgery1
4CompletedPreventionObesity; Drug1
4CompletedPreventionPostoperative Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • B. Braun Melsungen AG
  • Baxter International Inc.
  • BMH Ltd.
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Cura Pharmaceutical Co. Inc.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Dorx LLC
  • Elan Pharmaceuticals Inc.
  • Eli Lilly & Co.
  • F Hoffmann-La Roche Ltd.
  • Forum Products Inc.
  • GC Hanford Manufacturing Co.
  • GlaxoSmithKline Inc.
  • Greenstone LLC
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Liberty Pharmaceuticals
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Orchid Healthcare
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Sagent Pharmaceuticals
  • Samson Medical Technologies
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • World Gen LLC
  • Zyber Pharmaceuticals
Dosage Forms
FormRouteStrength
InjectionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular750 mg
Injection, powder, for solution
Tablet, film coatedOral
Injection, powder, for solutionIntraocular50 MG
Injection, powder, for solutionParenteral50 mg
InjectionIntraocular50 mg
SuspensionOral
CapsuleOral
Tablet, coated
InjectionIntramuscular
TabletOral500.000 mg
SuspensionOral2.500 g
TabletOral250.000 mg
Injection, solutionIntramuscular250 mg
InjectionIntramuscular500 mg
InjectionIntramuscular750 mg
Injection, powder, for solutionIntravenous1.5 gr
InjectionIntramuscular; Intravenous0.75 G
Granule, for suspensionOral125 mg / 5 mL
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
PowderOral250 mg / pck
Powder, for solutionOral250 mg / pck
Powder, for solutionOral125 mg / 5 mL
TabletOral250 mg / tab
TabletOral500 mg / tab
InjectionIntravenous
Injection, solutionIntramuscular750 mg
Injection, solutionIntramuscular; Intravenous
GranuleOral125 MG/5ML
Injection, powder, for suspensionIntramuscular
InjectionIntramuscular; Intravenous1.5 gr
InjectionIntramuscular250 mg
Injection, powder, for solutionParenteral250 mg
Injection, powder, for solutionParenteral
Injection, powder, for solutionParenteral1500 mg
Injection, powder, for solutionParenteral750 mg
Injection, powder, for solution1500 mg
SolutionParenteral
Injection, powder, for suspensionIntramuscular1 G/4ML
Injection, powder, for suspensionIntramuscular500 MG/2ML
TabletOral
Injection, powder, for solution50 MG
Injection, powder, for solutionIntramuscular; Intravenous; Parenteral1.5 G
Injection, powder, for solutionIntramuscular; Intravenous; Parenteral750 MG
Injection, powder, for suspensionIntramuscular750 MG/3ML
Tablet, coatedOral125 MG
Injection, powder, for solutionIntramuscular; Intravenous750 mg/1
Injection, powder, for solutionIntravenous1.5 g/1
Injection, powder, for solutionIntravenous1.5 g/100mL
Injection, powder, for solutionIntravenous1.5 g/16mL
Injection, powder, for solutionIntravenous7.5 g/1
Injection, powder, for solutionIntravenous7.5 g/80mL
Injection, powder, for solutionIntravenous7.5 g/82.5mL
Injection, powder, for solutionIntravenous750 mg/8mL
Injection, powder, for solutionIntravenous750 mg/100mL
Injection, powder, for solutionIntravenous95 mg/1mL
Injection750 mg
Tablet, coatedOral250 mg
Tablet, coatedOral500 mg
TabletOral125 mg/1
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral125 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
SuspensionOral125 mg/5mL
SuspensionOral250 mg/1mL
Powder, for solutionIntravenous750 mg / vial
Injection, powder, for solutionIntravenous225 g/1
Injection, powder, for solutionIntravenous75 g/1
Injection, powder, for solutionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous1 g
Injection, powder, for solutionParenteral1 G
Injection, powder, for suspensionIntramuscular250 MG/ML
Powder, for solution1.5 G
Powder, for solution2 G
Powder, for solution750 MG
Injection, powder, for solutionIntramuscular; Intravenous1.5 g
Injection, powder, for solutionIntramuscular; Intravenous750 mg
GranuleOral125 MG
Injection, powder, lyophilized, for solutionIntravenous
SolutionParenteral1500 mg
SolutionParenteral750.000 mg
InjectionIntramuscular; Intravenous
Tablet, film coatedOral500 mg
Injection, powder, for solutionIntramuscular1 g
Injection, powder, for solutionIntramuscular250 mg
Injection, powder, for solutionIntramuscular500 mg
Powder, for solutionIntravenous1.5 g / vial
Powder, for solution
Injection, powder, for solution1 G
Powder, for solution1500 MG
Injection, powder, for solutionIntramuscular; Intravenous
SolutionParenteral750.00 mg
SuspensionOral1.250 g
TabletOral125 mg
Granule, for suspensionOral250 MG
InjectionIntramuscular; Intravenous1.5 G
Injection, solutionIntravenous1.5 mg
Injection, solutionIntravenous250 mg
TabletOral500 MG
Injection, powder, for solutionParenteral1.5 g
Injection, powder, for solutionIntramuscular
Injection, powder, for solutionIntravenous
InjectionIntramuscular
Injection, powder, for solutionIntraocular
Injection, powder, for solutionOphthalmic50 MG
SolutionIntravenous750.000 mg
Powder, for suspensionOral
InjectionIntramuscular; Intravenous1500 MG
InjectionIntramuscular; Intravenous750 MG
Injection, powder, for solutionIntramuscular; Intravenous750 mg/8.3mL
Injection, powder, for solutionIntramuscular; Intravenous90 mg/1mL
Injection, powder, for solutionIntravenous7.5 g/77mL
Injection, powder, for solutionIntravenous750 mg/8.3mL
Injection, powder, for solutionIntravenous90 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous1.5 g/1
Injection, powder, lyophilized, for solutionIntravenous750 mg/1
Injection, solutionIntravenous1.5 g/50mL
Injection, solutionIntravenous750 mg/50mL
Powder, for solutionIntramuscular; Intravenous1.5 g / vial
Powder, for solutionIntramuscular; Intravenous750 mg / vial
Powder, for solutionIntravenous7.5 g / vial
TabletOral250 mg
Injection, solutionIntramuscular; Intravenous750 mg
Granule, for suspensionOral125 mg/5ml
Granule, for suspensionOral250 mg/5mL
GranuleOral5 g
PowderOral250 mg/1vial
Tablet, film coatedOral250 mg
CapsuleOral500 mg
PowderOral750 mg/1vial
Tablet, film coatedOral125 mg
CapsuleOral250 mg
Prices
Unit descriptionCostUnit
Rocephin 10 gm vial478.32USD vial
Ceftin 20 500 mg tablet Bottle436.36USD bottle
Cefuroxime Axetil 250 mg/5ml Suspension 100ml Bottle121.27USD bottle
Rocephin 2 gm vial97.5USD vial
Cefzil 250 mg/5ml Suspension 100ml Bottle87.62USD bottle
Zinacef 7.5 gm vial65.94USD vial
Rocephin 1 gm Solution Vial65.53USD vial
Rocephin 1 gm vial62.02USD vial
Duricef 500 mg/5ml Suspension 100ml Bottle59.36USD bottle
Cefzil 125 mg/5ml Suspension 100ml Bottle48.36USD bottle
Duricef 500 mg/5ml Suspension 75ml Bottle46.93USD bottle
Maxipime 2 gram vial43.04USD vial
Velosef 250 mg/5ml Suspension 100ml Bottle23.99USD bottle
Maxipime 1 gm piggyback vial23.24USD vial
Duricef 250 mg/5ml Suspension 50ml Bottle22.99USD bottle
Maxipime 1 gram vial21.7USD vial
Ceftin 500 mg tablet20.98USD tablet
Cefuroxime 1.5 g/50 ml bag16.8USD each
Cedax 400 mg capsule16.13USD each
Zinacef 1.5 gm add-vant vial13.94USD vial
Zinacef 1.5 gm vial13.45USD vial
Cefuroxime sod 1.5 gm vial13.44USD vial
Ceftin 250 mg tablet11.74USD tablet
Cefzil 500 mg tablet9.77USD tablet
Cefuroxime axetil 500 mg tablet8.11USD tablet
Duricef 1 gm tablet7.35USD tablet
Cefzil 250 mg tablet4.76USD tablet
Ceftin 500 mg Tablet3.61USD tablet
Cefuroxime axetil 250 mg tablet2.82USD tablet
Velosef 500 mg capsule2.02USD capsule
Apo-Cefuroxime 500 mg Tablet2.02USD tablet
Ratio-Cefuroxime 500 mg Tablet2.02USD tablet
Ceftin 250 mg Tablet1.82USD tablet
Velosef 250 mg capsule1.03USD capsule
Apo-Cefuroxime 250 mg Tablet1.02USD tablet
Ratio-Cefuroxime 250 mg Tablet1.02USD tablet
Zinacef-water 1.5 gm/50 ml0.32USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2408198No2004-03-092022-11-21Canada flag
CA1328405No1994-04-122011-04-12Canada flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)218-225 °CNot Available
water solubilityFreely soluble as sodium salt (145 mg/L)Not Available
logP-0.16SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.284 mg/mLALOGPS
logP-0.24ALOGPS
logP-0.9Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.96Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area173.76 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity97.17 m3·mol-1Chemaxon
Polarizability38.87 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6504
Blood Brain Barrier-0.9863
Caco-2 permeable-0.7051
P-glycoprotein substrateSubstrate0.7253
P-glycoprotein inhibitor INon-inhibitor0.8621
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8688
CYP450 2C9 substrateNon-substrate0.8686
CYP450 2D6 substrateNon-substrate0.8196
CYP450 3A4 substrateSubstrate0.5051
CYP450 1A2 substrateNon-inhibitor0.6957
CYP450 2C9 inhibitorNon-inhibitor0.7771
CYP450 2D6 inhibitorNon-inhibitor0.8707
CYP450 2C19 inhibitorNon-inhibitor0.7064
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8916
Ames testNon AMES toxic0.7525
CarcinogenicityNon-carcinogens0.8816
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity1.6593 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9724
hERG inhibition (predictor II)Non-inhibitor0.8292
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-MSsplash10-00dl-3926000000-2148cf05d31b3658ebcf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0039100000-260c620a855a9a196eb2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9435000000-897e78cc7d827f5c45e5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-040r-0396100000-1c9524e8025d4f7b9a47
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6y-3229000000-dc17f33419e16f6f0be4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-e5c2b52e879c01b9c4c8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-008i-0419000000-87337a7a9023fa1c9d55
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]-207.0744637
predicted
DarkChem Lite v0.1.0
[M-H]-211.52013
predicted
DeepCCS 1.0 (2019)
[M+H]+205.7838637
predicted
DarkChem Lite v0.1.0
[M+H]+213.9157
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.7075637
predicted
DarkChem Lite v0.1.0
[M+Na]+219.85449
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring glycosyl groups
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
pbpA
Uniprot ID
Q8XJ01
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
75176.35 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. Cornaglia G, Ligozzi M, Bauernfeind A, Satta G, Fontana R: PBP binding and periplasmic concentration as determinants of the antibacterial activities of three new oral cephalosporins in Escherichia coli. New Microbiol. 1994 Jul;17(3):203-10. [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
  1. 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
  1. 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]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2024 11:06