Identification

Name
Ceftriaxone
Accession Number
DB01212  (APRD00395)
Type
Small Molecule
Groups
Approved
Description

A broad-spectrum cephalosporin antibiotic with a very long half-life and high penetrability to meninges, eyes and inner ears. [PubChem]

Structure
Thumb
Synonyms
  • (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefatriaxone
  • Ceftriaxona
  • Ceftriaxonum
  • Ceftriazone
Product Ingredients
IngredientUNIICASInChI Key
Ceftriaxone sodium023Z5BR09K104376-79-6PMRZKYOXTPBIQF-MAODNAKNSA-J
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceftriaxone and DextroseInjection, solution1 g/50mLIntravenousB. Braun Medical Inc.2005-04-20Not applicableUs
Ceftriaxone and DextroseInjection, solution2 g/50mLIntravenousB. Braun Medical Inc.2005-04-20Not applicableUs
Ceftriaxone for InjectionPowder, for solution2 gIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada
Ceftriaxone for InjectionPowder, for solution0.25 gIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada
Ceftriaxone for InjectionPowder, for solution100 gIntravenousFresenius Kabi2014-06-05Not applicableCanada
Ceftriaxone for InjectionPowder, for solution10 gIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada
Ceftriaxone for InjectionPowder, for solution0.5 gIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada
Ceftriaxone for InjectionPowder, for solution1 gIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada
Ceftriaxone for Injection USPPowder, for solution250 mgIntramuscular; IntravenousHospira, Inc.2008-04-10Not applicableCanada
Ceftriaxone for Injection USPPowder, for solution1 gIntramuscular; IntravenousSandoz Canada Incorporated2007-02-23Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CeftriaxoneInjection, solution1 g/50mLIntravenousBaxter Laboratories2005-08-23Not applicableUs
CeftriaxoneInjection, powder, for solution100 g/1IntravenousSamson Medical Technologies Llc2014-06-30Not applicableUs
CeftriaxoneInjection, powder, for solution10 g/1IntravenousAPP Pharmaceuticals, Inc.2011-06-20Not applicableUs
CeftriaxoneInjection, powder, for solution250 mg/1Intramuscular; IntravenousLupin Pharmaceuticals2009-06-01Not applicableUs
CeftriaxoneInjection, powder, for solution1 g/1Intramuscular; IntravenousSagent Pharmaceuticals2009-11-05Not applicableUs
CeftriaxoneInjection, powder, for solution100 mg/mLIntravenousApotex Corporation2005-08-02Not applicableUs
CeftriaxoneInjection, powder, for solution1 g/1IntravenousApotex Corporation2005-08-022017-11-01Us
CeftriaxoneInjection, powder, for solution250 mg/1Intramuscular; IntravenousWockhardt2007-04-12Not applicableUs
CeftriaxoneInjection, powder, for solution250 mg/1Intramuscular; IntravenousRemedy Repack2017-04-18Not applicableUs
CeftriaxoneInjection, powder, for solution2 g/1Intramuscular; IntravenousWest Ward Pharmaceutical2008-01-10Not applicableUs
International/Other Brands
Acantex (Roche) / Biotrakson (Bioton) / Rocephine (Roche)
Categories
UNII
75J73V1629
CAS number
73384-59-5
Weight
Average: 554.58
Monoisotopic: 554.04605704
Chemical Formula
C18H18N8O7S3
InChI Key
VAAUVRVFOQPIGI-SPQHTLEESA-N
InChI
InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][[email protected]]12SCC(CSC3=NC(=O)C(=O)NN3C)=C(N1C(=O)[[email protected]]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O

Pharmacology

Indication

For the treatment of the infections (respiratory, skin, soft tissue, UTI, ENT) caused by S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph

Structured Indications
Pharmacodynamics

Ceftriaxone is a cephalosporin/cephamycin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. Ceftriaxone has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ceftriaxone results from the inhibition of cell wall synthesis and is mediated through Ceftriaxone binding to penicillin binding proteins (PBPs). Ceftriaxone is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.

Mechanism of action

Ceftriaxone works by inhibiting the mucopeptide synthesis in the bacterial cell wall. The beta-lactam moiety of Ceftriaxone binds to carboxypeptidases, endopeptidases, and transpeptidases in the bacterial cytoplasmic membrane. These enzymes are involved in cell-wall synthesis and cell division. By binding to these enzymes, Ceftriaxone results in the formation of of defective cell walls and cell death.

TargetActionsOrganism
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
USolute carrier family 22 member 11Not AvailableHuman
USolute carrier family 22 member 6Not AvailableHuman
USolute carrier family 22 member 8Not AvailableHuman
USolute carrier family 15 member 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
  • 5.78 to 13.5 L
Protein binding

95%

Metabolism
Not Available
Route of elimination

Thirty-three percent to 67% of a ceftriaxone dose was excreted in the urine as unchanged drug and the remainder was secreted in the bile and ultimately found in the feces as microbiologically inactive compounds.

Half life

5.8-8.7 hours

Clearance
  • 0.58 - 1.45 L/h [healthy adults receiving 0.15-3 g of CEFTRIAXONE]
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Neisseria gonorrhoeae
  • Escherichia coli
  • Salmonella typhi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolCeftriaxone may increase the anticoagulant activities of Acenocoumarol.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ceftriaxone.Investigational
Calcium AcetateThe risk or severity of adverse effects can be increased when Calcium Acetate is combined with Ceftriaxone.Approved
Calcium CarbonateThe risk or severity of adverse effects can be increased when Calcium Carbonate is combined with Ceftriaxone.Approved
Calcium ChlorideThe risk or severity of adverse effects can be increased when Calcium Chloride is combined with Ceftriaxone.Approved
Calcium CitrateThe risk or severity of adverse effects can be increased when Calcium Citrate is combined with Ceftriaxone.Approved
Calcium glubionateThe risk or severity of adverse effects can be increased when Calcium glubionate is combined with Ceftriaxone.Approved
Calcium GluceptateThe risk or severity of adverse effects can be increased when Calcium Gluceptate is combined with Ceftriaxone.Approved
Calcium gluconateThe risk or severity of adverse effects can be increased when Calcium gluconate is combined with Ceftriaxone.Approved, Vet Approved
Calcium lactateThe risk or severity of adverse effects can be increased when Calcium lactate is combined with Ceftriaxone.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe risk or severity of adverse effects can be increased when Calcium lactate gluconate is combined with Ceftriaxone.Experimental
Calcium laevulateThe risk or severity of adverse effects can be increased when Calcium laevulate is combined with Ceftriaxone.Experimental
Calcium pangamateThe risk or severity of adverse effects can be increased when Calcium pangamate is combined with Ceftriaxone.Experimental
Calcium PhosphateThe risk or severity of adverse effects can be increased when Calcium Phosphate is combined with Ceftriaxone.Approved
CaseinThe risk or severity of adverse effects can be increased when Casein is combined with Ceftriaxone.Approved
ClorindioneCeftriaxone may increase the anticoagulant activities of Clorindione.Experimental
DicoumarolCeftriaxone may increase the anticoagulant activities of Dicoumarol.Approved
DiphenadioneCeftriaxone may increase the anticoagulant activities of Diphenadione.Experimental
Ethyl biscoumacetateCeftriaxone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCeftriaxone may increase the anticoagulant activities of Fluindione.Investigational
PhenindioneCeftriaxone may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonCeftriaxone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ceftriaxone.Approved
ProbenecidThe serum concentration of Ceftriaxone can be increased when it is combined with Probenecid.Approved
TioclomarolCeftriaxone may increase the anticoagulant activities of Tioclomarol.Experimental
WarfarinCeftriaxone may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Monguzzi Riccardo, Menaspace Silvano, Anzaghi Piergiorgio, "Process for the preparation of ceftriaxone." U.S. Patent US5026843, issued November, 1984.

US5026843
General References
Not Available
External Links
Human Metabolome Database
HMDB15343
KEGG Compound
C06683
PubChem Compound
5479530
PubChem Substance
46506458
ChemSpider
4586394
BindingDB
50049707
ChEBI
29007
ChEMBL
CHEMBL161
Therapeutic Targets Database
DAP000145
PharmGKB
PA448866
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ceftriaxone
ATC Codes
J01DD04 — CeftriaxoneJ01DD54 — Ceftriaxone, combinations
AHFS Codes
  • 08:12.06.12 — Third Generation Cephalosporins
FDA label
Download (211 KB)
MSDS
Download (53.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1, 2CompletedTreatmentHealthy Volunteers With Ileostomy1
1, 2Unknown StatusTreatmentPsychosis / Schizoaffective Disorders / Schizophrenic Disorders1
2Active Not RecruitingTreatmentMalnutrition1
2CompletedTreatmentCholangitis1
2CompletedTreatmentGonorrhoea1
2CompletedTreatmentLyme Disease / Lyme Neuroborreliosis1
2CompletedTreatmentPelvic Inflammatory Disease (PID)1
2CompletedTreatmentPneumonia, Bacterial2
2Not Yet RecruitingPreventionEndometritis1
2RecruitingTreatmentJaundice and Sepsis in Neonates1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
2Unknown StatusTreatmentHip Prosthetic Joint Infection1
2WithdrawnTreatmentBipolar Disorder (BD)1
2, 3CompletedBasic SciencePharmacokinetics in Healthy Adults1
2, 3CompletedTreatmentCommunity Acquired Pneumonia (CAP) / Infection NOS1
3Active Not RecruitingTreatmentEmergence of Bacterial Resistance to Antibiotics1
3CompletedDiagnosticLyme Neuroborreliosis1
3CompletedPreventionInfection NOS / Surgical Site Infections1
3CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
3CompletedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP) / Lung Infection of Individual Not Recently Hospitalized1
3CompletedTreatmentIntra-Abdominal Infections2
3CompletedTreatmentLyme Disease2
3CompletedTreatmentPneumonia3
3CompletedTreatmentPneumonia, Bacterial2
3CompletedTreatmentUncomplicated Urogenital Gonorrhea1
3CompletedTreatmentUrinary Tract Infections (UTIs)1
3Not Yet RecruitingTreatmentAntibiotic Resistance / Antibiotic Toxicity / Malnutrition Severe1
3RecruitingPreventionEarly Ventilation Acquired Pneumonia in Brain Injured Patients / Preventing Early VAP in Brain Injured Patients1
3RecruitingTreatmentAcute Male Urinary Tract Infection1
3RecruitingTreatmentGonorrhea1
3RecruitingTreatmentInfection Due to ESBL Escherichia Coli / Infection Due to Multidrug-resistant Escherichia Coli1
3RecruitingTreatmentPrimary Bacterial Peritonitis1
3RecruitingTreatmentSevere Septic Syndrome (Severe Sepsis and Septic Shock) Diagnosed and Treated by Mobile Intensive Care Unit1
3TerminatedTreatmentGonorrhea1
4Active Not RecruitingPreventionCalcium Nephrolithiasis / Urinary Tract Infections (UTIs)1
4Active Not RecruitingTreatmentInfection NOS1
4CompletedHealth Services ResearchMeningitis / Neurological Infections1
4CompletedPreventionEsophageal and Gastric Varices / Hemorrhage, Gastrointestinal1
4CompletedPreventionPneumonia1
4CompletedTreatmentAcute Uncomplicated Pyelonephritis1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)2
4CompletedTreatmentComplicated Intra-Abdominal Infections1
4CompletedTreatmentLiver Cirrhosis / SBP1
4CompletedTreatmentPneumonia1
4CompletedTreatmentPneumonia Ventilator Associated1
4CompletedTreatmentSalmonella Typhi Infection1
4CompletedTreatmentHepatic abscess1
4Not Yet RecruitingOtherPyelonephritis acute1
4Not Yet RecruitingTreatmentCritical Illness / Mechanical Ventilation Complication1
4Not Yet RecruitingTreatmentSevere Sepsis or Septic Shock1
4RecruitingTreatmentCholangitis1
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4TerminatedTreatmentPneumonia, Pneumococcal1
4Unknown StatusTreatmentDiarrhea1
4Unknown StatusTreatmentLyme Neuroborreliosis1
4Unknown StatusTreatmentSalmonella Typhi Infection1
4Unknown StatusTreatmentSepsis / Severe Sepsis / Shock, Septic1
Not AvailableActive Not RecruitingTreatmentCellulitis1
Not AvailableCompletedNot AvailableChlamydial Infections1
Not AvailableCompletedTreatmentGastroesophageal variceal hemorrhage prophylaxis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Neurosyphilis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Salmonella Infections1
Not AvailableCompletedTreatmentPerforated Appendicitis1
Not AvailableCompletedTreatmentSepsis / Severe Sepsis / Shock, Septic1
Not AvailableNot Yet RecruitingNot AvailableCommunity Acquired Pneumonia (CAP)1
Not AvailableNot Yet RecruitingNot AvailableNewborn; Infection1
Not AvailableRecruitingOtherNervous System Lyme Borreliosis1
Not AvailableRecruitingPreventionPropionibacterium infection1
Not AvailableRecruitingTreatmentLiver Abscess, Pyogenic1
Not AvailableRecruitingTreatmentMultiple Erythema Migrans1
Not AvailableTerminatedTreatmentDepression, Bipolar1
Not AvailableUnknown StatusTreatmentSuspected Early Lyme Neuroborreliosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntramuscular1 g/1
Injection, powder, for solutionIntramuscular1 g/10mL
Injection, powder, for solutionIntramuscular250 mg/1
Injection, powder, for solutionIntramuscular; Intravenous2 g/1
Injection, powder, for solutionIntramuscular; Intravenous250 mg/1
Injection, powder, for solutionIntramuscular; Intravenous500 mg/1
Injection, powder, for solutionIntravenous10 g/100mL
Injection, powder, for solutionIntravenous10 g/1
Injection, powder, for solutionIntravenous100 mg/mL
Injection, powder, for solutionIntravenous100 g/1
Injection, solutionIntravenous1 g/50mL
Injection, solutionIntravenous2 g/50mL
Powder, for solutionIntramuscular; Intravenous0.5 g
Powder, for solutionIntravenous100 g
Powder, for solutionIntramuscular; Intravenous0.25 g
Powder, for solutionIntramuscular; Intravenous10.0 g
Powder, for solutionIntramuscular; Intravenous2.0 g
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous2 g/1
Injection, powder, for solutionIntravenous500 mg/1
Powder, for solutionIntramuscular; Intravenous10 g
Powder, for solutionIntravenous10 g
Powder, for solutionIntramuscular; Intravenous1 g
Powder, for solutionIntramuscular; Intravenous2 g
Powder, for solutionIntramuscular; Intravenous250 mg
Powder, for solutionIntramuscular; Intravenous500 mg
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Powder, for solutionIntravenous1 g
Prices
Unit descriptionCostUnit
Rocephin 10 gm vial478.32USD vial
Rocephin 2 gm vial97.5USD vial
Ceftriaxone 2 gm piggyback94.17USD each
Rocephin 1 gm Solution Vial65.53USD vial
Rocephin 1 gm vial62.02USD vial
Ceftriaxone For Injection Usp 2 g/vial49.13USD vial
Ceftriaxone 1 gm piggyback47.91USD each
Rocephin 1 g/vial40.2USD vial
Ceftriaxone 10 gm vial36.25USD vial
Ceftriaxone 2 gm-d5w bag27.84USD each
Ceftriaxone For Injection Usp 1 g/vial24.93USD vial
Chloromycetin 1 g/vial20.33USD vial
Ceftriaxone 2 gm vial17.04USD vial
Ceftriaxone 1 gm-d5w bag13.92USD each
Rocephin 0.25 g/vial12.71USD vial
Ceftriaxone For Injection Usp 0.25 g/vial7.88USD vial
Ceftriaxone 1 gm vial7.56USD vial
Ceftriaxone sodium powder1.84USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>155 °CNot Available
logP-1.7Not Available
Caco2 permeability-6.88ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
logP-0.01ALOGPS
logP-1.8ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)4.17ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area208.98 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.47 m3·mol-1ChemAxon
Polarizability51.47 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.952
Blood Brain Barrier-0.9748
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.726
P-glycoprotein inhibitor INon-inhibitor0.8942
P-glycoprotein inhibitor IIInhibitor0.5293
Renal organic cation transporterNon-inhibitor0.8024
CYP450 2C9 substrateNon-substrate0.7943
CYP450 2D6 substrateNon-substrate0.8172
CYP450 3A4 substrateSubstrate0.5374
CYP450 1A2 substrateNon-inhibitor0.7538
CYP450 2C9 inhibitorNon-inhibitor0.7088
CYP450 2D6 inhibitorNon-inhibitor0.8666
CYP450 2C19 inhibitorNon-inhibitor0.7034
CYP450 3A4 inhibitorInhibitor0.6432
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5509
Ames testNon AMES toxic0.7336
CarcinogenicityNon-carcinogens0.8392
BiodegradationNot ready biodegradable0.9968
Rat acute toxicity2.1681 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9865
hERG inhibition (predictor II)Non-inhibitor0.6145
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / 2,4-disubstituted thiazoles / Alkylarylthioethers / 1,2,4-triazines / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids
show 12 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Aryl thioether / 2,4-disubstituted 1,3-thiazole / Alkylarylthioether / Meta-thiazine / 1,2,4-triazine / 1,3-thiazol-2-amine / Triazine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, 1,3-thiazole, oxime O-ether, 1,2,4-triazines (CHEBI:29007) / Cephems (C06683)

Targets

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
  1. Tomberg J, Unemo M, Davies C, Nicholas RA: Molecular and structural analysis of mosaic variants of penicillin-binding protein 2 conferring decreased susceptibility to expanded-spectrum cephalosporins in Neisseria gonorrhoeae: role of epistatic mutations. Biochemistry. 2010 Sep 21;49(37):8062-70. doi: 10.1021/bi101167x. [PubMed:20704258]
Kind
Protein
Organism
Human
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
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
Kind
Protein
Organism
Human
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
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
Kind
Protein
Organism
Human
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
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
Kind
Protein
Organism
Human
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
  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. [PubMed:15567297]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Manganese ion binding
Specific Function
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). E...
Gene Name
GLUL
Uniprot ID
P15104
Uniprot Name
Glutamine synthetase
Molecular Weight
42064.15 Da
References
  1. Tumani H, Smirnov A, Barchfeld S, Olgemoller U, Maier K, Lange P, Bruck W, Nau R: Inhibition of glutamine synthetase in rabbit pneumococcal meningitis is associated with neuronal apoptosis in the dentate gyrus. Glia. 2000 Mar;30(1):11-8. [PubMed:10696140]
  2. Verma R, Mishra V, Sasmal D, Raghubir R: Pharmacological evaluation of glutamate transporter 1 (GLT-1) mediated neuroprotection following cerebral ischemia/reperfusion injury. Eur J Pharmacol. 2010 Jul 25;638(1-3):65-71. doi: 10.1016/j.ejphar.2010.04.021. Epub 2010 Apr 24. [PubMed:20423712]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Other/unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Gulian JM, Dalmasso C, Gonard V: Interaction of beta-lactam antibiotics on bilirubin-albumin complex: comparison by three methods, total bilirubin, unbound bilirubin and erythrocyte-bound bilirubin. Chemotherapy. 1990;36(2):91-7. [PubMed:2311445]
  2. Nerli B, Farruggia B, Pico G: A comparative study of the binding characteristics of ceftriaxone, cefoperazone and cefsulodin to human serum albumin. Biochem Mol Biol Int. 1996 Nov;40(4):823-31. [PubMed:8950041]
  3. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:15567297]
Kind
Protein
Organism
Human
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. [PubMed:15567297]
Kind
Protein
Organism
Human
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
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172]
  3. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33