Identification

Name
Cephalexin
Accession Number
DB00567  (APRD00250)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of cephaloridine or cephalothin, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.

Structure
Thumb
Synonyms
  • (6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanic acid
  • 7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid
  • Anhydrous cefalexin
  • Anhydrous cephalexin
  • Cefalexin
  • Cefalexin anhydrous
  • Cefalexina
  • Céfalexine
  • Cefalexinum
  • Cephalexin anhydrous
External IDs
LILLY-66873 / S-6437
Product Ingredients
IngredientUNIICASInChI Key
Cefalexin hydrochloride6VJE5G3D98105879-42-3YHJDZIQOCSDIQU-OEDJVVDHSA-N
Cefalexin monohydrateOBN7UDS42Y23325-78-2AVGYWQBCYZHHPN-CYJZLJNKSA-N
Cefalexin sodiumF78YJG0WXK38932-40-0NZDYPHVJLWMLJI-CYJZLJNKSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CephalexinCapsule750 mg/1OralFera Pharmaceuticals2017-06-02Not applicableUs
Cephalexin Tab 250mgTablet250 mgOralPro Doc Limitee1989-12-312012-07-23Canada
Cephalexin Tab 500mgTablet500 mgOralPro Doc Limitee1989-12-31Not applicableCanada
Dom-cephalexin - Tab 250mgTablet250 mgOralDominion Pharmacal1995-12-31Not applicableCanada
Dom-cephalexin - Tab 500mgTablet500 mgOralDominion Pharmacal1995-12-31Not applicableCanada
Dom-cephalexin 125 - Sus 125mg/5mlSuspension125 mgOralDominion Pharmacal1995-12-31Not applicableCanada
Dom-cephalexin 250 - Sus 250mg/5mlSuspension250 mgOralDominion Pharmacal1995-12-31Not applicableCanada
KeflexPowder, for suspension125 mgOralPendopharm Division Of De Pharmascience Inc1971-12-31Not applicableCanada
KeflexCapsule250 mg/1OralShionogi1971-01-04Not applicableUs
KeflexCapsule500 mg/1OralPragma Pharmaceuticals, LLC2016-05-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cephalexTablet500 mgOralApotex Corporation1988-12-31Not applicableCanada
Apo-cephalexTablet250 mgOralApotex Corporation1988-12-31Not applicableCanada
CephalexinPowder, for suspension125 mg/5mLOralA S Medication Solutions1990-09-302017-06-20Us
CephalexinFor suspension250 mg/5mLOralLake Erie Medical Dba Quality Care Produts Llc2006-01-11Not applicableUs
CephalexinCapsule250 mg/1OralGolden State Medical Supply2011-01-28Not applicableUs
CephalexinSuspension125 mg/5mLOralWest Ward Pharmaceutical2009-09-01Not applicableUs
CephalexinCapsule500 mg/1OralAscend Laboratories, LLC2011-01-19Not applicableUs
CephalexinCapsule250 mg/1OralBlenheim Pharmacal, Inc.2012-01-19Not applicableUs
CephalexinCapsule500 mg/1OralNorthwind Pharmaceuticals2014-06-17Not applicableUs
CephalexinFor suspension250 mg/5mLOralAidarex Pharmaceuticals LLC2006-01-11Not applicableUs
International/Other Brands
Alcephin (Alembic) / Alexin (Dabur) / Alsporin (Renata) / Cefadin (Life) / Cefalin (BioFemme) / Ceforal (Teva) / Cefovit (Vitamed) / Celexin (Atlantic) / Cephin (General Drugs House) / Ceporexin (Investi) / Felexin (Remedica) / Ibilex (Alphapharm) / Keforal (Saiph) / L-Keflex (Shionogi Seiyaku) / Larixin (Taisho Yakuhin) / Lonflex (Union) / Madlexin (Meiji) / Nufex (General Pharma) / Oriphex (Maydsm Trading) / Ospexin (Sandoz) / Palitrex (Galenika) / Pyassan (Sanofi) / Sanaxin (Sandoz) / Sencephalin (Takeda Pharmaceutical) / Sepexin (Hetero) / Servispor (Sandoz) / Sialexin (Siam Bheasach) / Sporicef (Ranbaxy) / Sporidex (Ranbaxy) / Syncl (Asahi Kasei Pharma) / Tepaxin (Takeda) / Uphalexin (CCM) / Voxxim (Roddensers) / Winlex (Winston)
Categories
UNII
5SFF1W6677
CAS number
15686-71-2
Weight
Average: 347.389
Monoisotopic: 347.093976737
Chemical Formula
C16H17N3O4S
InChI Key
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
InChI
InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
IUPAC Name
(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][[email protected]]12SCC(C)=C(N1C(=O)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=CC=C1)C(O)=O

Pharmacology

Indication

For the treatment of respiratory tract infections caused by Streptococcus pneumoniae and Streptococcus pyogenes; otitis media due to Streptococcus pneumoniae, Haemophilus influenzae, Staphylococcus aureus, Streptococcus pyogenes, and Moraxella catarrhalis; skin and skin structure infections caused by Staphylococcus aureus and/or Streptococcus pyogenes; bone infections caused by Staphylococcus aureus and/or Proteus mirabilis; genitourinary tract infections, including acute prostatitis, caused by Escherichia coli, Proteus mirabilis, and Klebsiella pneumoniae.

Structured Indications
Pharmacodynamics

Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic. It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations. It is effective against most gram-positive bacteria.

Mechanism of action

Cephalexin, 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 cephalexin interferes with an autolysin inhibitor.

TargetActionsOrganism
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Absorption

Well absorbed from the gastrointestinal tract

Volume of distribution
Not Available
Protein binding

14%

Metabolism

No appreciable biotransformation in the liver (90% of the drug is excreted unchanged in the urine).

Route of elimination

Cephalexin is excreted in the urine by glomerular filtration and tubular secretion. Studies showed that over 90% of the drug was excreted unchanged in the urine within 8 hours.

Half life

1 hour

Clearance
Not Available
Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting. The oral median lethal dose of cephalexin in rats is >5000 mg/kg.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Cephalexin can be increased when it is combined with Abiraterone.Approved
AcenocoumarolCephalexin may increase the anticoagulant activities of Acenocoumarol.Approved
AmiodaroneThe metabolism of Cephalexin can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Cephalexin can be increased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe metabolism of Cephalexin can be decreased when combined with Artemether.Approved
AtazanavirThe metabolism of Cephalexin can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Cephalexin can be decreased when combined with Atomoxetine.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Cephalexin.Investigational
BetaxololThe metabolism of Cephalexin can be decreased when combined with Betaxolol.Approved
BoceprevirThe metabolism of Cephalexin can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Cephalexin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Cephalexin can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Cephalexin can be decreased when combined with Bupropion.Approved
CarbamazepineThe metabolism of Cephalexin can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Cephalexin can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Cephalexin can be increased when it is combined with Ceritinib.Approved
ChloroquineThe metabolism of Cephalexin can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Cephalexin can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Cephalexin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Cephalexin can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Cephalexin can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Cephalexin can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Cephalexin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Cephalexin can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Cephalexin can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Cephalexin can be decreased when combined with Clomipramine.Approved, Vet Approved
ClorindioneCephalexin may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Cephalexin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Cephalexin can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Cephalexin can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Cephalexin can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Cephalexin can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Cephalexin can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Cephalexin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Cephalexin can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Cephalexin can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Cephalexin can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Cephalexin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Cephalexin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Cephalexin can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Cephalexin can be decreased when combined with Desipramine.Approved
DicoumarolCephalexin may increase the anticoagulant activities of Dicoumarol.Approved
DihydroergotamineThe metabolism of Cephalexin can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Cephalexin can be decreased when combined with Diltiazem.Approved
DiphenadioneCephalexin may increase the anticoagulant activities of Diphenadione.Experimental
DiphenhydramineThe metabolism of Cephalexin can be decreased when combined with Diphenhydramine.Approved
DosulepinThe metabolism of Cephalexin can be decreased when combined with Dosulepin.Approved
DoxycyclineThe metabolism of Cephalexin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Cephalexin can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Cephalexin can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Cephalexin can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Cephalexin can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Cephalexin can be decreased when combined with Erythromycin.Approved, Vet Approved
Ethyl biscoumacetateCephalexin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluconazoleThe metabolism of Cephalexin can be decreased when combined with Fluconazole.Approved
FluindioneCephalexin may increase the anticoagulant activities of Fluindione.Investigational
FluoxetineThe metabolism of Cephalexin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Cephalexin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Cephalexin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Cephalexin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Cephalexin can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Cephalexin can be increased when it is combined with Fusidic Acid.Approved
HaloperidolThe metabolism of Cephalexin can be decreased when combined with Haloperidol.Approved
IdelalisibThe serum concentration of Cephalexin can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Cephalexin can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Cephalexin can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Cephalexin can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Cephalexin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Cephalexin can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Cephalexin can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Cephalexin can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Cephalexin can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Cephalexin can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Cephalexin can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Cephalexin can be decreased when combined with Lorcaserin.Approved
LovastatinThe metabolism of Cephalexin can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Cephalexin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Cephalexin can be increased when combined with Lumacaftor.Approved
LumefantrineThe metabolism of Cephalexin can be decreased when combined with Lumefantrine.Approved
ManidipineThe metabolism of Cephalexin can be decreased when combined with Manidipine.Approved
MetforminThe serum concentration of Metformin can be increased when it is combined with Cephalexin.Approved
MethadoneThe metabolism of Cephalexin can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Cephalexin can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Cephalexin can be decreased when combined with Metoprolol.Approved, Investigational
MidostaurinThe metabolism of Cephalexin can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Cephalexin can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Cephalexin can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Cephalexin can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Cephalexin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Cephalexin can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Cephalexin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Cephalexin can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Cephalexin can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Cephalexin can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Cephalexin can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Cephalexin can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Cephalexin can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Cephalexin can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Cephalexin can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Cephalexin can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Cephalexin can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenindioneCephalexin may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Cephalexin can be increased when combined with Phenobarbital.Approved
PhenprocoumonCephalexin may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe metabolism of Cephalexin can be increased when combined with Phenytoin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cephalexin.Approved
PosaconazoleThe metabolism of Cephalexin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Cephalexin can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Cephalexin can be increased when it is combined with Probenecid.Approved
PromazineThe metabolism of Cephalexin can be decreased when combined with Promazine.Approved, Vet Approved
QuinidineThe metabolism of Cephalexin can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Cephalexin can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Cephalexin can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Cephalexin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Cephalexin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Cephalexin can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Cephalexin can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Cephalexin can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Cephalexin can be decreased when combined with Ropinirole.Approved, Investigational
SaquinavirThe metabolism of Cephalexin can be decreased when combined with Saquinavir.Approved, Investigational
SertralineThe metabolism of Cephalexin can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Cephalexin can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Cephalexin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Cephalexin can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Cephalexin can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Cephalexin can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Cephalexin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Cephalexin can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Cephalexin can be decreased when combined with Telithromycin.Approved
TerbinafineThe metabolism of Cephalexin can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Cephalexin can be increased when it is combined with Teriflunomide.Approved
ThioridazineThe metabolism of Cephalexin can be decreased when combined with Thioridazine.Withdrawn
TiclopidineThe metabolism of Cephalexin can be decreased when combined with Ticlopidine.Approved
TioclomarolCephalexin may increase the anticoagulant activities of Tioclomarol.Experimental
TipranavirThe metabolism of Cephalexin can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Cephalexin can be decreased when it is combined with Tocilizumab.Approved
TranylcypromineThe metabolism of Cephalexin can be decreased when combined with Tranylcypromine.Approved
VenlafaxineThe metabolism of Cephalexin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Cephalexin can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Cephalexin can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinCephalexin may increase the anticoagulant activities of Warfarin.Approved
ZiprasidoneThe metabolism of Cephalexin can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals.

References

Synthesis Reference

Peter Faarup, "Method of preparing a sparingly soluble complex of cephalexin." U.S. Patent US4003896, issued May, 1975.

US4003896
General References
Not Available
External Links
Human Metabolome Database
HMDB14707
KEGG Drug
D00263
KEGG Compound
C06895
PubChem Compound
27447
PubChem Substance
46506749
ChemSpider
25541
BindingDB
50139896
ChEBI
3534
ChEMBL
CHEMBL1727
Therapeutic Targets Database
DAP000437
PharmGKB
PA448883
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cephalexin
ATC Codes
J01DB01 — Cefalexin
AHFS Codes
  • 08:12.06.04 — First Generation Cephalosporins
FDA label
Download (2.1 MB)
MSDS
Download (93.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableRespiratory Tract Infections (RTI)1
1CompletedBasic ScienceHealthy Volunteers5
1CompletedOtherRespiratory Tract Infections (RTI)2
1CompletedTreatmentAnti-Infective Agents3
1Not Yet RecruitingTreatmentSurgical Site Infection Rate in Obese Women Who Have Labored Undergoing Cesarean Section1
1TerminatedTreatmentOveractive Bladder / Overactive Urinary Bladder1
2CompletedTreatmentCellulitis1
2CompletedTreatmentFinger Injuries1
2CompletedTreatmentSurgical Site Infections1
2RecruitingTreatmentAtopic Dermatitis (AD)1
2RecruitingTreatmentUrinary Tract Infections (UTIs)1
2, 3CompletedTreatmentInfection caused by staphylococci1
3CompletedPreventionArrythmias1
3RecruitingTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious1
3TerminatedTreatmentBladder Cancers1
4Active Not RecruitingPreventionArrythmias1
4CompletedTreatmentAbscesses / Folliculitis / Infection caused by staphylococci / Staphylococcal Skin Infections1
4CompletedTreatmentMild to Moderate Uncomplicated Skin and Skin Structure Infections1
4RecruitingTreatmentFacial Defect1
4Unknown StatusTreatmentClean Laceration / Hand Laceration / No Bone Involved / Tendon Involved1
4WithdrawnPreventionComplications; Breast Prosthesis, Infection or Inflammation1
Not AvailableCompletedNot AvailableDrug Half Life / Pharmacokinetics / Placebo Effect1
Not AvailableCompletedPreventionElective Cesarean Section1
Not AvailableCompletedTreatmentCellulitis1
Not AvailableCompletedTreatmentSnoring / Strep Throat1
Not AvailableCompletedTreatmentSoft Tissues Infections1
Not AvailableRecruitingTreatmentBacteriuria (Asymptomatic) in Pregnancy1
Not AvailableTerminatedTreatmentSimple Hand Lacerations1
Not AvailableTerminatedTreatmentThrough-and-through Lip Lacerations1
Not AvailableUnknown StatusPreventionDentofacial Deformity1
Not AvailableUnknown StatusPreventionSurgical Site Infection in Obese Women Undergoing C-section1

Pharmacoeconomics

Manufacturers
  • Acs dobfar info sa
  • Apothecon inc div bristol myers squibb
  • Aurobindo pharma ltd inc
  • Barr laboratories inc
  • Belcher pharmaceuticals inc
  • Hikma pharmaceuticals
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lupin ltd
  • Orchid healthcare
  • Purepac pharmaceutical co
  • Ranbaxy laboratories ltd
  • Jerome stevens pharmaceuticals inc
  • Sun pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Yoshitomi pharmaceutical industries ltd
  • Yung shin pharmaceutical industrial co ltd
  • Middlebrook pharmaceuticals inc
  • Vitarine pharmaceuticals inc
  • Lex pharmaceuticals inc
  • Eli lilly and co
Packagers
Dosage forms
FormRouteStrength
CapsuleOral250 mg/1
CapsuleOral500 mg/1
For suspensionOral125 mg/5mL
For suspensionOral250 mg/5mL
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
SuspensionOral125 mg/5mL
SuspensionOral250 mg/5mL
TabletOral250 mg/1
TabletOral500 mg/1
CapsuleOral333 mg/1
CapsuleOral750 mg/1
Powder, for suspensionOral250 mg
SuspensionOral125 mg
SuspensionOral250 mg
CapsuleOral250 mg
CapsuleOral500 mg
TabletOral250 mg
TabletOral500 mg
Powder, for suspensionOral125 mg
Prices
Unit descriptionCostUnit
Cephalexin 250 mg/5ml Suspension 200ml Bottle32.76USD bottle
Cephalexin 250 mg/5ml Suspension 100ml Bottle19.66USD bottle
Cephalexin 125 mg/5ml Suspension 200ml Bottle16.39USD bottle
Cephalexin 125 mg/5ml Suspension 100ml Bottle15.99USD bottle
Keflex 500 mg capsule5.75USD capsule
Keflex 500 mg pulvule4.99USD each
Keflex 750 mg capsule3.34USD capsule
Cephalexin 500 mg tablet2.25USD tablet
Keflex 250 mg capsule2.2USD capsule
Keflex 250 mg pulvule1.85USD each
Cephalexin 500 mg capsule1.4USD capsule
Cephalexin 250 mg tablet1.17USD tablet
Cephalexin 250 mg capsule0.72USD capsule
Apo-Cephalex 500 mg Tablet0.47USD tablet
Novo-Lexin 500 mg Capsule0.47USD capsule
Novo-Lexin 500 mg Tablet0.47USD tablet
Nu-Cephalex 500 mg Tablet0.47USD tablet
Apo-Cephalex 250 mg Tablet0.24USD tablet
Novo-Lexin 250 mg Capsule0.24USD capsule
Novo-Lexin 250 mg Tablet0.24USD tablet
Nu-Cephalex 250 mg Tablet0.24USD tablet
Novo-Lexin 50 mg/ml Suspension0.14USD ml
Novo-Lexin 25 mg/ml Suspension0.09USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)326.8 °CNot Available
water solubility1.789 mg/mL as monohydrate salt (solubility in water is low at room temperature; 1 or 2 mg/mL may be dissolved readily, but higher concentrations are obtained with increasing difficulty)FDA Label
logP0.65HANSCH,C ET AL. (1995)
pKa4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.297 mg/mLALOGPS
logP0.55ALOGPS
logP-2.1ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.97 m3·mol-1ChemAxon
Polarizability32.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7537
Blood Brain Barrier-0.996
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.786
P-glycoprotein inhibitor INon-inhibitor0.9033
P-glycoprotein inhibitor IINon-inhibitor0.9921
Renal organic cation transporterNon-inhibitor0.9485
CYP450 2C9 substrateNon-substrate0.8011
CYP450 2D6 substrateNon-substrate0.8308
CYP450 3A4 substrateNon-substrate0.5289
CYP450 1A2 substrateNon-inhibitor0.9242
CYP450 2C9 inhibitorNon-inhibitor0.9251
CYP450 2D6 inhibitorNon-inhibitor0.9359
CYP450 2C19 inhibitorNon-inhibitor0.922
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9303
Ames testNon AMES toxic0.6834
CarcinogenicityNon-carcinogens0.8861
BiodegradationNot ready biodegradable0.9812
Rat acute toxicity1.2715 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9971
hERG inhibition (predictor II)Non-inhibitor0.8686
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ab9-0900000000-e1976a2fc84f1a3ef783

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 / Alpha amino acid amides / Phenylacetamides / Aralkylamines / 1,3-thiazines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives
show 9 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Aralkylamine / Meta-thiazine / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:3534)

Targets

Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not Available
Gene Name
pbp3
Uniprot ID
Q75Y35
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
45209.84 Da
References
  1. 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. [PubMed:7447421]
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
  1. 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. [PubMed:7447421]
  2. Mitsuoka K, Kato Y, Kubo Y, Tsuji A: Functional expression of stereoselective metabolism of cephalexin by exogenous transfection of oligopeptide transporter PEPT1. Drug Metab Dispos. 2007 Mar;35(3):356-62. Epub 2006 Dec 1. [PubMed:17142565]
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
  1. 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. [PubMed:7447421]
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. 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. [PubMed:7447421]
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
  1. 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. [PubMed:7447421]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

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. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Liang R, Fei YJ, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH: Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization. J Biol Chem. 1995 Mar 24;270(12):6456-63. [PubMed:7896779]
  2. Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [PubMed:8627565]
  3. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326]
  4. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994]
  5. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037]
  6. 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]
  7. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
  8. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745]
  9. Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A: The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine. J Pharm Pharmacol. 1997 Aug;49(8):796-801. [PubMed:9379359]
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. Liu W, Liang R, Ramamoorthy S, Fei YJ, Ganapathy ME, Hediger MA, Ganapathy V, Leibach FH: Molecular cloning of PEPT 2, a new member of the H+/peptide cotransporter family, from human kidney. Biochim Biophys Acta. 1995 May 4;1235(2):461-6. [PubMed:7756356]
  2. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745]
  3. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
  4. 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
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. 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]
  2. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
  3. Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [PubMed:15618660]
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. 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
Substrate
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Watanabe S, Tsuda M, Terada T, Katsura T, Inui K: Reduced renal clearance of a zwitterionic substrate cephalexin in MATE1-deficient mice. J Pharmacol Exp Ther. 2010 Aug;334(2):651-6. doi: 10.1124/jpet.110.169433. Epub 2010 May 19. [PubMed:20484555]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2017 14:13