Identification

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

Cephalexin is the first of the first generation cephalosporins.7,8 This antibiotic contains a beta lactam and a dihydrothiazide.7 Cephalexin is used to treat a number of susceptible bacterial infections through inhibition of cell wall synthesis.9,Label Cephalexin was approved by the FDA on 4 January 1971.11

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-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CephalexinCapsule750 mg/1OralFera Pharmaceuticals, LLC2017-06-02Not applicableUs
Cephalexin Tab 250mgTablet250 mgOralPro Doc Limitee1989-12-312012-07-23Canada
Cephalexin-500Tablet500 mgOralPro Doc Limitee1989-12-31Not applicableCanada
KeflexCapsule750 mg/1OralPragma Pharmaceuticals, LLC2016-05-01Not applicableUs
KeflexTablet500 mgOralPendopharm Division Of De Pharmascience Inc1972-12-31Not applicableCanada
KeflexCapsule250 mg/1OralVictory Pharma, Inc.2010-12-312014-06-30Us
KeflexCapsule333 mg/1OralAdvancis Pharmaceutical Corporation2007-03-16Not applicableUs
KeflexCapsule500 mg/1OralShionogi1971-01-04Not applicableUs
KeflexCapsule500 mg/1OralPragma Pharmaceuticals, LLC2016-05-01Not applicableUs
KeflexPowder, for suspension250 mgOralPendopharm Division Of De Pharmascience Inc1971-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cephalexTablet250 mgOralApotex Corporation1988-12-31Not applicableCanada
Apo-cephalexTablet500 mgOralApotex Corporation1988-12-31Not applicableCanada
Auro-cephalexinTablet500 mgOralAuro Pharma IncNot applicableNot applicableCanada
Auro-cephalexinTablet250 mgOralAuro Pharma IncNot applicableNot applicableCanada
CephalexinCapsule500 mg/1OralDirectrx2017-02-20Not applicableUs
CephalexinCapsule500 mg/1Oralbryant ranch prepack2008-01-18Not applicableUs
CephalexinCapsule500 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2015-06-02Not applicableUs
CephalexinCapsule500 mg/1OralRpk Pharmaceuticals, Inc.1990-09-30Not applicableUs
CephalexinCapsule500 mg/1OralBlenheim Pharmacal, Inc.2009-12-22Not applicableUs
CephalexinCapsule500 mg/1OralDenton Pharma, Inc.2017-10-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O

Pharmacology

Indication

Cephalexin is indicated for the treatment of certain infections caused by susceptible bacteria.Label,12,13 These infections include respiratory tract infections, otitis media, skin and skin structure infections, bone infections, and genitourinary tract infections.Label,12,13

Associated Conditions
Pharmacodynamics

Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic.7,8 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.Label It is effective against most gram-positive bacteria through its inihibition of the cross linking reaction between N-acetyl muramicacid and N-acetylglucosamine in the cell wall, leading to cell lysis.9

Mechanism of action

Cephalexin is a first generation cephalosporin antibiotic.7,8 Cephalosporins contain a beta lactam and dihydrothiazide.7 Unlike penicillins, cephalosprins are more resistant to the action of beta lactamase.7 Cephalexin inhibits bacterial cell wall synthesis, leading breakdown and eventualy cell death.Label

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)
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Well absorbed from the upper gastrointestinal tract with nearly 100% oral bioavailability.3,4 Cephalexin is not absorbed in the stomach but is absorbed in the upper intestine.5

Patients taking 250mg of cephalexin reach a maximum plasma concentration of 7.7mcg/mL and patients taking 500mg reach 12.3mcg/mL.1

Volume of distribution

5.2-5.8L.6

Protein binding

Cephalexin is 10-15% bound to serum proteinsLabel,12 including serum albumin.[A179053]

Metabolism

Cephalexin is not metabolized in the body.2,Label,12,13

Route of elimination

Cephalexin is over 90% excreted in the urine after 6 hours1 by glomerular filtration and tubular secretionLabel,12,13 with a mean urinary recovery of 99.3%.3 Cephalexin is unchanged in the urine.1,2,3

Half life

The half life of cephalexin is 49.5 minutes in a fasted state and 76.5 minutes with food though these times were not significantly different in the study.3

Clearance

Clearance from one subject was 376mL/min.3

Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.Label An overdose is generally managed through supportive treatment as diuresis, dialysis, hemodialysis, and charcoal hemoperfusion are not well studied in this case.Label

The oral median lethal dose of cephalexin in rats is >5000 mg/kg. The oral LD50 in a monkey is >1g/kg and the lowest dose causing a toxic effect in humans is 14mg/kg.MSDS

Cephalexin has not been shown to be harmful in pregnancy and is not associated with teratogeniticy.Label Cephalexin is present in breast milk, though infants may be exposed to <1% of the dose given to the mother.Label The effects of breast milk exposure to cephalexin have not been established and so caution must be exercised and the risk and benefit of cephalexin use in breastfeeding must be weighed.Label

Cephalexin has not been studied for carcinogenicity or mutagenicity.Label Cephalexin has no affect on fertility in rats.Label

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Cephalexin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Cephalexin is combined with (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Cephalexin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Cephalexin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Cephalexin.
6-Deoxyerythronolide BThe metabolism of Cephalexin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Cephalexin.
7-ethyl-10-hydroxycamptothecinThe metabolism of Cephalexin can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Cephalexin.
AbacavirCephalexin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Evidence Level

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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
  1. Thornhill TS, Levison ME, Johnson WD, Kaye D: In vitro antimicrobial activity and human pharmacology of cephalexin, a new orally absorbed cephalosporin C antibiotic. Appl Microbiol. 1969 Mar;17(3):457-61. [PubMed:4388601]
  2. Sullivan HR, Billings RE, McMahon RE: Metabolism of cephalexin-14C in mice and in rats. J Antibiot (Tokyo). 1969 May;22(5):195-200. [PubMed:5811391]
  3. Gower PE, Dash CH: Cephalexin: human studies of absorption and excretion of a new cephalosporin antibiotic. Br J Pharmacol. 1969 Nov;37(3):738-47. doi: 10.1111/j.1476-5381.1969.tb08513.x. [PubMed:5348475]
  4. Henning C, Kallings LO, Lidman K, Sterner G: Studies of absorption, excretion, antibacterial and clinical effect of cephalexin. Scand J Infect Dis. 1970;2(2):131-8. [PubMed:4398634]
  5. Griffith RS: The pharmacology of cephalexin. Postgrad Med J. 1983;59 Suppl 5:16-27. [PubMed:6364086]
  6. Pfeffer M, Jackson A, Ximenes J, de Menezes JP: Comparative human oral clinical pharmacology of cefadroxil, cephalexin, and cephradine. Antimicrob Agents Chemother. 1977 Feb;11(2):331-8. doi: 10.1128/aac.11.2.331. [PubMed:848940]
  7. Tanrisever B, Santella PJ: Cefadroxil. A review of its antibacterial, pharmacokinetic and therapeutic properties in comparison with cephalexin and cephradine. Drugs. 1986;32 Suppl 3:1-16. doi: 10.2165/00003495-198600323-00003. [PubMed:3542485]
  8. Sader HS, Jacobs MR, Fritsche TR: Review of the spectrum and potency of orally administered cephalosporins and amoxicillin/clavulanate. Diagn Microbiol Infect Dis. 2007 Mar;57(3 Suppl):5S-12S. doi: 10.1016/j.diagmicrobio.2006.12.014. Epub 2007 Feb 9. [PubMed:17292577]
  9. Fisher JF, Meroueh SO, Mobashery S: Bacterial resistance to beta-lactam antibiotics: compelling opportunism, compelling opportunity. Chem Rev. 2005 Feb;105(2):395-424. doi: 10.1021/cr030102i. [PubMed:15700950]
  10. Cephalexin Product Monograph [Link]
  11. FDA Approved Drug Products: Cephalexin Oral Capsule [Link]
  12. FDA Approved Drug Products: Cephalexin Oral Suspension [Link]
  13. FDA Approved Drug Products: Cephalexin Oral Tablet [Link]
External Links
Human Metabolome Database
HMDB0014707
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
Wikipedia
Cephalexin
ATC Codes
J01DB01 — Cefalexin
AHFS Codes
  • 08:12.06.04 — First Generation Cephalosporins
FDA label
Download (133 KB)
MSDS
Download (25.4 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 RecruitingBasic ScienceOsteomyelitis / Pyomyositis / Septic Arthritis1
1RecruitingTreatmentSurgical Site Infection Rate / Surgical Site Infection Rate in Obese Women Who Have Labored Undergoing Cesarean Section / Surgical Site Infections1
1TerminatedTreatmentUrinary Bladder, Overactive1
1, 2CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1, 2RecruitingTreatmentCancer of the Gastrointestinal Tract / Cancer of Unknown Origin1
2CompletedTreatmentCellulitis1
2CompletedTreatmentFinger Injuries1
2CompletedTreatmentSurgical Site Infections1
2RecruitingTreatmentAtopic Dermatitis (AD)1
2RecruitingTreatmentUrinary Tract Infections (UTIs)1
2, 3CompletedTreatmentInfection caused by staphylococci1
3CompletedPreventionArrythmias1
3TerminatedTreatmentBladder Cancers1
4Active Not RecruitingPreventionArrythmias1
4CompletedTreatmentAbscesses / Folliculitis / Infection caused by staphylococci / Staphylococcal Skin Infections1
4CompletedTreatmentMild to Moderate Uncomplicated Skin and Skin Structure Infections1
4RecruitingPreventionRenal Stones1
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 AvailableNot Yet RecruitingPreventionSurgical Site Infections1
Not AvailableNot Yet RecruitingPreventionCutaneous lesions1
Not AvailableTerminatedTreatmentBacteriuria (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
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Altura Pharmaceuticals Inc.
  • Amkas Laboratories Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Carlsbad Technology Inc.
  • Central Texas Community Health Centers
  • Ceph International Corp.
  • Comprehensive Consultant Services Inc.
  • Darby Dental Supply Co. Inc.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Dorx LLC
  • Eli Lilly & Co.
  • Gen Source Rx
  • Golden State Medical Supply Inc.
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Institut Biochemique SA
  • International Ethical Labs Inc.
  • Jazeera Pharmaceutical Industries
  • Keltman Pharmaceuticals Inc.
  • Levista Inc.
  • Liberty Pharmaceuticals
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Medvantx Inc.
  • Middlebrook Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patheon Inc.
  • Patient First Corp.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Stat Rx Usa
  • Stat Scripts LLC
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Vedco Inc.
  • West-Ward Pharmaceuticals
  • World Gen LLC
  • Yung Shin Pharmaceutical Industry Ltd.
Dosage forms
FormRouteStrength
For suspensionOral125 mg/5mL
For suspensionOral250 mg/5mL
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
TabletOral250 mg/1
TabletOral500 mg/1
SuspensionOral125 mg/5mL
SuspensionOral250 mg/5mL
CapsuleOral250 mg/1
CapsuleOral333 mg/1
CapsuleOral500 mg/1
CapsuleOral750 mg/1
Powder, for suspensionOral250 mg
Tablet, solubleOral125 mg/1
Tablet, solubleOral250 mg/1
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 °Chttp://www.chemspider.com/Chemical-Structure.25541.html
boiling point (°C)727.4http://www.chemspider.com/Chemical-Structure.25541.html
water solubility10mg/mLhttp://www.chemspider.com/Chemical-Structure.25541.html
logP0.65HANSCH,C ET AL. (1995)
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]

Carriers

Kind
Protein
Organism
Humans
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]
  2. Nerli B, Romanini D, Pico G: Structural specificity requirements in the binding of beta lactam antibiotics to human serum albumin. Chem Biol Interact. 1997 May 2;104(2-3):179-202. [PubMed:9212783]

Transporters

Kind
Protein
Organism
Humans
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
Humans
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
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. 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
Humans
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
Humans
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]
  2. Motohashi H, Inui K: Organic cation transporter OCTs (SLC22) and MATEs (SLC47) in the human kidney. AAPS J. 2013 Apr;15(2):581-8. doi: 10.1208/s12248-013-9465-7. Epub 2013 Feb 22. [PubMed:23435786]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  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]

Drug created on June 13, 2005 07:24 / Updated on May 23, 2019 16:48