Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H17N3O4S.2C3H7NO |
| Molecular Weight | 493.576 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C=O.CN(C)C=O.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(O)=O
InChI
InChIKey=YBXKLAPBAGZWTL-OEDJVVDHSA-N
InChI=1S/C16H17N3O4S.2C3H7NO/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;2*1-4(2)3-5/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);2*3H,1-2H3/t10-,11-,15-;;/m1../s1
| Molecular Formula | C16H17N3O4S |
| Molecular Weight | 347.389 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C3H7NO |
| Molecular Weight | 73.0938 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Cephalexin is a semisynthetic cephalosporin antibiotic intended for
oral administration. In vitro tests demonstrate that the cephalosporins are bactericidal because of their inhibition of cell-wall synthesis. Cephalexin has been shown to be active against most strains of the following microorganisms both in vitro: Staphylococcus aureus (including penicillinase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains), Streptococcus pyogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Moraxella (Branhamella) catarrhalis, Proteus mirabilis. Cephalexin is indicated for the treatment of the respiratory tract, skin and skin structure, bone and genitourinary tract infections when caused by susceptible strains of the designated microorganisms.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2354204 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | KEFLEX Approved UseCephalexin capsules are indicated for the treatment of the following infections when caused by susceptible strains of the designated microorganisms: Respiratory tract infections caused by Streptococcus pneumoniae and Streptococcus pyogenes (Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cephalexin capsules are generally effective in the eradication of streptococci from the nasopharynx; however, substantial data establishing the efficacy of cephalexin capsules in the subsequent prevention of rheumatic fever are not available at present.) 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 Note — Culture and susceptibility tests should be initiated prior to and during therapy. Renal function studies should be performed when indicated. To reduce the development of drug-resistant bacteria and maintain the effectiveness of cephalexin and other antibacterial drugs, cephalexin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1971 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18.25 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALEXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
126 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23811740 |
40 mg/kg 3 times / day multiple, oral dose: 40 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
CEPHALEXIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
31.22 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALEXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
245 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23811740 |
40 mg/kg 3 times / day multiple, oral dose: 40 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
CEPHALEXIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALEXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALEXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
40 mg/kg 3 times / day multiple, oral (median) Dose: 40 mg/kg, 3 times / day Route: oral Route: multiple Dose: 40 mg/kg, 3 times / day Sources: |
unhealthy, 1-16 years n = 12 Health Status: unhealthy Condition: Osteoarticular Infections Age Group: 1-16 years Sex: M+F Population Size: 12 Sources: |
Disc. AE: Neutropenia... AEs leading to discontinuation/dose reduction: Neutropenia (1 patient) Sources: |
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 90 years n = 1 Health Status: unhealthy Age Group: 90 years Sex: F Population Size: 1 Sources: |
Disc. AE: Tendonitis... AEs leading to discontinuation/dose reduction: Tendonitis (1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Neutropenia | 1 patient Disc. AE |
40 mg/kg 3 times / day multiple, oral (median) Dose: 40 mg/kg, 3 times / day Route: oral Route: multiple Dose: 40 mg/kg, 3 times / day Sources: |
unhealthy, 1-16 years n = 12 Health Status: unhealthy Condition: Osteoarticular Infections Age Group: 1-16 years Sex: M+F Population Size: 12 Sources: |
| Tendonitis | 1 patient Disc. AE |
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, 90 years n = 1 Health Status: unhealthy Age Group: 90 years Sex: F Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Current issues in antimicrobial therapy for the treatment of acne. | 2001 |
|
| Synthesis and antibacterial activity of 5-nitrofuryl and 3-methoxy-2-nitrophenyl derivatives of 6 beta-aminopenicillanic, 7 beta-aminocephalosporanic and 7 beta-aminodesacetoxy-cephalosporanic acids. | 2001 |
|
| Drug inhibition of Gly-Sar uptake and hPepT1 localization using hPepT1-GFP fusion protein. | 2001 |
|
| Upper respiratory tract infections. | 2001 Dec |
|
| Skin and soft tissue infection. | 2001 Jul |
|
| Introduction of recirculatory analysis into portal and systemic concentration difference method. | 2001 Nov |
|
| Consensus statement on management of antenatally detected hydronephrosis. | 2001 Nov |
|
| [The use of veterinary drugs during pregnancy of the dog]. | 2001 Nov 15 |
|
| Ocular pharmacokinetics of cephalosporins using microdialysis. | 2001 Oct |
|
| Equal allergenic potency of beta-lactam antibiotics produced by chemical or enzymatic manufacturing--mouse IgE test. | 2001 Oct |
|
| Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
|
| Determination of cephalexin in oral suspensions by micellar electrokinetic chromatography. | 2002 |
|
| Moxifloxacin in uncomplicated skin and skin structure infections. | 2002 |
|
| Prophylactic antibiotics in cirrhotics with upper gastrointestinal hemorrhage: a prospective, controlled trial. | 2002 Aug |
|
| Localized lymphatic sporotrichosis after fish-induced injury (Tilapia sp.). | 2002 Aug |
|
| Infantile pertussis rediscovered in China. | 2002 Aug |
|
| Immunoglobulin E binding determinants on beta-lactam drugs. | 2002 Aug |
|
| Determination of transport in the Caco-2 cell assay of compounds varying in lipophilicity using LC-MS: enhanced transport of Leu-enkephalin analogues. | 2002 Aug |
|
| Shorter courses of parenteral antibiotic therapy do not appear to influence response rates for children with acute hematogenous osteomyelitis: a systematic review. | 2002 Aug 14 |
|
| A two-step, one-pot enzymatic synthesis of cephalexin from D-phenylglycine nitrile. | 2002 Aug 5 |
|
| Advantages of using non-isothermal bioreactors for the enzymatic synthesis of antibiotics: the penicillin G acylase as enzyme model. | 2002 Aug 5 |
|
| Solid state 'adsorption' of fine antibiotic powders onto sorbitol: effects of particle size, state of sorbed water and surface free energy characteristics. | 2002 Dec |
|
| Orbital abscess following uncomplicated phacoemulsification cataract surgery. | 2002 Dec |
|
| Clinical significance and epidemiology of NO-1, an unusual bacterium associated with dog and cat bites. | 2002 Feb |
|
| A comparison of the efficacy and safety of mupirocin cream and cephalexin in the treatment of secondarily infected eczema. | 2002 Jan |
|
| [Streptococcus salivarius meningitis after oral trauma by a skewer: a case report]. | 2002 Jan |
|
| Comparison of bidirectional cephalexin transport across MDCK and caco-2 cell monolayers: interactions with peptide transporters. | 2002 Jan |
|
| Antimicrobial sensitivity in enterobacteria from AIDS patients, Zambia. | 2002 Jan |
|
| Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections. | 2002 Jan 15 |
|
| [Pharmacokinetics of cephalexin from two oral formulations in dogs]. | 2002 Jan-Feb |
|
| Outcome of percutaneous nephrostomy for the management of pyonephrosis. | 2002 Jul |
|
| Pharmacokinetics of cephalexin in the horse after intravenous and intramuscular administration of two formulations. | 2002 Jul |
|
| Update on prosthetic joints, dental treatment, and antibiotic prophylaxis. | 2002 Jul |
|
| Staphylococcus aureus: colonizing features and influence of an antibacterial treatment in adults with atopic dermatitis. | 2002 Jul |
|
| Antibacterial activity of oral antibiotics against community-acquired respiratory pathogens from three European countries. | 2002 Jul |
|
| Comparison of several methods used for the determination of cephalosporins. Analysis of cephalexin in pharmaceutical samples. | 2002 Jul 1 |
|
| Febrile urinary tract infection: Escherichia coli susceptibility to oral antimicrobials. | 2002 Mar |
|
| Antibiotic prophylaxis in infants and young children with cystic fibrosis: a randomized controlled trial. | 2002 Mar |
|
| Evaluation of UV-radiation induced singlet oxygen generation potential of selected drugs. | 2002 May |
|
| Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis. | 2002 May 1 |
|
| [Use of antibiotics in general practice and at the Clinic for Infectious Diseases]. | 2002 May-Jun |
|
| [Bacteriologic examination of gallbladder contents]. | 2002 May-Jun |
|
| Influence of a new prophylactic antibiotic therapy on the incidence of liver abscesses after chemoembolization treatment of liver tumors. | 2002 Nov |
|
| Risk of serious skin disorders among users of oral antifungals: a population-based study. | 2002 Nov 28 |
|
| Modelling of the enzymatic kinetically controlled synthesis of cephalexin: influence of diffusion limitation. | 2002 Nov 5 |
|
| Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin. | 2002 Oct 20 |
|
| Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1. | 2002 Sep |
|
| Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions. | 2002 Sep 23 |
|
| Enzyme reaction engineering: effect of methanol on the synthesis of antibiotics catalyzed by immobilized penicillin G acylase under isothermal and non-isothermal conditions. | 2002 Sep-Oct |
|
| Frequency of isolation and antimicrobial susceptibility patterns of Staphylococcus intermedius and Pseudomonas aeruginosa isolates from canine skin and ear samples over a 6-year period (1992-1997). | 2002 Sep-Oct |
Sample Use Guides
Adults — The adult dosage ranges from 1 to 4 g daily in divided doses. The usual adult dose is 250 mg every 6 hours. For the following infections, a dosage of 500 mg may be administered every 12 hours: streptococcal pharyngitis, skin and skin structure infections, and uncomplicated cystitis in patients over 15 years of age. Cystitis therapy should be continued for 7 to 14 days. For more severe infections or those caused by less susceptible organisms, larger doses may be needed. If daily doses of Keflex greater than 4 g are required, parenteral cephalosporins, in appropriate doses, should be considered.
Pediatric Patients — The usual recommended daily dosage for pediatric patients is 25 to 50 mg/kg in divided doses. For streptococcal pharyngitis in patients over 1 year of age and for skin and skin structure infections, the total daily dose may be divided and administered every 12 hours. In severe infections, the dosage may be doubled. In the therapy of otitis media, clinical studies have shown that a dosage of 75 to 100 mg/kg/day in 4 divided doses is required. In the treatment of β-hemolytic streptococcal infections, a therapeutic dosage of Keflex should be administered for at least 10 days.
Route of Administration:
Oral
All strains of group A beta-hemolytic streptococci and Diplococcus pneumoniae were inhibited by 3.1 mug/ml. Of the Staphylococcus aureus strains, 88% were inhibited by 6.3 mug/ml, and 12.5 mug/ml was inhibitory for all S. aureus, 80% of Escherichia coli, 72% of Klebsiella-Aerobacter, and 56% of Proteus mirabilis strains. About 90 to 96% of E. coli, Klebsiella Aerobacter, and P. mirabilis strains were inhibited by 25 mug of cephalexin per ml. Pseudomonas and indole-positive Proteus strains proved to be quite resistant to cephalexin.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
MT4YEC9GUQ
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| Record Status |
Validated (UNII)
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| Record Version |
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ACTIVE MOIETY |