Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H17N3O4S.H2O |
Molecular Weight | 365.404 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(O)=O
InChI
InChIKey=AVGYWQBCYZHHPN-CYJZLJNKSA-N
InChI=1S/C16H17N3O4S.H2O/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);1H2/t10-,11-,15-;/m1./s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4383049
Curator's Comment: # Eli Lilly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
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 Date3.17952E10 |
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 |
---|---|---|
Cephalexin-related nephropathy. | 1975 Nov 10 |
|
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 |
|
Mycobacterium abscessus wound infection. | 2001 Feb |
|
Bioaugmentation and treatment of cephalexin drug-based pharmaceutical effluent in an upflow anaerobic fluidized bed system. | 2001 Feb |
|
Paediatric antibiotic prescribing by general dental practitioners in England. | 2001 Jul |
|
Special feature: picture of the month. | 2001 Jun |
|
Take a 2nd look at your first impression. | 2001 Mar |
|
Verotoxin-producing Escherichia coli--an environment-induced emerging zoonosis in and around Calcutta. | 2001 Mar |
|
Antibiotic prophylaxis for full-face laser resurfacing: is it necessary? | 2001 Mar |
|
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales. | 2001 Mar |
|
Modeling of the enzymatic kinetic synthesis of cephalexin--influence of substrate concentration and temperature. | 2001 May 5 |
|
Consensus statement on management of antenatally detected hydronephrosis. | 2001 Nov |
|
PepT1-mediated epithelial transport of dipeptides and cephalexin is enhanced by luminal leptin in the small intestine. | 2001 Nov |
|
Correlation between epithelial cell permeability of cephalexin and expression of intestinal oligopeptide transporter. | 2001 Nov |
|
Outpatient management of low-velocity gunshot-induced fractures. | 2001 Oct |
|
CF and antistaphylococcal prophylaxis. | 2001 Oct |
|
Determination of cephalexin in oral suspensions by micellar electrokinetic chromatography. | 2002 |
|
The effect of tablet formulation and hardness on in vitro release of cephalexin from Eudragit L100 based extended release tablets. | 2002 Apr |
|
Effect of UV-B radiation on some common antibiotics. | 2002 Apr |
|
Immunoglobulin E binding determinants on beta-lactam drugs. | 2002 Aug |
|
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 |
|
A comparison of the efficacy and safety of mupirocin cream and cephalexin in the treatment of secondarily infected eczema. | 2002 Jan |
|
Comparison of bidirectional cephalexin transport across MDCK and caco-2 cell monolayers: interactions with peptide transporters. | 2002 Jan |
|
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections. | 2002 Jan 15 |
|
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 |
|
Typhoidal focal suppurative lymphatic abscess. | 2002 Jun |
|
Febrile urinary tract infection: Escherichia coli susceptibility to oral antimicrobials. | 2002 Mar |
|
Emergence of new pathogens in CF: the devil we know or the devil we don't know? | 2002 Mar |
|
A role for the common GTP-binding protein in coupling of chromosome replication to cell growth and cell division. | 2002 Mar 29 |
|
Evaluation of the performance of immobilized penicillin G acylase using active-site titration. | 2002 May 20 |
|
Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1. | 2002 Sep |
|
Selective antibiotic use to prevent postoperative wound infection after external dacryocystorhinostomy. | 2002 Sep |
|
Private pharmacies in Hanoi, Vietnam: a randomized trial of a 2-year multi-component intervention on knowledge and stated practice regarding ARI, STD and antibiotic/steroid requests. | 2002 Sep |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4388601
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
by
admin
on
Edited
Wed Jul 05 22:49:49 UTC 2023
by
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on
Wed Jul 05 22:49:49 UTC 2023
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Record UNII |
OBN7UDS42Y
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Record Status |
Validated (UNII)
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LIVERTOX |
NBK548358
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NCI_THESAURUS |
C357
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NDF-RT |
N0000175488
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LIVERTOX |
NBK548666
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CFR |
21 CFR 520.376
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OBN7UDS42Y
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Cephalexin
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DBSALT001841
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SUB01098MIG
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BINDER->LIGAND |
BINDING
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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TRANSPORTER -> SUBSTRATE | |||
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE | |||
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TRANSPORTER -> INHIBITOR |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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RENAL IMPAIRMENT PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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MIC | BIOLOGICAL |
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PATHOGEN: METHICILLIN-RESISTANT STAPHYLOCOCCI, MOST STRAINS OF ENTEROCOCCI, MOST STRAINS OF ENTEROBACTER spp., MORGANELLA MORGANII, AND PROTEUS VULGARIS |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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MIC | BIOLOGICAL |
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PATHOGEN: S. AUREUS (INCLUDING PENILILLINASE-PRODUCING STRAINS), S. PNEUMONIAE, S. PYOGENES, E. COLI, H. INFLUENZAE, K. PNEUMONIAE, M. CATARRHALIS, P. MIRABILIS |
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