Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H27N3O6S.ClH |
Molecular Weight | 497.992 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)OCOC(=O)C(C)(C)C
InChI
InChIKey=SGRIOOASEBLTKK-ATBNALFTSA-N
InChI=1S/C22H27N3O6S.ClH/c1-12-10-32-19-15(24-17(26)14(23)13-8-6-5-7-9-13)18(27)25(19)16(12)20(28)30-11-31-21(29)22(2,3)4;/h5-9,14-15,19H,10-11,23H2,1-4H3,(H,24,26);1H/t14-,15-,19-;/m1./s1
Molecular Formula | C22H27N3O6S |
Molecular Weight | 461.531 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
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
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 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 |
|
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England. | 2001 |
|
Cephalexin tolerated despite delayed aminopenicillin reactions. | 2001 Aug |
|
The pseudomonas hot-foot syndrome. | 2001 Aug 2 |
|
Drug resistant Haemophilus influenzae from respiratory tract infection in a tertiary care hospital in north India. | 2001 Jan-Mar |
|
A rare case of primary group A streptococcal peritonitis. | 2001 Jul |
|
Artificial skin for closure and healing of wounds created by skin cancer excisions. | 2001 Jul |
|
Spectrophotometric determination of selected cephalosporins in drug formulations using flow injection analysis. | 2001 Jul |
|
Antibiotic prophylaxis for full-face laser resurfacing: is it necessary? | 2001 Mar |
|
Mutations in DnaA protein suppress the growth arrest of acidic phospholipid-deficient Escherichia coli cells. | 2001 Mar 1 |
|
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. | 2001 May |
|
[The use of veterinary drugs during pregnancy of the dog]. | 2001 Nov 15 |
|
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 |
|
[Effect of peptide antibacterial factor and changes in Staphylococcus susceptibility to antibiotics]. | 2002 |
|
Cefdinir: an advanced-generation, broad-spectrum oral cephalosporin. | 2002 Apr |
|
Effect of UV-B radiation on some common antibiotics. | 2002 Apr |
|
Prophylactic antibiotics in cirrhotics with upper gastrointestinal hemorrhage: a prospective, controlled trial. | 2002 Aug |
|
Immunoglobulin E binding determinants on beta-lactam drugs. | 2002 Aug |
|
A two-step, one-pot enzymatic synthesis of cephalexin from D-phenylglycine nitrile. | 2002 Aug 5 |
|
[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 |
|
[Pharmacokinetics of cephalexin from two oral formulations in dogs]. | 2002 Jan-Feb |
|
Outcome of percutaneous nephrostomy for the management of pyonephrosis. | 2002 Jul |
|
Update on prosthetic joints, dental treatment, and antibiotic prophylaxis. | 2002 Jul |
|
Emergence of new pathogens in CF: the devil we know or the devil we don't know? | 2002 Mar |
|
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 |
|
In vitro and in situ evidence for the contribution of Labrasol and Gelucire 44/14 on transport of cephalexin and cefoperazone by rat intestine. | 2002 Nov |
|
Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin. | 2002 Oct 20 |
|
Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions. | 2002 Sep 23 |
|
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
Sat Dec 16 09:53:48 GMT 2023
by
admin
on
Sat Dec 16 09:53:48 GMT 2023
|
Record UNII |
H2Q6O02R95
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000183498
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY | |||
|
DTXSID20182079
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY | |||
|
H2Q6O02R95
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY | |||
|
248-622-3
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY | |||
|
27726-31-4
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY | |||
|
m8897
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY | Merck Index | ||
|
21126684
Created by
admin on Sat Dec 16 09:53:48 GMT 2023 , Edited by admin on Sat Dec 16 09:53:48 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |