U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N3O4S
Molecular Weight 347.3906
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALEXIN ANHYDROUS

SMILES

CC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])SC1)N=C([C@@]([H])(c3ccccc3)N)O

InChI

InChIKey=ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
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

HIDE SMILES / InChI
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.

CNS Activity

Curator's Comment:: Cephalexin is brain penetrant and neurotoxic in animals. No human data available.

Originator

Curator's Comment:: # Eli Lilly

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KEFLEX

Approved Use

Cephalexin 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 Date

3.17952E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
18.25 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
31.22 μg × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.12 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cephalexin-related nephropathy.
1975 Nov 10
Current issues in antimicrobial therapy for the treatment of acne.
2001
Recurrent diarrhea associated with enterotoxigenic Clostridium perfringens in 2 dogs.
2001 Apr
Upper respiratory tract infections.
2001 Dec
Mycobacterium abscessus wound infection.
2001 Feb
Modeling of the enzymatic kinetic synthesis of cephalexin--influence of substrate concentration and temperature.
2001 May 5
Introduction of recirculatory analysis into portal and systemic concentration difference method.
2001 Nov
PepT1-mediated epithelial transport of dipeptides and cephalexin is enhanced by luminal leptin in the small intestine.
2001 Nov
ED management of cellulitis: a review of five urban centers.
2001 Nov
Correlation between epithelial cell permeability of cephalexin and expression of intestinal oligopeptide transporter.
2001 Nov
[The use of veterinary drugs during pregnancy of the dog].
2001 Nov 15
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.
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
Infantile pertussis rediscovered in China.
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
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
[Streptococcus salivarius meningitis after oral trauma by a skewer: a case report].
2002 Jan
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections.
2002 Jan 15
Pharmacokinetics of cephalexin in the horse after intravenous and intramuscular administration of two formulations.
2002 Jul
Antibacterial activity of oral antibiotics against community-acquired respiratory pathogens from three European countries.
2002 Jul
Susceptibility change to antibiotics of Staphylococcus aureus strains isolated from skin infections between July 1994 and November 2000.
2002 Jun
Antibiotic prophylaxis in infants and young children with cystic fibrosis: a randomized controlled trial.
2002 Mar
Emergence of new pathogens in CF: the devil we know or the devil we don't know?
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
[Bacteriologic examination of gallbladder contents].
2002 May-Jun
Risk of serious skin disorders among users of oral antifungals: a population-based study.
2002 Nov 28
In vitro permeation of beta-lactam antibiotics across rat jejunum and its correlation with oral bioavailability in humans.
2002 Oct
Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin.
2002 Oct 20
Patents

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
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.
Name Type Language
CEPHALEXIN ANHYDROUS
Common Name English
CEPHALEXIN [HSDB]
Common Name English
NSC-758162
Code English
DURANTEL
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINOPHENYLACETYL)AMINO)-3-METHYL-8-OXO-,(6R-(6.ALPHA.,7.BETA.(R*)))-
Common Name English
UPHALEXIN
Common Name English
FELEXIN
Common Name English
EFALEXIN
Common Name English
KEFLORIDINA
Common Name English
CEFALEXIN [WHO-DD]
Common Name English
TAICELEXIN
Common Name English
(6R,7R)-7-((R)-2-AMINO-2-PHENYLACETAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
CEFALEXIN ANHYDROUS
Common Name English
ORACOCIN
Common Name English
CEFALEXIN [INN]
Common Name English
CEFALEXIN
INN   WHO-DD  
INN  
Official Name English
PYASSAN
Common Name English
BIOCEF
Common Name English
SINTHECILLIN
Common Name English
IWALEXIN
Common Name English
LILLY-66873
Common Name English
S-6437
Common Name English
7-(D-.ALPHA.-AMINO-.ALPHA.-PHENYLACETAMIDO)-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFALEKSIN
Common Name English
CEPHAMASTEN
Common Name English
ANHYDROUS CEPHALEXIN
Common Name English
ALSPORIN
Common Name English
CEPHALEXIN [MI]
Common Name English
CEFADROS
Common Name English
CARNOSPORIN
Common Name English
CEFALEXIN [JAN]
Common Name English
MAMALEXIN
Common Name English
GARASIN
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
WHO-VATC QJ51RD01
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
WHO-ATC J01DB01
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NCI_THESAURUS C357
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
WHO-VATC QJ51DB01
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
WHO-VATC QJ01DB01
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000175488
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
NDF-RT N0000011161
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
Code System Code Type Description
PUBCHEM
27447
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
EVMPD
SUB06165MIG
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
WIKIPEDIA
CEFALEXIN
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
EPA CompTox
15686-71-2
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
NCI_THESAURUS
C76180
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
FDA UNII
5SFF1W6677
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
RXCUI
1299782
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY RxNorm
INN
2400
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
239-773-6
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
DRUG CENTRAL
571
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL1727
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
HSDB
3022
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
DRUG BANK
DB00567
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
CAS
15686-71-2
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY
MERCK INDEX
M3244
Created by admin on Fri Jun 25 21:58:37 UTC 2021 , Edited by admin on Fri Jun 25 21:58:37 UTC 2021
PRIMARY Merck Index