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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N3O4S.H2O
Molecular Weight 365.4059
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALEXIN

SMILES

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

HIDE SMILES / InChI

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 347.3906
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

31795200000
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
Dose: 40 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg/kg, 3 times / day
Sources:
unhealthy, 1-16 years
Health Status: unhealthy
Age Group: 1-16 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 90 years
Sex: F
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
Dose: 40 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg/kg, 3 times / day
Sources:
unhealthy, 1-16 years
Health Status: unhealthy
Age Group: 1-16 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 90 years
Sex: F
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
Skin and soft tissue infection.
2001 Jul
Effect of cephalexin on the pharmacokinetics of metformin in healthy human volunteers.
2002
Determination of cephalexin in oral suspensions by micellar electrokinetic chromatography.
2002
[Effect of peptide antibacterial factor and changes in Staphylococcus susceptibility to antibiotics].
2002
Moxifloxacin in uncomplicated skin and skin structure infections.
2002
Cefdinir: an advanced-generation, broad-spectrum oral cephalosporin.
2002 Apr
Salmonella mastitis in a child.
2002 Apr
The effect of tablet formulation and hardness on in vitro release of cephalexin from Eudragit L100 based extended release tablets.
2002 Apr
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.
2002 Apr
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
A comparison of the efficacy and safety of mupirocin cream and cephalexin in the treatment of secondarily infected eczema.
2002 Jan
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections.
2002 Jan 15
Sensitivity and resistance of antibiotics in common infection of male and female.
2002 Jan-Mar
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
Susceptibility change to antibiotics of Staphylococcus aureus strains isolated from skin infections between July 1994 and November 2000.
2002 Jun
Typhoidal focal suppurative lymphatic abscess.
2002 Jun
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
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
Evaluation of the performance of immobilized penicillin G acylase using active-site titration.
2002 May 20
[Use of antibiotics in general practice and at the Clinic for Infectious Diseases].
2002 May-Jun
[Bacteriologic examination of gallbladder contents].
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
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
An indirect conductimetric screening method for the detection of antibiotic residues in bovine kidneys.
2002 Sep
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
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
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.
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:52:22 UTC 2021
Edited
by admin
on Fri Jun 25 20:52:22 UTC 2021
Record UNII
OBN7UDS42Y
Record Status Validated (UNII)
Record Version
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Name Type Language
CEPHALEXIN
ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CEFALEXIN MONOHYDRATE
EP   WHO-DD  
Common Name English
66873
Code English
7-(D-.ALPHA.-AMINO-.ALPHA.-PHENYLACETAMIDO)-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID MONOHYDRATE
Common Name English
KEFLEX
Brand Name English
CEPHALEXIN MONOHYDRATE [MI]
Common Name English
CEFANEX
Brand Name English
CEPHALEXIN MONOHYDRATE
MI   VANDF  
Common Name English
CEPHALEXIN [USP-RS]
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 MONOHYDRATE
Systematic Name English
CEPHALEXIN [USAN]
Common Name English
CEPHALEXIN [VANDF]
Common Name English
CEFALEXIN MONOHYDRATE [WHO-DD]
Common Name English
CEFALEXIN MONOHYDRATE [EP MONOGRAPH]
Common Name English
CEPHALEXIN MONOHYDRATE [VANDF]
Common Name English
KEFLET
Brand Name English
CEPHALEXIN [USP MONOGRAPH]
Common Name English
CEPHALEXIN [ORANGE BOOK]
Common Name English
CEFALEXIN MONOHYDRATE [EP]
Common Name English
PANIXINE DISPERDOSE
Brand Name English
LY-66873
Code English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
NDF-RT N0000175488
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
LIVERTOX 177
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
CFR 21 CFR 520.376
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
Code System Code Type Description
IUPHAR
4832
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL1727
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
MESH
D002506
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
CAS
23325-78-2
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
RXCUI
215948
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
PUBCHEM
62921
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
EVMPD
SUB06165MIG
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
RXCUI
2231
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
ALTERNATIVE
MERCK INDEX
M3244
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C356
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
FDA UNII
OBN7UDS42Y
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
LACTMED
Cephalexin
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
DRUG BANK
DBSALT001841
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
USP_CATALOG
1099008
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY USP-RS
EVMPD
SUB01098MIG
Created by admin on Fri Jun 25 20:52:22 UTC 2021 , Edited by admin on Fri Jun 25 20:52:22 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> SUBSTRATE
PARENT -> SALT/SOLVATE
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC RENAL IMPAIRMENT
PHARMACOKINETIC
Tmax PHARMACOKINETIC
MIC BIOLOGICAL PATHOGEN: METHICILLIN-RESISTANT STAPHYLOCOCCI, MOST STRAINS OF ENTEROCOCCI, MOST STRAINS OF ENTEROBACTER spp., MORGANELLA MORGANII, AND PROTEUS VULGARIS

SUSCEPTIBILITY: RESISTANT

Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
MIC BIOLOGICAL PATHOGEN: S. AUREUS (INCLUDING PENILILLINASE-PRODUCING STRAINS), S. PNEUMONIAE, S. PYOGENES, E. COLI, H. INFLUENZAE, K. PNEUMONIAE, M. CATARRHALIS, P. MIRABILIS

SUSCEPTIBILITY: SUSCEPTIBLE