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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N3O5S
Molecular Weight 363.39
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFADROXIL ANHYDROUS

SMILES

CC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])SC1)N=C([C@@]([H])(c3ccc(cc3)O)N)O

InChI

InChIKey=BOEGTKLJZSQCCD-UEKVPHQBSA-N
InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1

HIDE SMILES / InChI
Cefadroxil is a new semisynthetic cephalosporin with a broad antibacterial spectrum and a high chemotherapeutic potential when administered orally. Many studies have established the efficacy of the administration of once- or twice-daily cefadroxil in the management of infections in the respiratory tract, urinary tract, skin and soft tissues, and bones and joints.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DURICEF

Approved Use

Cefadroxil is indicated for the treatment of patients with infection caused by susceptible strains of the designated organisms in the following diseases: Urinary tract infections caused by E. coli, P. mirabilis, and Klebsiella species. Skin and skin structure infections caused by staphylococci and/or streptococci. Pharyngitis and/or tonsillitis caused by Streptococcus pyogenes (Group A beta-hemolytic streptococci).

Launch Date

2.56521601E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
17.9 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFADROXIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
50.8 μg × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFADROXIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.2 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFADROXIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Other AEs: Rash, Itching...
Other AEs:
Rash (1.5%)
Itching (1.5%)
Pruritus (1.5%)
Nausea (7.5%)
Vomiting (7.5%)
Diarrhoea (7.5%)
Sources:
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 366
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 366
Sources:
Disc. AE: Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Diarrhoea (severe, 2 patients)
Sources:
15 mg/kg 2 times / day steady, oral
Dose: 15 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 15 mg/kg, 2 times / day
Sources:
unhealthy, 6 months - 12 years
n = 113
Health Status: unhealthy
Condition: skin infections
Age Group: 6 months - 12 years
Sex: M+F
Population Size: 113
Sources:
Other AEs: Vomiting...
Other AEs:
Vomiting (9 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Itching 1.5%
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Pruritus 1.5%
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Rash 1.5%
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Diarrhoea 7.5%
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Nausea 7.5%
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Vomiting 7.5%
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 395
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 395
Sources:
Diarrhoea severe, 2 patients
Disc. AE
50 mg/kg 2 times / day steady, oral (max)
Dose: 50 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 2 times / day
Sources:
unhealthy, 2 days -15 years
n = 366
Health Status: unhealthy
Condition: infections
Age Group: 2 days -15 years
Sex: M+F
Population Size: 366
Sources:
Vomiting 9 patients
15 mg/kg 2 times / day steady, oral
Dose: 15 mg/kg, 2 times / day
Route: oral
Route: steady
Dose: 15 mg/kg, 2 times / day
Sources:
unhealthy, 6 months - 12 years
n = 113
Health Status: unhealthy
Condition: skin infections
Age Group: 6 months - 12 years
Sex: M+F
Population Size: 113
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The importance of Bi-Digital O-Ring Test in the treatment of multiple hepatic abscesses: a case history.
2003
Antimicrobial resistance in Escherichia coli in urine samples from children and adults: a 12 year analysis.
2004 Apr
Meta-analysis of cephalosporin versus penicillin treatment of group A streptococcal tonsillopharyngitis in children.
2004 Apr
Synthesis, characterization and electronic spectra of cefadroxil complexes of d-block elements.
2004 Aug
Comparison of trimethoprim-sulfamethoxazole, cephadroxil and cefprozil as prophylaxis for recurrent urinary tract infections in children.
2004 Feb
Comparative bioavailability of two cefadroxil products using serum and urine data in healthy human volunteers.
2004 Jul
Minimum inhibitory concentrations for 25 selected antimicrobial agents against Dichelobacter nodosus and Fusobacterium strains isolated from footrot in sheep of Portugal and Spain.
2004 Jun
Physician behaviour for antimicrobial prescribing for paediatric upper respiratory tract infections: a survey in general practice in Trinidad, West Indies.
2004 Jun 14
Direct visualization of peptide uptake activity in the central nervous system of the rat.
2004 Jun 24
Molecularly imprinted solid phase extraction-pulsed elution-mass spectrometry for determination of cephalexin and alpha-aminocephalosporin antibiotics in human serum.
2004 Nov 15
Antimicrobial susceptibility of skin-colonizing S. aureus strains in children with atopic dermatitis.
2004 Oct
The use of a monolithic column to improve the simultaneous determination of four cephalosporin antibiotics in pharmaceuticals and body fluids by HPLC after solid phase extraction--a comparison with a conventional reversed-phase silica-based column.
2004 Sep 25
Staphylococcal skin infections in children: rational drug therapy recommendations.
2005
PEPT2 (Slc15a2)-mediated unidirectional transport of cefadroxil from cerebrospinal fluid into choroid plexus.
2005 Dec
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
2005 Jan
Heterogeneity of the IgE response to allergenic determinants of cefaclor in serum samples from patients with cefaclor-induced anaphylaxis.
2005 Jun
Bactericidal activity of oral beta-lactam antibiotics in plasma and urine versus isogenic Escherichia coli strains producing broad- and extended-spectrum beta-lactamases.
2005 Jun
Presumed pituitary abscess without infectious source treated successfully with antibiotics alone.
2005 Sep
Functional expression of the peptide transporter PEPT2 in the mammalian enteric nervous system.
2005 Sep 12
A sensitive assay of amoxicillin in mouse serum and broncho-alveolar lavage fluid by liquid-liquid extraction and reversed-phase HPLC.
2005 Sep 15
Quantitative structure/activity relationship modelling of pharmacokinetic properties using genetic algorithm-combined partial least squares method.
2006
Urinary bactericidal activity of oral antibiotics against common urinary tract pathogens in an ex vivo model.
2006
Determination of cefadroxil by sequential injection with spectrophotometric detector.
2006 Apr
Positive effect of natural and negatively charged cyclodextrins on the stabilization of penicillins towards beta-lactamase degradation due to inclusion and external guest-host association. An NMR and MS study.
2006 Apr 7
Medication use for pediatric upper respiratory tract infections.
2006 Aug
European Surveillance of Antimicrobial Consumption (ESAC): outpatient cephalosporin use in Europe.
2006 Aug
Choroid plexus epithelial monolayers--a cell culture model from porcine brain.
2006 Dec 21
Cephalosporins can be prescribed safely for penicillin-allergic patients.
2006 Feb
Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1.
2006 Jul 1
Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction.
2006 Jul-Aug
Chiral separation of cefadroxil by capillary electrochromatography.
2006 Jun 16
Development of a Health-Related Quality of Life Questionnaire (HRQL) for patients with Extremity Soft Tissue Infections (ESTI).
2006 Oct 11
Generalizability in two clinical trials of Lyme disease.
2006 Oct 17
Treatment of lichen sclerosus with antibiotics.
2006 Sep
Flow injection chemiluminescence determination of cefadroxil using potassium permanganate and formaldehyde system.
2006 Sep 18
Species distribution and properties of staphylococci from canine dermatitis.
2007 Feb
Impact of genetic knockout of PEPT2 on cefadroxil pharmacokinetics, renal tubular reabsorption, and brain penetration in mice.
2007 Jul
Idiopathic granulomatous mastitis masquerading as carcinoma of the breast: a case report and review of the literature.
2007 Jul 27
Determination of beta-lactam antibiotics in milk using micro-flow chemiluminescence system with on-line solid phase extraction.
2007 Jun 5
Do physician outcome judgments and judgment biases contribute to inappropriate use of treatments? Study protocol.
2007 Jun 7
Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes.
2007 Mar
Symptomatic relapse of group A beta-hemolytic streptococcal tonsillopharyngitis in children.
2007 May
Hydrates and solid-state reactivity: a survey of beta-lactam antibiotics.
2007 May
Determination of cefquinome in pig plasma and bronchoalveolar lavage fluid by high-performance liquid chromatography combined with electrospray ionization mass spectrometry.
2007 May
Human oral drugs absorption is correlated to their in vitro uptake by brush border membrane vesicles.
2007 May 4
Fluorescence studies of the dehydration of cefadroxil monohydrate.
2007 Oct
In vitro activity of cefadroxil, cephalexin, cefatrizine and cefpirome in presence of essential and trace elements.
2007 Oct
DRESS syndrome from cefadroxil confirmed by positive patch test.
2007 Oct
Multi-objective optimization of an industrial penicillin V bioreactor train using non-dominated sorting genetic algorithm.
2007 Oct 15
A comparative study of capillary zone electrophoresis and pH-potentiometry for determination of dissociation constants.
2007 Sep 3
Patents

Sample Use Guides

In Vivo Use Guide
Cefadroxil tablets are acid-stable and may be administered orally without regard to meals. Administration with food may be helpful in diminishing potential gastrointestinal complaints occasionally associated with oral cephalosporin therapy. Adults Urinary Tract Infections For uncomplicated lower urinary tract infections (i.e., cystitis) the usual dosage is 1 or 2 g per day in a single (q.d.) or divided doses (b.i.d.). For all other urinary tract infections the usual dosage is 2 g per day in divided doses (b.i.d.). Skin and Skin Structure Infections For skin and skin structure infections the usual dosage is 1 g per day in single (q.d.) or divided doses (b.i.d.). Pharyngitis and Tonsillitis Treatment of group A beta-hemolytic streptococcal pharyngitis and tonsillitis – 1 g per day in single (q.d.) or divided doses (b.i.d.) for 10 days. Children For urinary tract infections, the recommended daily dosage for children is 30 mg/kg/day in divided doses every 12 hours. For pharyngitis, tonsillitis, and impetigo, the recommended daily dosage for children is 30 mg/kg/day in a single dose or in equally divided doses every 12 hours. For other skin and skin structure infections, the recommended daily dosage is 30 mg/kg/day in equally divided doses every 12 hours. In the treatment of beta-hemolytic streptococcal infections, a therapeutic dosage of Cefadroxil tablets should be administered for at least 10 days.
Route of Administration: Oral
In Vitro Use Guide
Cefadroxil very effectively inhibited a broad spectrum of gram-positive and gram-negative organisms with MIC (minimal inhibitory concentration) values less than 125 ug/ml.
Name Type Language
CEFADROXIL ANHYDROUS
Common Name English
CEFADROXIL [JAN]
Common Name English
CEFADROXIL [WHO-DD]
Common Name English
CEFADROXIL [INN]
Common Name English
(6R,7R)-7-(((2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETYL)AMINO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
CEFADROXIL [MI]
Common Name English
ANHYDROUS CEFADROXIL
Common Name English
CEFPROZIL E SPECIFIED IMPURITY B [EP]
Common Name English
CEFPROZIL IMPURITY B [EP]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETYL)AMINO)-3-METHYL-8-OXO-, (6R,7R)-
Common Name English
CEFPROZIL MONOHYDRATE IMPURITY B [EP]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
WHO-ATC J01DB05
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000175488
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NDF-RT N0000011161
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
NCI_THESAURUS C357
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
Code System Code Type Description
INN
3719
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
MERCK INDEX
M3185
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY Merck Index
EVMPD
SUB121209
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
RXCUI
1545975
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY RxNorm
EVMPD
SUB06164MIG
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
FDA UNII
Q525PA8JJB
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
EPA CompTox
50370-12-2
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
CAS
50370-12-2
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
NCI_THESAURUS
C79562
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
256-555-6
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY
PUBCHEM
47965
Created by admin on Sat Jun 26 15:33:20 UTC 2021 , Edited by admin on Sat Jun 26 15:33:20 UTC 2021
PRIMARY