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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N3O5S.H2O
Molecular Weight 381.404
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFADROXIL

SMILES

O.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(O)=O

InChI

InChIKey=NBFNMSULHIODTC-CYJZLJNKSA-N
InChI=1S/C16H17N3O5S.H2O/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);1H2/t10-,11-,15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C16H17N3O5S
Molecular Weight 363.388
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Distribution and function of the peptide transporter PEPT2 in normal and cystic fibrosis human lung.
2002 Jan
Antibacterial activity of oral antibiotics against community-acquired respiratory pathogens from three European countries.
2002 Jul
The fecal microflora of 1-3-month-old infants during treatment with eight oral antibiotics.
2002 Jun
Intestinal transport of cefuroxime axetil in rats: absorption and hydrolysis processes.
2002 Mar 2
PepT1 mRNA expression is induced by starvation and its level correlates with absorptive transport of cefadroxil longitudinally in the rat intestine.
2002 Oct
Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1.
2002 Sep
The importance of Bi-Digital O-Ring Test in the treatment of multiple hepatic abscesses: a case history.
2003
Unusual cause of infective discitis in an adolescent.
2003 Apr
Linezolid versus cefadroxil in the treatment of skin and skin structure infections in children.
2003 Apr
Non-hospital antimicrobial usage and resistance in community-acquired Escherichia coli urinary tract infection.
2003 Dec
An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO.SENS Project.
2003 Jan
Efficacy of cephalexin two vs. three times daily vs. cefadroxil once daily for streptococcal tonsillopharyngitis.
2003 Jul-Aug
Derivative spectrophotometry in the analysis of mixtures of cefotaxime sodium and cefadroxil monohydrate.
2003 Jun 1
Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics.
2003 Mar 28
Rapid and sensitive high-performance liquid chromatographic determination of four cephalosporin antibiotics in pharmaceuticals and body fluids.
2003 May 5
Prevalence and antimicrobial susceptibility of pathogens in uncomplicated cystitis in Europe. The ECO.SENS study.
2003 Oct
Meta-analysis of cephalosporin versus penicillin treatment of group A streptococcal tonsillopharyngitis in children.
2004 Apr
Comparison of trimethoprim-sulfamethoxazole, cephadroxil and cefprozil as prophylaxis for recurrent urinary tract infections in children.
2004 Feb
Thiolated chitosans: development and in vitro evaluation of a mucoadhesive, permeation enhancing oral drug delivery system.
2004 Jan 8
Antimicrobial susceptibility of skin-colonizing S. aureus strains in children with atopic dermatitis.
2004 Oct
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
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
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
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
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
Chiral separation of cefadroxil by capillary electrochromatography.
2006 Jun 16
Generalizability in two clinical trials of Lyme disease.
2006 Oct 17
Species distribution and properties of staphylococci from canine dermatitis.
2007 Feb
Symptomatic relapse of group A beta-hemolytic streptococcal tonsillopharyngitis in children.
2007 May
Multi-objective optimization of an industrial penicillin V bioreactor train using non-dominated sorting genetic algorithm.
2007 Oct 15
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:39:25 UTC 2023
Edited
by admin
on Wed Jul 05 22:39:25 UTC 2023
Record UNII
280111G160
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFADROXIL
GREEN BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CEFADROXIL (AS MONOHYDRATE)
Common Name English
(6R,7R)-7-((R)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID MONOHYDRATE
Common Name English
CEFADROXIL [GREEN BOOK]
Common Name English
NSC-756664
Code English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-3-METHYL-8-OXO-, MONOHYDRATE, (6R-(6.ALPHA.,7.BETA.(R*)))
Common Name English
BL-S578
Code English
DURACEF
Brand Name English
CEFADROXIL MONOHYDRATE [EP MONOGRAPH]
Common Name English
CEFADROXIL [USP-RS]
Common Name English
MJF 11567-3
Code English
CEFADROXIL MONOHYDRATE
EP   MI   VANDF   WHO-DD  
Common Name English
Cefadroxil monohydrate [WHO-DD]
Common Name English
DURICEF
Brand Name English
CEFADROXIL [USAN]
Common Name English
CEFADROXIL [USP MONOGRAPH]
Common Name English
CEFADROXIL HYDRATE
Common Name English
CEFADROXIL [VANDF]
Common Name English
CEFADROXIL MONOHYDRATE [MI]
Common Name English
CEFADROXIL MONOHYDRATE [VANDF]
Common Name English
MJF-11567-3
Code English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
WHO-VATC QJ01DB05
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
CFR 21 CFR 520.314
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
LIVERTOX NBK548358
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
NDF-RT N0000175488
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
LIVERTOX NBK548666
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
WHO-ATC J01DB05
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
Code System Code Type Description
RXCUI
204175
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
DRUG CENTRAL
526
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
DAILYMED
280111G160
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
NCI_THESAURUS
C28912
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
MESH
D002434
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
LACTMED
Cefadroxil
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
SMS_ID
100000092290
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
CHEBI
53667
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
MERCK INDEX
M3185
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY Merck Index
RXCUI
407888
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
ALTERNATIVE
WIKIPEDIA
Cefadroxil
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
RS_ITEM_NUM
1097104
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL1644
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
NSC
756664
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID80904597
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
CAS
66592-87-8
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
FDA UNII
280111G160
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
CHEBI
3479
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
EVMPD
SUB13272MIG
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
DRUG BANK
DB01140
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
PUBCHEM
47964
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
RXCUI
2177
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
ALTERNATIVE
IUPHAR
4831
Created by admin on Wed Jul 05 22:39:25 UTC 2023 , Edited by admin on Wed Jul 05 22:39:25 UTC 2023
PRIMARY
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