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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.CC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C2=O)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
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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DURICEF
PubMed

PubMed

TitleDatePubMed
The importance of Bi-Digital O-Ring Test in the treatment of multiple hepatic abscesses: a case history.
2003
Non-hospital antimicrobial usage and resistance in community-acquired Escherichia coli urinary tract infection.
2003 Dec
Enhanced intestinal absorption of drugs by activation of peptide transporter PEPT1 using proton-releasing polymer.
2003 Nov
Prevalence and antimicrobial susceptibility of pathogens in uncomplicated cystitis in Europe. The ECO.SENS study.
2003 Oct
Comparison of azithromycin and cefadroxil for the treatment of uncomplicated skin and skin structure infections.
2003 Sep
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
Mechanisms of cefadroxil uptake in the choroid plexus: studies in wild-type and PEPT2 knockout mice.
2004 Feb
Penicillin acylase-catalyzed synthesis of beta-lactam antibiotics in highly condensed aqueous systems: beneficial impact of kinetic substrate supersaturation.
2004 Feb 5
Thiolated chitosans: development and in vitro evaluation of a mucoadhesive, permeation enhancing oral drug delivery system.
2004 Jan 8
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
Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes.
2007 Mar
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
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:46 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:46 UTC 2019
Record UNII
280111G160
Record Status Validated (UNII)
Record Version
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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
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
CEFADROXIL [USP]
Common Name English
DURACEF
Brand Name English
CEFADROXIL MONOHYDRATE [WHO-DD]
Common Name English
CEFADROXIL [USP-RS]
Common Name English
MJF 11567-3
Code English
CEFADROXIL MONOHYDRATE
EP   MI   VANDF   WHO-DD  
Common Name English
DURICEF
Brand Name English
CEFADROXIL [USAN]
Common Name English
CEFADROXIL MONOHYDRATE [EP]
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 Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
WHO-VATC QJ01DB05
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
CFR 21 CFR 520.314
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
NDF-RT N0000175488
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
LIVERTOX 159
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
WHO-ATC J01DB05
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
Code System Code Type Description
RXCUI
204175
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
NCI_THESAURUS
C28912
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
MESH
D002434
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
MERCK INDEX
M3185
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY Merck Index
RXCUI
407888
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
ALTERNATIVE
WIKIPEDIA
Cefadroxil
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
ChEMBL
CHEMBL1644
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
CAS
66592-87-8
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
EVMPD
SUB13272MIG
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
DRUG BANK
DB01140
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
PUBCHEM
47964
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
RXCUI
2177
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
ALTERNATIVE
IUPHAR
4831
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
calculated on the anhydrous basis
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC