CEFADROXIL SODIUM

First approved in 1978

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H16N3O5S.Na
Molecular Weight	385.37
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[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=GQOVFIUWRATNJC-CYJZLJNKSA-M

InChI=1S/C16H17N3O5S.Na/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);/q;+1/p-1/t10-,11-,15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H16N3O5S
Molecular Weight	362.38
Charge	-1
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3542485 | https://www.ncbi.nlm.nih.gov/pubmed/848939

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Solute carrier family 15 member 2 8 Target ID: CHEMBL1743125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107517 \| https://www.ncbi.nlm.nih.gov/pubmed/14600253 \| https://www.ncbi.nlm.nih.gov/pubmed/27836942	Substrate 661
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/050512s046,050527s022,050528s020lbl.pdf	Curative		Approved 8429	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 1978

C_max

Value	Dose	Co-administered	Analyte	Population
17.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073267/	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

Value	Dose	Co-administered	Analyte	Population
50.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073267/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073267/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803251	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: https://pubmed.ncbi.nlm.nih.gov/3803251	Disc. AE: Diarrhoea... AEs leading to discontinuation/dose reduction: Diarrhoea (severe, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3803251
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: https://pubmed.ncbi.nlm.nih.gov/8295811/	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: https://pubmed.ncbi.nlm.nih.gov/8295811/	Other AEs: Vomiting... Other AEs: Vomiting (9 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/8295811/

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803250	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: https://pubmed.ncbi.nlm.nih.gov/3803250
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: https://pubmed.ncbi.nlm.nih.gov/3803251	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: https://pubmed.ncbi.nlm.nih.gov/3803251
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: https://pubmed.ncbi.nlm.nih.gov/8295811/	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: https://pubmed.ncbi.nlm.nih.gov/8295811/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	PEPT2 32 PEPT1 49 OATP transporters 4 MRP transporters 10 MRP3 50 MRP4 77 OAT1 326 OAT3 339

Drug as victim

Target	Modality	Activity
MRP transporters 10	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25414790/	yes
MRP3 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22166395/	yes
MRP4 77	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22166395/	yes
OAT1 326	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25266751/	yes
OAT3 339	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25266751/	yes
OATP transporters 4	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25414790/	yes
PEPT1 49	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16627568/; https://pubmed.ncbi.nlm.nih.gov/31254495/	yes
PEPT2 32	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16041713/; https://pubmed.ncbi.nlm.nih.gov/31254495/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1173	http://www.3bsc.com/index/pro_info.php?id=54889
3B Scientific (Wuhan) Corp	3B2-1711	http://www.3bsc.com/index/pro_info.php?id=56204
AA Blocks	AA006U4S	https://www.aablocks.com/goods/Goods/detail?id=AA006U4S
AHH Chemical co.,ltd	MT-49060	http://www.ahhchemical.com/product/MT-49060.html
AHH Chemical co.,ltd	MT-49061	http://www.ahhchemical.com/product/MT-49061.html
AK Scientific, Inc. (AKSCI)	67486	http://www.aksci.com/item_detail.php?cat=67486
Aaron Chemicals	AR006UWK	http://www.aaronchem.com/50370-12-2
AbMole Bioscience	M5484	http://www.abmole.com/products/cefadroxil.html
Achemtek	0104-005499	http://www.achemtek.com/66592-87-8
Acros Organics	AC459470010	https://www.fishersci.com/shop/products/cefadroxil-95-105-acros-organics-1/AC459470010
Acros Organics	AC459470050	https://www.fishersci.com/shop/products/cefadroxil-95-105-acros-organics/AC459470050
Alfa Chemistry	AP50370122	https://reagents.alfa-chemistry.com/product/cefadroxil-cas-50370-12-2-12115.html
Alsachim	5021	http://www.alsachim.com/product-C6421-glo.bal-view.html
Ambeed	A277245	https://www.ambeed.com/products/50370-12-2.html
Aurora Fine Chemicals LLC	A13.139.707	http://online.aurorafinechemicals.com/info?ID=A13.139.707
BLD Pharm	BD120240	http://www.bldpharm.com/products/50370-12-2.html
BenchChem	B523057	https://www.benchchem.com/product/b523057
BioSynth	C-2462	https://www.biosynth.com/products/biochemistry/culture-media-additives/products/C-2462.html
CSNpharm	CSN10561	https://www.csnpharm.com/products/cefadroxil.html
Chem Scene	CS-4696	http://www.chemscene.com/50370-12-2.html
ChemMol	99098543	http://www.chemmol.com/chemmol/99098543.html
Chemspace	CSSB00020619464	https://chem-space.com/CSSB00020619464
Clearsynth	CS-O-06205	https://www.clearsynth.com/en/CSO06205.html
Combi-Blocks	QB-1083	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-1083
DC Chemicals	DC31585	http://www.dcchemicals.com//product_show-Cefadroxil.html
Glentham Life Sciences	GP4600	http://www.glentham.com/products/product/GP4600/
LGC Standards	DRE-C11063000	https://www.lgcstandards.com/US/en/p/DRE-C11063000
Lab Network	LN00831348	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00831348
MedChem Express	HY-B1190	https://www.medchemexpress.com/Cefadroxil.html
MuseChem	I003787	https://www.musechem.com/product/I003787.html
MuseChem	R007564	https://www.musechem.com/product/R007564.html
OChem	20460	http://www.ocheminc.com/index.php?act=psearch&pid=592C878
Parchem	86915	https://www.parchem.com/chemical-supplier-distributor/Cefadroxil--Anhydrous-086915.aspx
Sigma-Aldrich	C7020_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c7020?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S523057	http://www.smolecule.com/products/s523057
THE BioTek	bt-263288	https://www.thebiotek.com/product/inhibitors/bt-263288
abcr GmbH	AB509151	http://www.abcr.com/shop/en/AB509151
eNovation Chemicals	D674197	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674197
mcule	MCULE-6475996520	https://mcule.com/MCULE-6475996520/

PubMed

Title	Date	PubMed
The importance of Bi-Digital O-Ring Test in the treatment of multiple hepatic abscesses: a case history.	2003	14998058
Antimicrobial resistance in Escherichia coli in urine samples from children and adults: a 12 year analysis.	2004 Apr	15188976
Meta-analysis of cephalosporin versus penicillin treatment of group A streptococcal tonsillopharyngitis in children.	2004 Apr	15060239
Synthesis, characterization and electronic spectra of cefadroxil complexes of d-block elements.	2004 Aug	15249008
Comparison of trimethoprim-sulfamethoxazole, cephadroxil and cefprozil as prophylaxis for recurrent urinary tract infections in children.	2004 Feb	15078003
Comparative bioavailability of two cefadroxil products using serum and urine data in healthy human volunteers.	2004 Jul	15236630
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	15330985
Physician behaviour for antimicrobial prescribing for paediatric upper respiratory tract infections: a survey in general practice in Trinidad, West Indies.	2004 Jun 14	15196306
Direct visualization of peptide uptake activity in the central nervous system of the rat.	2004 Jun 24	15193750
Molecularly imprinted solid phase extraction-pulsed elution-mass spectrometry for determination of cephalexin and alpha-aminocephalosporin antibiotics in human serum.	2004 Nov 15	15522521
Antimicrobial susceptibility of skin-colonizing S. aureus strains in children with atopic dermatitis.	2004 Oct	15482526
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	15282109
Staphylococcal skin infections in children: rational drug therapy recommendations.	2005	15871629
PEPT2 (Slc15a2)-mediated unidirectional transport of cefadroxil from cerebrospinal fluid into choroid plexus.	2005 Dec	16107517
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.	2005 Jan	15567297
Heterogeneity of the IgE response to allergenic determinants of cefaclor in serum samples from patients with cefaclor-induced anaphylaxis.	2005 Jun	15984605
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	15894465
Presumed pituitary abscess without infectious source treated successfully with antibiotics alone.	2005 Sep	16148624
Functional expression of the peptide transporter PEPT2 in the mammalian enteric nervous system.	2005 Sep 12	16041713
A sensitive assay of amoxicillin in mouse serum and broncho-alveolar lavage fluid by liquid-liquid extraction and reversed-phase HPLC.	2005 Sep 15	15935600
Quantitative structure/activity relationship modelling of pharmacokinetic properties using genetic algorithm-combined partial least squares method.	2006	17062396
Urinary bactericidal activity of oral antibiotics against common urinary tract pathogens in an ex vivo model.	2006	17008781
Determination of cefadroxil by sequential injection with spectrophotometric detector.	2006 Apr	16760604
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	16557318
Medication use for pediatric upper respiratory tract infections.	2006 Aug	16867023
European Surveillance of Antimicrobial Consumption (ESAC): outpatient cephalosporin use in Europe.	2006 Aug	16735416
Choroid plexus epithelial monolayers--a cell culture model from porcine brain.	2006 Dec 21	17184532
Cephalosporins can be prescribed safely for penicillin-allergic patients.	2006 Feb	16451776
Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1.	2006 Jul 1	16627568
Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction.	2006 Jul-Aug	16791833
Chiral separation of cefadroxil by capillary electrochromatography.	2006 Jun 16	16600557
Development of a Health-Related Quality of Life Questionnaire (HRQL) for patients with Extremity Soft Tissue Infections (ESTI).	2006 Oct 11	17034641
Generalizability in two clinical trials of Lyme disease.	2006 Oct 17	17044928
Treatment of lichen sclerosus with antibiotics.	2006 Sep	16961523
Flow injection chemiluminescence determination of cefadroxil using potassium permanganate and formaldehyde system.	2006 Sep 18	16766156
Species distribution and properties of staphylococci from canine dermatitis.	2007 Feb	17126372
Impact of genetic knockout of PEPT2 on cefadroxil pharmacokinetics, renal tubular reabsorption, and brain penetration in mice.	2007 Jul	17452417
Idiopathic granulomatous mastitis masquerading as carcinoma of the breast: a case report and review of the literature.	2007 Jul 27	17662130
Determination of beta-lactam antibiotics in milk using micro-flow chemiluminescence system with on-line solid phase extraction.	2007 Jun 5	17512825
Do physician outcome judgments and judgment biases contribute to inappropriate use of treatments? Study protocol.	2007 Jun 7	17555586
Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes.	2007 Mar	17120020
Symptomatic relapse of group A beta-hemolytic streptococcal tonsillopharyngitis in children.	2007 May	17475987
Hydrates and solid-state reactivity: a survey of beta-lactam antibiotics.	2007 May	17455335
Determination of cefquinome in pig plasma and bronchoalveolar lavage fluid by high-performance liquid chromatography combined with electrospray ionization mass spectrometry.	2007 May	17427999
Human oral drugs absorption is correlated to their in vitro uptake by brush border membrane vesicles.	2007 May 4	17178445
Fluorescence studies of the dehydration of cefadroxil monohydrate.	2007 Oct	17621676
In vitro activity of cefadroxil, cephalexin, cefatrizine and cefpirome in presence of essential and trace elements.	2007 Oct	17604254
DRESS syndrome from cefadroxil confirmed by positive patch test.	2007 Oct	17578496
Multi-objective optimization of an industrial penicillin V bioreactor train using non-dominated sorting genetic algorithm.	2007 Oct 15	17405176
A comparative study of capillary zone electrophoresis and pH-potentiometry for determination of dissociation constants.	2007 Sep 3	17537608

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 `Sat Dec 16 11:09:17 GMT 2023` Edited by `admin` on `Sat Dec 16 11:09:17 GMT 2023`
Record UNII	SSZ6380I0I
Record Status	`Validated (UNII)`
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Name

Type

Language

CEFADROXIL SODIUM

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-, SODIUM SALT (1:1), (6R,7R)-

Systematic Name

English

Code System Code Type Description

DRUG BANK

DBSALT002304