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

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
Flow-injection spectrophotometric determination of certain cephalosporins based on the formation of dyes.	2001 Aug	11601646
Campylobacter, Salmonella, Shigella and Escherichia coli in live and dressed poultry from metropolitan accra.	2001 Dec 4	11764888
In-vitro release kinetics of cefadroxil-loaded sodium alginate interpenetrating network beads.	2001 Mar	11226819
[The use of veterinary drugs during pregnancy of the dog].	2001 Nov 15	11758478
[Effect of subinhibitory levels of selected antibiotics on susceptibility of Staphylococcus aureus strains to phagocytosis and killing by rabbit granulocytes].	2002	12650052
[Acute vesicular eruption over the trunk].	2002 Dec	12433356
Distribution and function of the peptide transporter PEPT2 in normal and cystic fibrosis human lung.	2002 Jan	11809991
Antibacterial activity of oral antibiotics against community-acquired respiratory pathogens from three European countries.	2002 Jul	12077154
Effect of co-administration of piperine on pharmacokinetics of beta-lactam antibiotics in rats.	2002 Mar	12635696
PepT1 mRNA expression is induced by starvation and its level correlates with absorptive transport of cefadroxil longitudinally in the rat intestine.	2002 Oct	12425457
Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1.	2002 Sep	12356285
Linezolid: in infants and children with severe Gram-positive infections.	2003	12765493
In-vitro and in-vivo antibacterial activity evaluation of a polyurethane matrix.	2003 Apr	12803779
Delta-aminolevulinic acid transport in cancer cells of the human extrahepatic biliary duct.	2003 Apr	12649372
Delivery of peptide drugs to the brain by adenovirus-mediated heterologous expression of human oligopeptide transporter at the blood-brain barrier.	2003 Apr	12649351
Efficacy of cephalexin two vs. three times daily vs. cefadroxil once daily for streptococcal tonsillopharyngitis.	2003 Jul-Aug	12921453
Derivative spectrophotometry in the analysis of mixtures of cefotaxime sodium and cefadroxil monohydrate.	2003 Jun 1	12763535
Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics.	2003 Mar 28	12650826
Rapid and sensitive high-performance liquid chromatographic determination of four cephalosporin antibiotics in pharmaceuticals and body fluids.	2003 May 5	12668080
HPLC determination of amoxicillin comparative bioavailability in healthy volunteers after a single dose administration.	2003 May-Aug	12935434
Prevalence and antimicrobial susceptibility of pathogens in uncomplicated cystitis in Europe. The ECO.SENS study.	2003 Oct	14527771
Linezolid for the treatment of methicillin-resistant Staphylococcus aureus infections in children.	2003 Sep	14520144
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
Direct visualization of peptide uptake activity in the central nervous system of the rat.	2004 Jun 24	15193750
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
Quantitative structure/activity relationship modelling of pharmacokinetic properties using genetic algorithm-combined partial least squares method.	2006	17062396
Choroid plexus epithelial monolayers--a cell culture model from porcine brain.	2006 Dec 21	17184532
Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1.	2006 Jul 1	16627568
Chiral separation of cefadroxil by capillary electrochromatography.	2006 Jun 16	16600557
Generalizability in two clinical trials of Lyme disease.	2006 Oct 17	17044928
Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes.	2007 Mar	17120020
Hydrates and solid-state reactivity: a survey of beta-lactam antibiotics.	2007 May	17455335
DRESS syndrome from cefadroxil confirmed by positive patch test.	2007 Oct	17578496

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 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