CEFADROXIL

First approved in 1978

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 Search

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

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 656
Bacterial penicillin-binding protein 232 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8228

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 232 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/050512s046,050527s022,050528s020lbl.pdf	Curative		Approved 8360	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

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 48 OATP transporters 4 MRP transporters 10 MRP3 50 MRP4 75 OAT1 320 OAT3 333

Drug as victim

Target	Modality	Activity
MRP transporters 10	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25414790/	yes
MRP3 50	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/22166395/	yes
MRP4 75	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/22166395/	yes
OAT1 320	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25266751/	yes
OAT3 333	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25266751/	yes
OATP transporters 4	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25414790/	yes
PEPT1 48	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16627568/; https://pubmed.ncbi.nlm.nih.gov/31254495/	yes
PEPT2 32	substrate 3326 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

Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
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
The fecal microflora of 1-3-month-old infants during treatment with eight oral antibiotics.	2002 Jun	12120942
Intestinal transport of cefuroxime axetil in rats: absorption and hydrolysis processes.	2002 Mar 2	11839441
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
The importance of Bi-Digital O-Ring Test in the treatment of multiple hepatic abscesses: a case history.	2003	14998058
Unusual cause of infective discitis in an adolescent.	2003 Apr	12743347
Linezolid versus cefadroxil in the treatment of skin and skin structure infections in children.	2003 Apr	12690270
Non-hospital antimicrobial usage and resistance in community-acquired Escherichia coli urinary tract infection.	2003 Dec	14613955
An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO.SENS Project.	2003 Jan	12493789
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
Prevalence and antimicrobial susceptibility of pathogens in uncomplicated cystitis in Europe. The ECO.SENS study.	2003 Oct	14527771
Meta-analysis of cephalosporin versus penicillin treatment of group A streptococcal tonsillopharyngitis in children.	2004 Apr	15060239
Comparison of trimethoprim-sulfamethoxazole, cephadroxil and cefprozil as prophylaxis for recurrent urinary tract infections in children.	2004 Feb	15078003
Thiolated chitosans: development and in vitro evaluation of a mucoadhesive, permeation enhancing oral drug delivery system.	2004 Jan 8	14684281
Antimicrobial susceptibility of skin-colonizing S. aureus strains in children with atopic dermatitis.	2004 Oct	15482526
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
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
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
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
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
Chiral separation of cefadroxil by capillary electrochromatography.	2006 Jun 16	16600557
Generalizability in two clinical trials of Lyme disease.	2006 Oct 17	17044928
Species distribution and properties of staphylococci from canine dermatitis.	2007 Feb	17126372
Symptomatic relapse of group A beta-hemolytic streptococcal tonsillopharyngitis in children.	2007 May	17475987
Multi-objective optimization of an industrial penicillin V bioreactor train using non-dominated sorting genetic algorithm.	2007 Oct 15	17405176

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

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Name

Type

Language

CEFADROXIL

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

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