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targets (4) transporters (5)
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Identification
Name Cefadroxil
Accession Number DB01140 (APRD00196)
Type small molecule
Groups approved
Description

Long-acting, broad-spectrum, water-soluble, cephalexin derivative. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • CDX
  • Cefadroxil Monohydrate
  • Cefradroxil
Brand names
  • Baxan
  • Bidocef
  • Cefa-Drops
  • Cefamox
  • Cephos
  • Duracef
  • Kefroxil
  • Oracefal
  • Sedral
  • Sumacef
  • Ultracef
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 66592-87-8
Weight Average: 363.388
Monoisotopic: 363.088891359
Chemical Formula C16H17N3O5S
InChI Key InChIKey=BOEGTKLJZSQCCD-UHFFFAOYSA-N
InChI
InChI=1S/C16H17N3O5S/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)
Plain Text
IUPAC Name
7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
CC1=C(N2C(SC1)C(NC(=O)C(N)C1=CC=C(O)C=C1)C2=O)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Phenethylamines
  • Cephalosporins
Substructures
  • Hydroxy Compounds
  • Acetates
  • Phenols and Derivatives
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Beta Lactams
  • Enamines
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
  • Phenyl Esters
Pharmacology
Indication For the treatment of the following infections (skin, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staphylococci and Streptococcus pyogenes
Pharmacodynamics Cefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.
Mechanism of action Like all beta-lactam antibiotics, cefadroxil binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefadroxil interferes with an autolysin inhibitor.
Absorption Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.
Volume of distribution Not Available
Protein binding Binding rates of cefadroxil were 28.1% by U.F. method
Metabolism
Route of elimination Over 90% of the drug is excreted unchanged in the urine within 24 hours. It crosses the placenta and appears in breast milk.
Half life 1.5 hours
Clearance Not Available
Toxicity Nausea, vomiting, diarrhoea, allergic rashes may occur
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Aurobindo pharma ltd
  • Hikma pharmaceuticals
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lupin ltd
  • Orchid healthcare
  • Purepac pharmaceutical co
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Warner chilcott inc
  • Bristol laboratories inc div bristol myers co
  • Apothecon inc div bristol myers squibb
  • Ranbaxy pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Prices
Unit description Cost Unit
Duricef 1 gm tablet 7.35 USD tablet
Cefadroxil 1 gm tablet 7.14 USD tablet
Patents Not Available
Properties
State solid
Melting point 197oC
Experimental Properties
Property Value Source
water solubility 1110 mg/L PhysProp
logP -0.4 PhysProp
Predicted Properties
Property Value Source
water solubility 3.99e-01 g/l ALOGPS
logP 0.51 ALOGPS
logP -3.84 ChemAxon Molconvert
logS -2.96 ALOGPS
pKa 9.48 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 132.96 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 90.95 ChemAxon Molconvert
polarizability 35.65 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00257 Link_out
KEGG Compound C06878 Link_out
PubChem Compound 2610 Link_out
PubChem Substance 46509128 Link_out
ChemSpider 2511 Link_out
ChEBI 3479 Link_out
ChEMBL 3479 Link_out
Therapeutic Targets Database DAP000446 Link_out
Drug Product Database 2240774 Link_out
RxList http://www.rxlist.com/cgi/generic/cefadrox.htm Link_out
Drugs.com http://www.drugs.com/cdi/cefadroxil.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefadroxil Link_out
ATC Codes
  • J01DB05
AHFS Codes
  • 08:12.06.04
PDB Entries Not Available
FDA label show (334.5 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Food may reduce the digestive problems that sometimes occur.
  • Take without regard to meals.
Targets

1. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

2. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q8DR59 Link_out
Gene: pbpA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

3. Penicillin-binding protein 1b

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q7CRA4 Link_out
Gene: pbp1b Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

4. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M6 Link_out
Gene: penA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed
Transporters

1. Oligopeptide transporter, small intestine isoform

Actions: substrate, inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. Pubmed
  2. Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. Pubmed
  3. Balimane PV, Tamai I, Guo A, Nakanishi T, Kitada H, Leibach FH, Tsuji A, Sinko PJ: Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun. 1998 Sep 18;250(2):246-51. Pubmed
  4. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. Pubmed
  5. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
  6. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  7. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. Pubmed
  8. Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A: The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine. J Pharm Pharmacol. 1997 Aug;49(8):796-801. Pubmed

2. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed

3. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. Pubmed
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. Pubmed
  3. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed

4. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. Pubmed
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  3. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

5. Solute carrier family 22 member 8

Actions: inhibitor

Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

UniProt ID: Q8TCC7 Link_out
Gene: SLC22A8 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. Pubmed
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:08

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.