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Cefadroxil

July 24, 2017
Common Name

Cefadroxil Description

Cefadroxil is only found in individuals that have used or taken this drug. It is a long-acting, broad-spectrum, water-soluble, cephalexin derivative.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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI CDXChEBI Cefadroxil anhydrousChEBI CefadroxiloChEBI CefadroxilumChEBI CephadroxilChEBI D-CefadroxilChEBI (6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator Cefadroxil monohydrateHMDB CefradroxilHMDB 4-HydroxycephalexinMeSH Anhydrous, cefadroxilMeSH BL S 578MeSH BL S578MeSH BL-S578MeSH BidocefMeSH 4 HydroxycephalexinMeSH BL-S 578MeSH BLS 578MeSH CephadroxylMeSH DuricefMeSH Monohydrate, cefadroxilMeSH UltracefMeSH

Chemical Formlia

C16H17N3O5S Average Molecliar Weight

363.388 Monoisotopic Molecliar Weight

363.088891359 IUPAC Name

(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Traditional Name

cephadroxil CAS Registry Number

66592-87-8 SMILES

[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O

InChI Identifier

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)/t10-,11-,15-/m1/s1

InChI Key

BOEGTKLJZSQCCD-UEKVPHQBSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Lactams Direct Parent

Cephalosporins Alternative Parents

  • N-acyl-alpha amino acids and derivatives
  • Alpha amino acid amides
  • Phenylacetamides
  • 1-hydroxy-2-unsubstituted benzenoids
  • Aralkylamines
  • 1,3-thiazines
  • Tertiary carboxylic acid amides
  • Secondary carboxylic acid amides
  • Amino acids
  • Azetidines
  • Thiohemiaminal derivatives
  • Monocarboxylic acids and derivatives
  • Dialkylthioethers
  • Carboxylic acids
  • Azacyclic compounds
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds

    • Substituents

  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Meta-thiazine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Hemithioaminal
  • Thioether
  • Azacycle
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxide
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:3479 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point197 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.99e-01 g/LNot Available LogP-0.4Not Available

    Predicted Properties

    Property Value Source Water Solubility0.4 mg/mLALOGPS logP0.51ALOGPS logP-2.4ChemAxon logS-3ALOGPS pKa (Strongest Acidic)3.45ChemAxon pKa (Strongest Basic)7.43ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area132.96 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity90.95 m3·mol-1ChemAxon Polarizability35.86 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01140

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01140

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01140 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    43630 KEGG Compound ID

    C06878 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cefadroxil NuGOwiki Link

    HMDB15271 Metagene Link

    HMDB15271 METLIN ID

    Not Available PubChem Compound

    47965 PDB ID

    Not Available ChEBI ID

    3479

    Product: PNPG

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Transporters

    General function:
    Involved in ion transmembrane transporter activity
    Specific function:
    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
    Gene Name:
    SLC22A5
    Uniprot ID:
    O76082
    Molecular weight:
    62751.1
    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:10636865 ]
    General function:
    Involved in transporter activity
    Specific function:
    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
    Gene Name:
    SLC15A1
    Uniprot ID:
    P46059
    Molecular weight:
    78805.3
    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:7592745 ]
    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:8627565 ]
    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:9753615 ]
    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:10087037 ]
    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:15567297 ]
    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:9374833 ]
    7. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]
    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:9379359 ]
    General function:
    Involved in transporter activity
    Specific function:
    Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
    Gene Name:
    SLC15A2
    Uniprot ID:
    Q16348
    Molecular weight:
    81782.8
    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:7592745 ]
    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:9374833 ]
    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:15567297 ]
    General function:
    Involved in ion transmembrane transporter activity
    Specific function:
    Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3-azido- 3-deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
    Gene Name:
    SLC22A6
    Uniprot ID:
    Q4U2R8
    Molecular weight:
    61815.8
    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:11909604 ]
    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:12005172 ]
    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:10411577 ]

    PMID: 26634247

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