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    Cefadroxil

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 50370-12-2, Cefadroxil anhydrous, Cephadroxil, Cefadroxilo, Cefadroxilum, D-cefadroxil
    Molecular Formula
    C16H17N3O5S
    Molecular Weight
    363.4  g/mol
    InChI Key
    BOEGTKLJZSQCCD-UEKVPHQBSA-N
    FDA UNII
    Q525PA8JJB
    Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.
    Cefadroxil anhydrous is a Cephalosporin Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (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 acid
    2.1.2 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)/t10-,11-,15-/m1/s1
    2.1.3 InChI Key
    BOEGTKLJZSQCCD-UEKVPHQBSA-N
    2.1.4 Canonical SMILES
    CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O
    2.1.5 Isomeric SMILES
    CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    Q525PA8JJB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4 Hydroxycephalexin

    2. 4-hydroxycephalexin

    3. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r-(6alpha,7beta(r*)))-

    4. Bidocef

    5. Bl S 578

    6. Bl S578

    7. Bl-s 578

    8. Bl-s578

    9. Bls 578

    10. Bls578

    11. Cefadroxil Anhydrous

    12. Cefadroxil Monohydrate

    13. Cephadroxyl

    14. Duricef

    15. S 578

    16. S-578

    17. S578

    18. Ultracef

    2.3.2 Depositor-Supplied Synonyms

    1. 50370-12-2

    2. Cefadroxil Anhydrous

    3. Cephadroxil

    4. Cefadroxilo

    5. Cefadroxilum

    6. D-cefadroxil

    7. Cefadroxil [inn]

    8. Bl-s578

    9. Anhydrous Cefadroxil

    10. Chebi:3479

    11. (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 Acid

    12. (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 Acid

    13. Bl-s 578

    14. Cdx

    15. Q525pa8jjb

    16. Duracef

    17. Nsc-756664

    18. Dsstox_cid_2749

    19. Dsstox_rid_76714

    20. Dsstox_gsid_22749

    21. Mjf-11567-3

    22. (6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    23. Cefadroxil (as Monohydrate)

    24. Cefadroxilum [inn-latin]

    25. Cefadroxilo [inn-spanish]

    26. (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

    27. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r,7r)-

    28. Sumacef (tn)

    29. Cefadroxil/cefadroxil Hemihydrate

    30. S 578

    31. S-578

    32. Unii-q525pa8jjb

    33. Cefradroxil

    34. Cefadrops

    35. Ncgc00016858-01

    36. (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 Acid

    37. Einecs 256-555-6

    38. Cas-50370-12-2

    39. Cefadroxil, Anhydrous

    40. Cefadroxil (jp17)

    41. Spectrum_000104

    42. Cefadroxil [mi]

    43. Cefadroxil [jan]

    44. (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    45. Prestwick0_000434

    46. Prestwick1_000434

    47. Prestwick2_000434

    48. Prestwick3_000434

    49. Spectrum2_000087

    50. Spectrum4_000266

    51. Spectrum5_000663

    52. Epitope Id:117131

    53. Cefadroxil [who-dd]

    54. Chembl1644

    55. Bspbio_000448

    56. Kbiogr_000732

    57. Kbioss_000544

    58. (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

    59. Mls002207219

    60. Divk1c_000409

    61. Schembl151320

    62. Spbio_000014

    63. Spbio_002387

    64. Cefadroxil, Analytical Standard

    65. Bpbio1_000494

    66. Gtpl4831

    67. Dtxsid8022749

    68. Hms501e11

    69. Kbio1_000409

    70. Kbio2_000544

    71. Kbio2_003112

    72. Kbio2_005680

    73. Ninds_000409

    74. Hms1569g10

    75. Hms2096g10

    76. Hms3713g10

    77. Pharmakon1600-01500163

    78. 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-, (6r,7r)-

    79. Hy-b1190

    80. Zinc3830391

    81. Tox21_110651

    82. Bbl033696

    83. Bdbm50350467

    84. Mfcd00865091

    85. Nsc756664

    86. Stk801939

    87. Akos005622555

    88. Tox21_110651_1

    89. Ccg-220434

    90. Cs-4696

    91. Db01140

    92. Idi1_000409

    93. Ncgc00179556-01

    94. Ncgc00179556-03

    95. As-11655

    96. Smr001306770

    97. Cefprozil Impurity B [ep Impurity]

    98. Sbi-0051305.p003

    99. Ab00513838

    100. Cefprozil E Impurity B [ep Impurity]

    101. C-2462

    102. C06878

    103. D00257

    104. D81830

    105. 592c878

    106. Q2319020

    107. Cefprozil Monohydrate Impurity B [ep Impurity]

    108. Cefadroxil Monohydrate, Antibiotic For Culture Media Use Only

    109. (7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    110. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r-(6-alpha,7-beta(r*)))-

    111. 7beta-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-3,4-didehydrocepham-4-carboxylic Acid

    2.4 Create Date
    2005-07-11
    3 Chemical and Physical Properties
    Molecular Weight 363.4 g/mol
    Molecular Formula C16H17N3O5S
    XLogP3-2.1
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass363.08889182 g/mol
    Monoisotopic Mass363.08889182 g/mol
    Topological Polar Surface Area158 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity629
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameCefadroxil
    PubMed HealthCefadroxil (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCefadroxil monohydrate, USP is a semisynthetic cephalosporin antibiotic intended for oral administration. It is a white to yellowish-white crystalline powder. It is soluble in water and it is acid-stable. It is chemically designated as 5-Thia-1- azab...
    Active IngredientCefadroxil/cefadroxil hemihydrate
    Dosage FormTablet; Capsule; For suspension
    RouteOral
    Strengtheq 250mg base/5ml; eq 500mg base; eq 125mg base/5ml; eq 500mg base/5ml; eq 1gm base
    Market StatusPrescription
    CompanyRanbaxy; Teva Pharms; Aurobindo; Aurobindo Pharma; Lupin; Sandoz; Hikma Pharms; Orchid Hlthcare; Hikma

    2 of 2  
    Drug NameCefadroxil
    PubMed HealthCefadroxil (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCefadroxil monohydrate, USP is a semisynthetic cephalosporin antibiotic intended for oral administration. It is a white to yellowish-white crystalline powder. It is soluble in water and it is acid-stable. It is chemically designated as 5-Thia-1- azab...
    Active IngredientCefadroxil/cefadroxil hemihydrate
    Dosage FormTablet; Capsule; For suspension
    RouteOral
    Strengtheq 250mg base/5ml; eq 500mg base; eq 125mg base/5ml; eq 500mg base/5ml; eq 1gm base
    Market StatusPrescription
    CompanyRanbaxy; Teva Pharms; Aurobindo; Aurobindo Pharma; Lupin; Sandoz; Hikma Pharms; Orchid Hlthcare; Hikma

    4.2 Drug 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

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CEFADROXIL ANHYDROUS
    5.3.2 FDA UNII
    Q525PA8JJB
    5.3.3 Pharmacological Classes
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
    5.4 ATC Code

    J01DB05

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DB - First-generation cephalosporins

    J01DB05 - Cefadroxil

    5.5 Absorption, Distribution and Excretion

    Absorption

    Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.

    Route of Elimination

    Over 90% of the drug is excreted unchanged in the urine within 24 hours. Cefadroxil was detected in the placenta and breast milk.

    5.6 Biological Half-Life

    1.5 hours

    5.7 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.