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Chemistry

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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

Cefadroxil

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 Formula	C₁₆H₁₇N₃O₅S
Molecular Weight	363.4 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	363.08889182 g/mol
Monoisotopic Mass	363.08889182 g/mol
Topological Polar Surface Area	158 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	629
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Cefadroxil
PubMed Health	Cefadroxil (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefadroxil 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 Ingredient	Cefadroxil/cefadroxil hemihydrate
Dosage Form	Tablet; Capsule; For suspension
Route	Oral
Strength	eq 250mg base/5ml; eq 500mg base; eq 125mg base/5ml; eq 500mg base/5ml; eq 1gm base
Market Status	Prescription
Company	Ranbaxy; Teva Pharms; Aurobindo; Aurobindo Pharma; Lupin; Sandoz; Hikma Pharms; Orchid Hlthcare; Hikma

2 of 2
Drug Name	Cefadroxil
PubMed Health	Cefadroxil (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefadroxil 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 Ingredient	Cefadroxil/cefadroxil hemihydrate
Dosage Form	Tablet; Capsule; For suspension
Route	Oral
Strength	eq 250mg base/5ml; eq 500mg base; eq 125mg base/5ml; eq 500mg base/5ml; eq 1gm base
Market Status	Prescription
Company	Ranbaxy; 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.

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10 Gangwal Chemicals

3 Ideal Cures Pvt Ltd

3 Ingredion Pharma Solutions

21 Kerry

1 Kima Chemical

3 Lonza Capsugel

12 Microlex e.U

2 Nanjing Bold Chemical

2 Nomisma Healthcare

1 Novo Excipients

1 Pharmatrans-Sanaq

5 Pluviaendo

3 Prachin Chemical

1 Qualicaps

16 Roquette

8 Seppic

4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

11 Sigachi Industries

1 The Dow Chemical Company

1 Valens Pharmachem

3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

59 Fillers, Diluents & Binders

34 Thickeners and Stabilizers

27 Direct Compression

27 Coating Systems & Additives

20 Disintegrants & Superdisintegrants

20 Solubilizers

18 Topical

16 Granulation

15 Controlled & Modified Release

15 Lubricants & Glidants

14 Co-Processed Excipients

12 Parenteral

11 Taste Masking

10 Film Formers & Plasticizers

8 Rheology Modifiers