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    Cefaclor

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    $ API Ref.Price (USD/KG) : 249Xls

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    2D Structure
    Also known as: 53994-73-3, Cephaclor, Ceclor, Cefaclor anhydrous, Cefaclorum, Kefral
    Molecular Formula
    C15H14ClN3O4S
    Molecular Weight
    367.8  g/mol
    InChI Key
    QYIYFLOTGYLRGG-GPCCPHFNSA-N
    FDA UNII
    3Z6FS3IK0K
    Semisynthetic, broad-spectrum antibiotic derivative of CEPHALEXIN.
    Cefaclor 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-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
    2.1.3 InChI Key
    QYIYFLOTGYLRGG-GPCCPHFNSA-N
    2.1.4 Canonical SMILES
    C1C(=C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)Cl
    2.1.5 Isomeric SMILES
    C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    3Z6FS3IK0K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

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

    2. Ceclor

    3. Cefaclor Anhydrous

    4. Cefaclor Monohydrate

    5. Keclor

    6. Lilly 99638

    7. S 6472

    8. S-6472

    9. S6472

    2.3.2 Depositor-Supplied Synonyms

    1. 53994-73-3

    2. Cephaclor

    3. Ceclor

    4. Cefaclor Anhydrous

    5. Cefaclorum

    6. Kefral

    7. Panoral

    8. Raniclor

    9. Cefaclor [inn]

    10. Cefaclor Hydrate

    11. Cefaclorum [inn-latin]

    12. 3-chloro-7-d-(2-phenylglycinamido)-3-cephem-4-carboxylic Acid

    13. 143059-69-2

    14. S 6472

    15. Cefaclor Impurity C

    16. Chebi:3478

    17. Ccl

    18. 3z6fs3ik0k

    19. Mls000069617

    20. (6r,7r)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    21. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2r)-aminophenylacetyl]amino]-3-chloro-8-oxo-, (6r,7r)-

    22. 53994-73-3 (free)

    23. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    24. (6r,7r)-7-{[(2r)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    25. Ncgc00022612-04

    26. Alfacet

    27. Smr000058250

    28. Dsstox_cid_2748

    29. Dsstox_rid_76713

    30. Dsstox_gsid_22748

    31. Dystaclor Mr

    32. L-kefral

    33. Ceclor Cd

    34. Alenfral (tn)

    35. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    36. (6r,7r)-7-[(2r)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    37. Cas-53994-73-3

    38. Unii-3z6fs3ik0k

    39. Cefaclorimpurityc

    40. S-6472

    41. Cefaclor,(s)

    42. (6r,7r)-7-(((2r)-2-amino-2-phenylacetyl)amino)-3-chloro-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    43. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-2-amino-2-phenylacetyl)amino)-3-chloro-8-oxo-, (6r,7r)-

    44. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-, (6r,7r)-

    45. Einecs 258-909-5

    46. Mfcd00151471

    47. Cefaclor (jp17)

    48. Spectrum_001070

    49. Specplus_000947

    50. Cefaclor [jan]

    51. Cefaclor [mi]

    52. Prestwick0_000485

    53. Prestwick0_001102

    54. Prestwick1_000485

    55. Prestwick1_001102

    56. Prestwick2_000485

    57. Prestwick2_001102

    58. Prestwick3_000485

    59. Prestwick3_001102

    60. Spectrum2_001189

    61. Spectrum3_001858

    62. Spectrum4_000093

    63. Spectrum5_001727

    64. Cefaclor [who-dd]

    65. Chembl680

    66. Epitope Id:117133

    67. Schembl33540

    68. Bspbio_000349

    69. Bspbio_001204

    70. Bspbio_003276

    71. Kbiogr_000386

    72. Kbioss_001550

    73. Cid_51039

    74. Mls001424193

    75. Divk1c_007043

    76. Spectrum1500771

    77. Spbio_001237

    78. Spbio_002270

    79. Spbio_003082

    80. Bpbio1_000385

    81. Bpbio1_001326

    82. Dtxsid3022748

    83. Bdbm42131

    84. Kbio1_001987

    85. Kbio2_001550

    86. Kbio2_004118

    87. Kbio2_006686

    88. Kbio3_002777

    89. Bcpp000294

    90. Hms1571m06

    91. Hms1921g22

    92. Hms2052c11

    93. Hms2092k08

    94. Hms2233m13

    95. Pharmakon1600-01500771

    96. (6r,7r)-7-[[(2s)-2-amino-1-oxo-2-phenylethyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    97. Hy-b0198

    98. Zinc3812869

    99. Tox21_110880

    100. Ccg-40264

    101. Nsc757422

    102. Akos024282614

    103. Tox21_110880_1

    104. Bcp9000501

    105. Cefaclor, Analytical Reference Material

    106. Db00833

    107. Nc00354

    108. 7beta-{[(2r)-2-amino-2-phenylacetyl]amino}-3-chloro-3,4-didehydrocepham-4-carboxylic Acid

    109. Ncgc00015260-22

    110. Ncgc00022612-05

    111. Ncgc00022612-06

    112. Ncgc00022612-07

    113. Ncgc00022612-10

    114. Ncgc00022612-11

    115. 7-((2r)-2-amino-2-phenylacetylamino)(7r,7ar)-3-chloro-6-oxo-2h,7h-azetidino[2, 1-b]1,3-thiazine-4-carboxylic Acid

    116. As-74992

    117. Sbi-0051606.p002

    118. Ab00052174

    119. C3478

    120. C-2461

    121. C06877

    122. D00256

    123. Ab00052174_15

    124. Ab00052174_16

    125. Cefaclor, Antibiotic For Culture Media Use Only

    126. A900728

    127. Q415167

    128. Sr-05000001556

    129. Sr-05000001556-1

    130. Brd-k20338176-002-03-5

    131. 7-(d-2-amino-2-phenylacetamido)-3-chloro-3-cephem-4-carboxylic

    132. (6r,7r)-7-((s)-2-amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    133. (6r,7r)-7-[(r)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic Acid

    134. (6r,7r)-7-[[(2r)-2-amino-2-phenyl-acetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    135. (6r,7r)-7-[[(2r)-2-azaniumyl-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    136. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((aminophenylacetyl)amino)-3-chloro-8-oxo-, (6r-(6-alpha,7-beta(r*)))-

    2.4 Create Date
    2005-06-29
    3 Chemical and Physical Properties
    Molecular Weight 367.8 g/mol
    Molecular Formula C15H14ClN3O4S
    XLogP3-1.8
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count4
    Exact Mass367.0393548 g/mol
    Monoisotopic Mass367.0393548 g/mol
    Topological Polar Surface Area138 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity606
    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 NameCefaclor
    PubMed HealthCefaclor (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCefaclor is a semisynthetic cephalosporin antibiotic for oral administration. It is chemically designated as 3-chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylic acid monohydrate. The molecular formula for cefaclor is C15H14ClN3O4SH2O and the...
    Active IngredientCefaclor
    Dosage FormTablet, extended release; Capsule; For suspension
    RouteOral
    Strengtheq 375mg base/5ml; eq 250mg base/5ml; eq 500mg base; eq 187mg base/5ml; eq 250mg base; eq 125mg base/5ml; eq 375mg base
    Market StatusPrescription
    CompanyTeva; Yung Shin Pharm; Hikma

    2 of 2  
    Drug NameCefaclor
    PubMed HealthCefaclor (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCefaclor is a semisynthetic cephalosporin antibiotic for oral administration. It is chemically designated as 3-chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylic acid monohydrate. The molecular formula for cefaclor is C15H14ClN3O4SH2O and the...
    Active IngredientCefaclor
    Dosage FormTablet, extended release; Capsule; For suspension
    RouteOral
    Strengtheq 375mg base/5ml; eq 250mg base/5ml; eq 500mg base; eq 187mg base/5ml; eq 250mg base; eq 125mg base/5ml; eq 375mg base
    Market StatusPrescription
    CompanyTeva; Yung Shin Pharm; Hikma

    4.2 Drug Indication

    For the treatment of certain infections caused by bacteria such as pneumonia and ear, lung, skin, throat, and urinary tract infections.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefaclor is a second generation cephalosporin antibiotic with a spectrum resembling first-generation cephalosporins. In vitro tests demonstrate that the bactericidal action of the cephalosporins results from inhibition of cell-wall synthesis. As indicated by _in vitro_ and _in vivo_ clinical studies, cefaclor was shown to be effective against most strains of Gram positive aerobes - Staphylococci (including coagulase-positive, coagulase-negative, and penicillinase-producing strains), Streptococcus pneumoniae, Streptococcus pyogenes (group A ß-hemolytic streptococci), as well as Gram-negative aerobes - Escherichia coli, Haemophilus influenzae (including ß-lactamase-producing ampicillin-resistant strains), Klebsiella sp, and Proteus mirabilis.

    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
    CEFACLOR ANHYDROUS
    5.3.2 FDA UNII
    3Z6FS3IK0K
    5.3.3 Pharmacological Classes
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DC - Second-generation cephalosporins

    J01DC04 - Cefaclor

    5.5 Absorption, Distribution and Excretion

    Absorption

    Well absorbed after oral administration, independent of food intake.

    Route of Elimination

    Approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours, the greater portion being excreted within the first 2 hours.

    5.6 Metabolism/Metabolites

    No appreciable biotransformation in liver (approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours).

    5.7 Biological Half-Life

    0.6-0.9 hour

    5.8 Mechanism of Action

    Cefaclor, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits 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 cefaclor interferes with an autolysin inhibitor.