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Prestwick3_001102

Prestwick3_001102

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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

Prestwick3_001102

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 Formula	C₁₅H₁₄ClN₃O₄S
Molecular Weight	367.8 g/mol
XLogP3	-1.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	367.0393548 g/mol
Monoisotopic Mass	367.0393548 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	606
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	Cefaclor
PubMed Health	Cefaclor (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefaclor 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 Ingredient	Cefaclor
Dosage Form	Tablet, extended release; Capsule; For suspension
Route	Oral
Strength	eq 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 Status	Prescription
Company	Teva; Yung Shin Pharm; Hikma

2 of 2
Drug Name	Cefaclor
PubMed Health	Cefaclor (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefaclor 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 Ingredient	Cefaclor
Dosage Form	Tablet, extended release; Capsule; For suspension
Route	Oral
Strength	eq 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 Status	Prescription
Company	Teva; 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.

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