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Chemistry

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Also known as: Cefradine, 38821-53-3, Cephradin, Anspor, Sefril, Velosef

Molecular Formula

C₁₆H₁₉N₃O₄S

Molecular Weight

349.4 g/mol

InChI Key

RDLPVSKMFDYCOR-UEKVPHQBSA-N

FDA UNII

9YA6SX5S4D

A semi-synthetic cephalosporin antibiotic.

Cephradine anhydrous is a Cephalosporin Antibacterial.

1 2D Structure

Cephradine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

2.1.3 InChI Key

RDLPVSKMFDYCOR-UEKVPHQBSA-N

2.1.4 Canonical SMILES

CC1=C(N2C(C(C2=O)NC(=O)C(C3=CCC=CC3)N)SC1)C(=O)O

2.1.5 Isomeric SMILES

CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CCC=CC3)N)SC1)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

9YA6SX5S4D

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anspor

2. Cefradine

3. Cephradine Dihydrate

4. Cephradine, Non Stoichiometric Hydrate

5. Cephradine, Non-stoichiometric Hydrate

6. Dexef

7. Dihydrate, Cephradine

8. Kelsef

9. Maxisporin

10. Nicef

11. Non-stoichiometric Hydrate Cephradine

12. Sefril

13. Septacef

14. Sq 11436

15. Sq-11436

16. Sq11436

17. Velocef

18. Velosef

19. Zeefra G

2.3.2 Depositor-Supplied Synonyms

1. Cefradine

2. 38821-53-3

3. Cephradin

4. Anspor

5. Sefril

6. Velosef

7. Cefradina

8. Cefradinum

9. Eskacef

10. Sq 11436

11. Cefradin

12. Sq-11436

13. (6r,7r)-7-((r)-2-amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

14. Cefradine [inn]

15. Cephradine Anhydrous

16. 7-(d-2-amino-2-(1,4-cyclohexadienyl)acetamide)desacetoxycephalosporanicacid

17. Chebi:3547

18. (6r,7r)-7-[[(2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

19. 9ya6sx5s4d

20. (6r,7r)-7-{[(2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

21. Nsc-756672

22. Ced

23. Cephradine Hydrate

24. Ncgc00183036-01

25. Dsstox_cid_2785

26. Cefradinum [inn-latin]

27. Cephradine [usan:ban]

28. Dsstox_rid_76729

29. Cefradina [inn-spanish]

30. Dsstox_gsid_22785

31. (6r,7r)-7-[(2r)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

32. (7r)-7-[[(2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

33. Cekodin

34. Megacef

35. Velocef

36. Megace F

37. Skf D 39304

38. Cephradine (usp)

39. Velosef (tn)

40. Velosef '125'

41. Velosef '250'

42. Velosef '500'

43. Anspor (tn)

44. Cas-38821-53-3

45. Hsdb 3216

46. Cefradine (jan/inn)

47. Einecs 254-137-8

48. Unii-9ya6sx5s4d

49. Brn 6075388

50. Infexin

51. Cephradine,(s)

52. (6r,7r)-7-(((2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

53. (6r,7r)-7-((r)-2-amino-2-(cyclohexa-1,4-dienyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

54. Mfcd00865048

55. Sk&f D-39304

56. Sk-d-39304

57. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino-1,4-cyclohexadien-1-ylacetyl)amino)-3-methyl-8-oxo-, (6r-(6alpha,7beta(r*)))-

58. 7-(d-2-amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-caboxylic Acid

59. Sq-22022

60. Cefradine Hydrate

61. Cefradine [jan]

62. Cephradine [mi]

63. Cephradine [hsdb]

64. Cefradine [mart.]

65. Epitope Id:116210

66. Cefradine [who-dd]

67. Schembl3244

68. Chembl1604

69. Divk1c_000739

70. Cephradine, Unspecified Hydrate

71. Amy500

72. Gtpl4830

73. Cefradine [ep Monograph]

74. Dtxsid4022785

75. Hms502e21

76. Kbio1_000739

77. Ninds_000739

78. Bcpp000291

79. Sq 22022 [dihydrate]

80. Hy-b1156

81. Zinc3830515

82. Tox21_113488

83. Bdbm50370585

84. S4671

85. Akos015961130

86. Tox21_113488_1

87. Ac-1409

88. Bcp9000506

89. Ccg-208520

90. Cs-4608

91. Db01333

92. Nsc 756672

93. Idi1_000739

94. Cefradine 100 Microg/ml In Acetonitrile

95. Ncgc00183036-02

96. Ncgc00263658-01

97. 7beta-[(2r)-2-(cyclohexa-1,4-dienyl)-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic Acid

98. As-75158

99. C06897

100. C74975

101. D00264

102. 821c533

103. Q2734674

104. Cefradine, European Pharmacopoeia (ep) Reference Standard

105. Cefradine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

106. (6r,7r)-7-((r)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

107. (6r,7r)-7-((r)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

108. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino-1,4-cyclohexadien-1-ylacetyl)amino)-3-methyl-8-oxo-, (6r-(6.alpha.,7.beta.(r*)))-

109. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2r)-2-amino-2-(1,4-cyclohexadien-1-yl)acetyl]amino]-3-methyl-8-oxo-,(6r,7r)-

110. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2r)-amino-1,4-cyclohexadien-1-ylacetyl]amino]-3-methyl-8-oxo-,(6r,7r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₉N₃O₄S
Molecular Weight	349.4 g/mol
XLogP3	0.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	349.10962727 g/mol
Monoisotopic Mass	349.10962727 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	697
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 Therapeutic Uses

Cephalosporins

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Cephradine /is/ indicated in the treatment of bacterial urinary tract infections caused by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 768

Cephradine /is/ indicated in the treatment of bacterial pharyngitis caused by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 768

Cephradine /is/ indicated in the treatment of skin and soft tissue infections caused by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 268

For more Therapeutic Uses (Complete) data for CEPHRADINE (18 total), please visit the HSDB record page.

4.2 Drug Warning

Cephalosporins should be used with caution in patients with a history of GI disease, particularly colitis. Because antibiotic-associated pseudomembranous colitis has been reported with the use of cephalosporins, it should be considered in the differential diagnosis of patients who develop diarrhea during or following therapy with the drugs. /Cephalosporins/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 109

Prolonged use of a cephalosporin may result in the overgrowth of nonsusceptible organisms, especially Enterobacter, Pseudomonas, enterococci, or Candida. If superinfection occurs, appropriate therapy should be instituted. /Cephalosporins/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 109

Other adverse effects reported with cephalosporin therapy include chest pain, pleural effusion, dyspnea or respiratory distress, cough, and rhinitis. Increased or decreased serum glucose concentration also has been reported. /Cephalosporins/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 109

The most frequent adverse reactions to orally administered cephalosporins are nausea, vomiting, and diarrhea. These effects are usually mild and transient, but rarely may be severe enough to require discontinuance of the drug. Other adverse GI effects which have occurred with some of the oral cephalosporins include abdominal pain, tenesmus, epigastric pain/dyspepsia, decreased appetite/anorexia, glossitis, flatulence, candidiasis (eg, oral thrush), taste alteration, decreased salivation, and heartburn. Adverse GI effects can also occur with IM or IV cephalosporins. /Cephalosporins/

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 109

For more Drug Warnings (Complete) data for CEPHRADINE (9 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

CEPHRADINE ANHYDROUS

5.2.2 FDA UNII

9YA6SX5S4D

5.2.3 Pharmacological Classes

Chemical Structure [CS] - Cephalosporins

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB09 - Cefradine

5.4 Absorption, Distribution and Excretion

Route of Elimination

Over 90 percent of the drug is excreted unchanged in the urine within six hours.

CEPHRADINE IS ALMOST COMPLETELY ABSORBED AFTER ORAL ADMIN; IN PRESENCE OF FOOD, ABSORPTION IS SLOWED BUT NOT DECR. ORAL DOSES OF 250 & 500 MG YIELD PEAK PLASMA LEVELS OF ABOUT 9 & 16.5 UG/ML, WITHIN 40 MIN FROM EMPTY STOMACH. ABSORPTION BY IM ROUTE IS CONSIDERABLY SLOWER.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1171

AFTER SINGLE ORAL ADMIN, CEPHRADINE WAS ABSORBED RAPIDLY FROM GI TRACT & PEAK SERUM CONCN ACHIEVED WITHIN 1 HR. 75-100% OF DOSE EXCRETED UNCHANGED IN URINE IN FIRST 6 HOURS.

PMID:4591487 ZAKI A ET AL; J CLIN PHARMACOL 14: 118-26 (1974)

SIX SUBJECTS RECEIVED 1 G EACH OF CEPHRADINE (I) & CEPHALEXIN (II) EVERY 4 HR FOR 7 DOSES & 5 RECEIVED 2 G EVERY 6 HR FOR 5 DOSES. PEAK SERUM LEVELS FOR I & II WERE 29 & 35 UG/ML, RESPECTIVELY, FOLLOWING 1 G & 45-50 UG/ML FOLLOWING 2 G.

PMID:438352 CHOW M ET AL; J CLIN PHARMACOL 19: 185-194 (1979)

Cephalosporins are primarily excreted by the kidney ... . /Cephalosporins/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1088

For more Absorption, Distribution and Excretion (Complete) data for CEPHRADINE (18 total), please visit the HSDB record page.

5.5 Metabolism/Metabolites

Cephradine is not metabolized and, after rapid absorption from the gastrointestinal tract, is excreted unchanged in the urine.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1089

5.6 Mechanism of Action

Cefradine is a first generation cephalosporin antibiotic with a spectrum of activity similar to Cefalexin. Cefradine, 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 Cefradine interferes with an autolysin inhibitor.

Cephalosporins and cephamycins inhibit bacterial cell wall synthesis in a manner similar to that of penicillin. /Cephalosporins/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1085

The first generation cephalosporins ... have activity against gram positive bacteria and relatively modest activity against gram negative microorganisms. /Cephalosporins/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1085

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