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Prestwick3_000470

Prestwick3_000470

Synopsis, Chemistry

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Also known as: 60925-61-3, Precef, Ceforanido, Ceforanidum, Ceforanidum [inn-latin], Ceforanido [inn-spanish]

Molecular Formula

C₂₀H₂₁N₇O₆S₂

Molecular Weight

519.6 g/mol

InChI Key

SLAYUXIURFNXPG-CRAIPNDOSA-N

FDA UNII

8M1YF8951V

Ceforanide is a semi-synthetic, broad-spectrum, beta-lactam, second-generation cephalosporin antibiotic with bactericidal activity. Ceforanide causes inhibition of bacterial cell wall synthesis by inactivating penicillin binding proteins (PBPs) thereby interfering with the final transpeptidation step required for cross-linking of peptidoglycan units which are a component of the cell wall. This results in a reduction of cell wall stability and causes cell lysis.

1 2D Structure

Prestwick3_000470

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1

2.1.3 InChI Key

SLAYUXIURFNXPG-CRAIPNDOSA-N

2.1.4 Canonical SMILES

C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3CN)C(=O)O)CSC4=NN=NN4CC(=O)O

2.1.5 Isomeric SMILES

C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3CN)C(=O)O)CSC4=NN=NN4CC(=O)O

2.2 Other Identifiers

2.2.1 UNII

8M1YF8951V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7-(alpha-(2-aminomethylphenyl)acetamido)-3-((1-carboxymethyltetrazol-5-ylthio)methyl)-3-cephem-4-carboxylic Acid

2. Bl-s 786

3. Bl-s786r

4. Cefaronide

5. Ceforanide, Monosodium Salt

2.3.2 Depositor-Supplied Synonyms

1. 60925-61-3

2. Precef

3. Ceforanido

4. Ceforanidum

5. Ceforanidum [inn-latin]

6. Ceforanido [inn-spanish]

7. Bl-s786

8. (6r,7r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

9. Chebi:3495

10. 7-(o-(aminomethyl)phenylacetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic Acid

11. 8m1yf8951v

12. Nsc-760049

13. (6r,7r)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-1h-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

14. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-trans)-

15. 7-[o-(aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1h-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic Acid

16. 7beta-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1h-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic Acid

17. Bl-s 786

18. Precef (tn)

19. Ceforanide (usp/inn)

20. Sr-01000872614

21. Unii-8m1yf8951v

22. Ceforanide [usan:usp:inn:ban]

23. Ncgc00016897-01

24. Cas-60925-61-3

25. (6r,7r)-7-(2-(alpha-amino-o-tolyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

26. Ceforanide [mi]

27. Ceforanide [inn]

28. Prestwick0_000470

29. Prestwick1_000470

30. Prestwick2_000470

31. Prestwick3_000470

32. Ceforanide [usan]

33. Dsstox_cid_2760

34. Ceforanide [vandf]

35. Ceforanide [mart.]

36. Ceforanide(200mg)

37. Ceforanide [usp-rs]

38. Ceforanide [who-dd]

39. Dsstox_rid_76719

40. Dsstox_gsid_22760

41. Bspbio_000580

42. (6r-trans)-7-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

43. Schembl122072

44. Spbio_002519

45. Bpbio1_000638

46. Ceforanide [orange Book]

47. Chembl1201046

48. Dtxsid1022760

49. Gtpl12218

50. Ceforanide [usp Impurity]

51. Hms1569m22

52. Hms2096m22

53. Hms3713m22

54. (6r,7r)-7-(2-(2-(aminomethyl)phenyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

55. Hy-b1297

56. Zinc3830434

57. Tox21_110670

58. Ccg-220470

59. Db00923

60. Nsc 760049

61. Ncgc00179514-05

62. (6r,7r)-7-({[2-(aminomethyl)phenyl]acetyl}amino)-3-({[1-(carboxymethyl)-1h-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

63. (6r,7r)-7-({[2-(aminomethyl)phenyl]acetyl}amino)-3-({[1-(carboxymethyl)-1h-tetrazol-5-yl]thio}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

64. As-15783

65. Ab00513845

66. Cs-0013066

67. S5081

68. C06884

69. D00259

70. D81832

71. 925c613

72. A913663

73. Q5057287

74. Sr-01000872614-2

75. Sr-01000872614-3

76. Brd-k37848908-001-03-1

77. (6r,7r)-7-(2-(.alpha.-amino-o-tolyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

78. (6r,7r)-7-(2-(2-(aminomethyl)phenyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

79. 7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₁N₇O₆S₂
Molecular Weight	519.6 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	10
Exact Mass	519.09947376 g/mol
Monoisotopic Mass	519.09947376 g/mol
Topological Polar Surface Area	244 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	905
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Indication

For the treatment of infections caused by susceptible organisms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ceforanide is a semisynthetic second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins.

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 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DC - Second-generation cephalosporins

J01DC11 - Ceforanide

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following intramuscular injection.

5.5 Metabolism/Metabolites

The major drug elimination route was urinary excretion with 85% of the dose being excreted unchanged in the urine within 12 hr, and no metabolites with antibiotic activity were observed in urine.

5.6 Biological Half-Life

2.6 to 2.98 hours

5.7 Mechanism of Action

The bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).