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Technical details about Cefpodoxime Proxetil, learn more about the structure, uses, toxicity, action, side effects and more

Cefpodoxime Proxetil

Synopsis, Chemistry

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ANALYTICAL SOLUTION(s)

3 EDQM Standards, 1 USP Standards, 1 Other Ref. Standards

DIGITAL CONTENT

3 Data Compilation & Company Tracker #PharmaFlow, 3 News

Also known as: Vantin, Banan, 87239-81-4, Orelox, Doxef, Cs-807

Molecular Formula

C₂₁H₂₇N₅O₉S₂

Molecular Weight

557.6 g/mol

InChI Key

LTINZAODLRIQIX-FBXRGJNPSA-N

FDA UNII

2TB00A1Z7N

Cefpodoxime Proxetil is a third generation semi-synthetic cephalosporin and a beta-lactam antibiotic with bactericidal activity. Cefpodoxime's effect is dependent on its binding to penicillin-binding proteins (PBPs) located in the bacterial cytoplasmic membrane. Binding results in the inhibition of the transpeptidase enzymes, thereby preventing cross-linking of the pentaglycine bridge with the fourth residue of the pentapeptide and interrupting consequent synthesis of peptidoglycan chains. As a result, cefpodoxime inhibits bacterial septum and cell wall synthesis formation.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13-/t10?,14-,18-/m1/s1

2.1.3 InChI Key

LTINZAODLRIQIX-FBXRGJNPSA-N

2.1.4 Canonical SMILES

CC(C)OC(=O)OC(C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CSC(=N3)N)COC

2.1.5 Isomeric SMILES

CC(C)OC(=O)OC(C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC)/C3=CSC(=N3)N)COC

2.2 Other Identifiers

2.2.1 UNII

2TB00A1Z7N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(isopropoxycarbonyloxy)ethyl-7-(2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido)-3-methoxymethyl-8-oxo-5-thia-1-azabicyclo(4,2,0)-oct-2-ene-2-carboxylate

2. Cephalosporin 807

3. Cs 807

4. Cs-807

5. Doxef

6. U 76252

7. U-76,252

8. Vantin

2.3.2 Depositor-Supplied Synonyms

1. Vantin

2. Banan

3. 87239-81-4

4. Orelox

5. Doxef

6. Cs-807

7. Simplicef

8. Otreon

9. U-76252

10. Podomexef

11. Chebi:3505

12. 2tb00a1z7n

13. Cefodox

14. Nsc-759161

15. (rs)-1-((isopropoxycarbonyl)oxy)ethyl (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)-2-((z)-methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

16. Dsstox_cid_2766

17. Dsstox_rid_76722

18. Cefpodoxime 1-(isopropyloxycarbonyloxy)ethyl Ester

19. Dsstox_gsid_22766

20. Xtum-o

21. 1-{[(propan-2-yloxy)carbonyl]oxy}ethyl (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

22. 1-{[(propan-2-yloxy)carbonyl]oxy}ethyl 7beta-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-3,4-didehydrocepham-4-carboxylate

23. Cas-87239-81-4

24. Simplicef [veterinary]

25. Unii-2tb00a1z7n

26. Orelox Paed

27. Ncgc00164598-01

28. Ncgc00183131-01

29. Mfcd00865088

30. Vantin (tn)

31. Cefpodoxime Proxetil [usan:usp:jan]

32. Schembl27071

33. Mls001401428

34. Chembl1201016

35. Dtxsid1022766

36. Cefpodoxime (as Proxetil)

37. Cefpodoxime Proxetil (jp17/usp)

38. Cefpodoxime Proxetil [jan]

39. Hms3715j22

40. Cefpodoxime Proxetil [usan]

41. Cefpodoxime Proxetil, Vantin

42. Hy-n7101

43. Cefpodoxime Proxetil [vandf]

44. Tox21_113377

45. Tox21_113428

46. Bdbm50248233

47. Cefpodoxime Proxetil [mart.]

48. S5350

49. Cefpodoxime Proxetil [usp-rs]

50. Cefpodoxime Proxetil [who-dd]

51. Akos015994692

52. Ccg-221250

53. Ks-1149

54. Nsc 759161

55. Cefpodoxime Proxetil [green Book]

56. (+-)-1-hydroxyethyl (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(z)-(o-methyloxime), Isopropyl Carbonate (ester)

57. Cefpodoxime Proxetil [orange Book]

58. Ru-51807

59. Smr000469193

60. Cefpodoxime Proxetil [ep Monograph]

61. Cefpodoxime Proxetil [usp Impurity]

62. Cefpodoxime Proxetil [usp Monograph]

63. Cefpodoxime Proxetil For Peak Identification

64. Cs-0027614

65. C08115

66. D00920

67. Ab01209734-01

68. 239c814

69. A842048

70. Cefpodoxime Proxetil For Impurity H Identification

71. Cefpodoxime 1-(isopropoxycarbonyloxy)ethyl Ester

72. Cefpodoxime 1-(isopropoxycarbonyloxy)ethyl Ester [mi]

73. (+/-)-1-hydroxyethyl (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7 (sup 2)-(z)-(o-methyloxime), Isopropyl Carbonate (ester)

74. (6r,7r)-1-((isopropoxycarbonyl)oxy)ethyl 7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

75. (6r,7r)-7-(((2z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid 1-(((1-methylethoxy)carbonyl)oxy)ethyl Ester

76. 1-({[(1-methylethyl)oxy]carbonyl}oxy)ethyl (6r,7r)-7-({(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-3-[(methyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

77. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl Ester, (6r-(6.alpha.,7.beta.(z)))-

78. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl Ester, (6r-(6alpha,7beta(z)))-

79. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-, 1-[[(1-methylethoxy)carbonyl]oxy]ethyl Ester, (6r,7r)-

2.4 Create Date

2006-05-03

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₇N₅O₉S₂
Molecular Weight	557.6 g/mol
XLogP3	0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	13
Exact Mass	557.12501980 g/mol
Monoisotopic Mass	557.12501980 g/mol
Topological Polar Surface Area	235 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	976
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Cefpodoxime proxetil
PubMed Health	Cefpodoxime Proxetil (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefpodoxime proxetil is an orally administered, extended spectrum, semi-synthetic antibiotic of the cephalosporin class. The chemical name is (RS)-1(isopropoxycarbonyloxy) ethyl (+)-(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-{(Z)methoxyimino}acetamido]-3-m...
Active Ingredient	Cefpodoxime proxetil
Dosage Form	Tablet; For suspension
Route	Oral
Strength	eq 100mg base; eq 200mg base; eq 100mg base/5ml; eq 50mg base/5ml
Market Status	Prescription
Company	Ranbaxy; Aurobindo Pharma; Sandoz; Orchid Hlthcare

2 of 2
Drug Name	Cefpodoxime proxetil
PubMed Health	Cefpodoxime Proxetil (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefpodoxime proxetil is an orally administered, extended spectrum, semi-synthetic antibiotic of the cephalosporin class. The chemical name is (RS)-1(isopropoxycarbonyloxy) ethyl (+)-(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-{(Z)methoxyimino}acetamido]-3-m...
Active Ingredient	Cefpodoxime proxetil
Dosage Form	Tablet; For suspension
Route	Oral
Strength	eq 100mg base; eq 200mg base; eq 100mg base/5ml; eq 50mg base/5ml
Market Status	Prescription
Company	Ranbaxy; Aurobindo Pharma; Sandoz; Orchid Hlthcare

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 Pharmacological Classes

Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]

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