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Also known as: Spectracef, 117467-28-4, Cefditoren pivaloyloxymethyl ester, Cdtr-pi, Meiact, Cefditoren (pivoxil)
Molecular Formula
C25H28N6O7S3
Molecular Weight
620.7  g/mol
InChI Key
AFZFFLVORLEPPO-UVYJNCLZSA-N
FDA UNII
78THA212DH

Cefditoren Pivoxil
Cefditoren Pivoxil is a semi-synthetic, broad-spectrum, beta-lactamase resistant, third-generation cephalosporin antibiotic with bactericidal activity. Cefditoren pivoxil is a prodrug that is rapidly hydrolyzed by intestinal esterases during absorption to the microbiologically active cefditoren, an active aminothiazolyl cephalosporin. Cefditoren inactivates penicillin binding proteins (PBPs) thereby interfering with peptidoglycan synthesis and inhibiting bacterial cell wall synthesis. Another consequence of beta-lactam exposure results in the loss of lipoteichoic acids from the cell wall. Lipoteichoic acids inhibit murein hydrolase activity and their absence from the cell wall triggers uncontrolled autolytic activity rendering bacterial cells susceptible to osmotic shock. This results in a reduction of cell wall stability and causes cell lysis.
1 2D Structure

Cefditoren Pivoxil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C25H28N6O7S3/c1-12-15(41-10-27-12)7-6-13-8-39-21-17(29-19(32)16(30-36-5)14-9-40-24(26)28-14)20(33)31(21)18(13)22(34)37-11-38-23(35)25(2,3)4/h6-7,9-10,17,21H,8,11H2,1-5H3,(H2,26,28)(H,29,32)/b7-6-,30-16-/t17-,21-/m1/s1
2.1.3 InChI Key
AFZFFLVORLEPPO-UVYJNCLZSA-N
2.1.4 Canonical SMILES
CC1=C(SC=N1)C=CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
2.1.5 Isomeric SMILES
CC1=C(SC=N1)/C=C\C2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
2.2 Other Identifiers
2.2.1 UNII
78THA212DH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (-)-(6r,7r)-2,2-dimethylpropionyloxymethyl 7-((z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido)-3-((z)-2-(4-methylthiazol-5-yl)ethenyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

2. 7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(2-(4-methylthiazol-5-yl)ethenyl)cephem-4-carboxylic Acid Pivaloyloxymethyl Ester

3. Cdtr-pi

4. Me 1207

5. Me-1207

6. Spectracef

2.3.2 Depositor-Supplied Synonyms

1. Spectracef

2. 117467-28-4

3. Cefditoren Pivaloyloxymethyl Ester

4. Cdtr-pi

5. Meiact

6. Cefditoren (pivoxil)

7. Cefditoren Pivoxil [jan]

8. Me-1207

9. Cefditorin Pivoxil

10. Me1207

11. Cefditoren Pivoxil Hcl

12. 78tha212dh

13. Cefditorin

14. Chebi:560555

15. Me 1207

16. Nsc-759098

17. 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

18. Cefditoren Pi Voxil

19. Cefditoren-pivoxil

20. [(2,2-dimethylpropanoyl)oxy]methyl (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

21. [(2,2-dimethylpropanoyl)oxy]methyl 7beta-(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-3,4-didehydrocepham-4-carboxylic Acid

22. 1448435-17-3

23. Pivaloyloxymethyl (+)-(6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

24. Ccris 7768

25. Unii-78tha212dh

26. Spectracef (tn)

27. Ncgc00095175-01

28. Meiact (tn)

29. Mfcd00933166

30. Dsstox_cid_28669

31. Dsstox_rid_82939

32. Dsstox_gsid_48743

33. Schembl182876

34. Chembl454446

35. Cefditoren Pivoxil [usan:jan]

36. Dtxsid2048743

37. Cefditoren Pivoxil [usan]

38. Cefditoren Pivoxil (jp17/usan)

39. Cefditoren Pivoxil [vandf]

40. Cefditoren Pivoxil [mart.]

41. Cefditoren Pivoxil [who-dd]

42. Tox21_113197

43. Hy-17452a

44. S1768

45. Akos025311444

46. Ccg-270254

47. Cs-1949

48. Nsc 759098

49. Cefditoren Pivoxil [orange Book]

50. Ncgc00095175-08

51. (pivaloyloxy)methyl (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

52. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((1z)-2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-,2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

53. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r-(3(z),6-alpha,7-beta-(z)))-

54. As-12951

55. B2086

56. Cas-117467-28-4

57. Cefditoren Pivaloyloxymethyl Ester [mi]

58. D01628

59. Ab01274730-01

60. Ab01274730_02

61. 467c284

62. Brd-k72167406-001-03-9

63. (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-((z)-2-(4-methyl-5-thiazolyl)vinyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Pivaloyloxy Methyl Ester, 7(sup 2)-(z)-(o-methyloxime)

64. (6r,7r)-(pivaloyloxy)methyl 7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

65. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(((2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((1z)-2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

2.4 Create Date
2006-04-28
3 Chemical and Physical Properties
Molecular Weight 620.7 g/mol
Molecular Formula C25H28N6O7S3
XLogP34.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count14
Rotatable Bond Count12
Exact Mass620.11816077 g/mol
Monoisotopic Mass620.11816077 g/mol
Topological Polar Surface Area257 Ų
Heavy Atom Count41
Formal Charge0
Complexity1160
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameSpectracef
PubMed HealthCefditoren Pivoxil (By mouth)
Drug ClassesAntibiotic
Drug LabelSPECTRACEF tablets contain cefditoren pivoxil, a semi-synthetic cephalosporin antibiotic for oral administration. It is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cef...
Active IngredientCefditoren pivoxil
Dosage FormTablet
RouteOral
Strength200mg; 400mg
Market StatusPrescription
CompanyVansen Pharma

2 of 2  
Drug NameSpectracef
PubMed HealthCefditoren Pivoxil (By mouth)
Drug ClassesAntibiotic
Drug LabelSPECTRACEF tablets contain cefditoren pivoxil, a semi-synthetic cephalosporin antibiotic for oral administration. It is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cef...
Active IngredientCefditoren pivoxil
Dosage FormTablet
RouteOral
Strength200mg; 400mg
Market StatusPrescription
CompanyVansen Pharma

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.)


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27-Jan-2021
23-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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