CAS 117467-28-4

Chemistry, 1 End Use API, 9 Related Intermediates

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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 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

CAS 117467-28-4

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 Formula	C₂₅H₂₈N₆O₇S₃
Molecular Weight	620.7 g/mol
XLogP3	4.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	12
Exact Mass	620.11816077 g/mol
Monoisotopic Mass	620.11816077 g/mol
Topological Polar Surface Area	257 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	1160
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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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CAS Number

104146-10-3

End Use API

Cephalosporin

About the Company

Hubei Ling Sheng Pharmaceutical Co., Ltd. was established in December 29, 2010, the company is located in...

Hubei Ling Sheng Pharmaceutical Co., Ltd. was established in December 29, 2010, the company is located in Xiangyang City, Hubei Province Xiangcheng Economic Development Zone, is a key intermediate cephalosporin antibiotics, APIs, DDP-4 hypoglycemic agents , Development, production and sales of specialized pharmaceutical companies. In 2016 the company obtained the national high-tech enterprise certification. Company under the Hubei Ling Sheng Pharmaceutical Co., Ltd. Wuhan Branch. The company has the core technology, is currently the industry's major oral cephalosporin antibiotics API production base.

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Cephalosporin

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Nantong Chem-land Co., Ltd. is located in Nantong city, a developed port city which distance from Shangha...

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