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Chemistry

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Also known as: 161715-24-8, Orapenem, Tbpm-pi, Me1211, L-084, Ljc 11,084

Molecular Formula

C₂₂H₃₁N₃O₆S₂

Molecular Weight

497.6 g/mol

InChI Key

SNUDIPVBUUXCDG-QHSBEEBCSA-N

FDA UNII

95AK1A52I8

Tebipenem Pivoxil is an orally available pivaloyloxymethyl ester prodrug of tebipenem, a broad-spectrum 1-beta-methylcarbapenem antibiotic with a 1-(1,3-thiazolin-2-yl) azetidin-3-ylthio group at the C-2 position. After oral administration of tebipenem pivoxil, the ester bond is cleaved, releasing active tebipenem.

1 2D Structure

Tebipenem Pivoxil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1

2.1.3 InChI Key

SNUDIPVBUUXCDG-QHSBEEBCSA-N

2.1.4 Canonical SMILES

CC1C2C(C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)OCOC(=O)C(C)(C)C)C(C)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)OCOC(=O)C(C)(C)C)[C@@H](C)O

2.2 Other Identifiers

2.2.1 UNII

95AK1A52I8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. L 084

2. L-084

2.3.2 Depositor-Supplied Synonyms

1. 161715-24-8

2. Orapenem

3. Tbpm-pi

4. Me1211

5. L-084

6. Ljc 11,084

7. 2,2-dimethylpropanoyloxymethyl (4r,5s,6s)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

8. Ljc-11084

9. Me-1211

10. 95ak1a52i8

11. Tebipenempivoxil

12. Tebipenem [inn]

13. (4r,5s,6s)-(pivaloyloxy)methyl 3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

14. (1r,5s,6s)-6-[1(r)-hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic Acid Pivaloyloxymethyl Ester

15. Tebipenem Pivoxil (l-084)

16. Tebipenem Pivoxil [inn]

17. Tebipenem Pivoxil(l-084)

18. Unii-95ak1a52i8

19. Orapenem (tn)

20. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (4r,5s,6s)-

21. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (4r,5s,6s)-

22. Mls006011128

23. Schembl305541

24. Tebipenem Pivoxil [mi]

25. Tebipenem Pivoxil [usan:inn]

26. Tebipenem Pivoxil [jan]

27. Chembl2107486

28. Tebipenem Pivoxil [usan]

29. Gtpl10864

30. Dtxsid00167228

31. Chebi:135799

32. Tebipenem Pivoxil [who-dd]

33. Ex-a1256

34. Hy-b0396

35. Who 7924

36. Zinc4217736

37. Tebipenem Pivoxil (jan/usan/inn)

38. Ljc 11084

39. Mfcd17215369

40. S2159

41. Akos015899532

42. Ccg-269673

43. Ljc-11,084

44. Ncgc00346570-01

45. Ncgc00346570-04

46. (pivaloyloxy)methyl (4r,5s,6s)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

47. [(4r,5s,6s)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate

48. Ac-22712

49. As-75334

50. L-084;me1211

51. Smr004702908

52. L 084

53. C73086

54. D09598

55. Ab01566835_01

56. A854567

57. Q1623593

58. ((2,2-dimethylpropanoyl)oxy)methyl (4r,5s,6s)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)sulfanyl)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

59. (4r,5r,6s)-3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid (2,2-dimethyl-1-oxopropoxy) Methyl Ester

60. (4r,5s,6s)-(pivaloyloxy)methyl3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

61. 2,2-dimethylpropanoyloxymethyl (4r,5s,6s)-3-[1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₁N₃O₆S₂
Molecular Weight	497.6 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	10
Exact Mass	497.16542806 g/mol
Monoisotopic Mass	497.16542806 g/mol
Topological Polar Surface Area	159 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	908
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DH - Carbapenems

J01DH06 - Tebipenem pivoxil

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