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Chemistry

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Also known as: 69388-79-0, Sulbactam pivoxyl, Pivsulbactam, Sulbactam pivoxil [usan], Cp-47904, Unii-2x0wta96kx

Molecular Formula

C₁₄H₂₁NO₇S

Molecular Weight

347.39 g/mol

InChI Key

OHPVYKXTRACOSQ-ZJUUUORDSA-N

FDA UNII

2X0WTA96KX

Sulbactam Pivoxil is the pivoxil prodrug form of sulbactam, a semi-synthetic beta-lactamase inhibitor, with beta-lactam antibiotic adjuvant activity. After oral administration of sulbactam pivoxil, the ester bond is cleaved, releasing active sulbactam. The beta-lactam ring of sulbactam irreversibly binds to beta-lactamase at or near its active site, thereby blocking enzyme activity and preventing metabolism of other beta-lactam antibiotics by the enzyme.

1 2D Structure

Sulbactam Pivoxil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethylpropanoyloxymethyl (2S,5R)-3,3-dimethyl-4,4,7-trioxo-46-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C14H21NO7S/c1-13(2,3)12(18)22-7-21-11(17)10-14(4,5)23(19,20)9-6-8(16)15(9)10/h9-10H,6-7H2,1-5H3/t9-,10+/m1/s1

2.1.3 InChI Key

OHPVYKXTRACOSQ-ZJUUUORDSA-N

2.2 Other Identifiers

2.2.1 UNII

2X0WTA96KX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cp 47,904

2. Cp-47,904

3. Cp-47904

4. Sulbactam Pivoxyl

2.3.2 Depositor-Supplied Synonyms

1. 69388-79-0

2. Sulbactam Pivoxyl

3. Pivsulbactam

4. Sulbactam Pivoxil [usan]

5. Cp-47904

6. Unii-2x0wta96kx

7. Pivoxil Sulbactam

8. Sulbactam Pivoxil (usan)

9. 2x0wta96kx

10. Pivsulbactam [mart.]

11. Pivsulbactam [who-dd]

12. Cp-47,904

13. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester,4,4-dioxide, (2s,5r)-

14. Pivsulbactam (mart.)

15. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (2s-cis)-

16. Hydroxymethyl (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate Pivalate (ester), 4,4-dioxide

17. (2s,5r)-(pivaloyloxy)methyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

18. Cp 47904; Unasyn Oral

19. Cp 47904

20. (pivaloyloxy)methyl Penicillanate S,s-dioxide

21. Schembl635112

22. Chembl423875

23. Chebi:135467

24. Mfcd00867003

25. Akos025310138

26. As-13808

27. Cp 47,904

28. Hy-108288

29. Cs-0028149

30. D03706

31. E75950

32. Q27255724

33. (2s,5r)-(pivaloyloxy)methyl3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate4,4-dioxide

34. (pivaloyloxy)methyl (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

35. 2,2-dimethylpropanoyloxymethyl (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

36. 2,2-dimethylpropanoyloxymethyl 3,3-dimethyl-4,4,7-trioxo-4

37. E6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₂₁NO₇S
Molecular Weight	347.39 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	115
Heavy Atom Count	23
Formal Charge	0
Complexity	654
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