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Also known as: 105889-45-0, Cefcapene piroxil, Cefcapene-pivoxil, Flomox, 8i8mj56xfq, 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Molecular Formula

C₂₃H₂₉N₅O₈S₂

Molecular Weight

567.6 g/mol

InChI Key

WVPAABNYMHNFJG-QDVBXLKVSA-N

FDA UNII

8I8MJ56XFQ

Cefcapene Pivoxil is the pivalate ester prodrug form of cefcapene, a semi-synthetic third-generation cephalosporin with antibacterial activity. After oral administration of cefcapene pivoxil, the ester bond is cleaved, releasing active cefcapene.

1 2D Structure

Cefcapene Pivoxil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6-/t14-,18-/m1/s1

2.1.3 InChI Key

WVPAABNYMHNFJG-QDVBXLKVSA-N

2.1.4 Canonical SMILES

CCC=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C

2.1.5 Isomeric SMILES

CC/C=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C

2.2 Other Identifiers

2.2.1 UNII

8I8MJ56XFQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. S 1108

2. S-1108

2.3.2 Depositor-Supplied Synonyms

1. 105889-45-0

2. Cefcapene Piroxil

3. Cefcapene-pivoxil

4. Flomox

5. 8i8mj56xfq

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

7. S-1108

8. Cefcamate Pivoxil

9. Unii-8i8mj56xfq

10. 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-(((z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl)amino)-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

11. Schembl155121

12. Schembl155122

13. Chembl2431072

14. Dtxsid7049134

15. Cefcapene Pivoxil [who-dd]

16. Zinc3924558

17. Akos015841961

18. Akos015896113

19. Hy-135221a

20. Cefcapene Pivaloyloxymethyl Ester

21. As-12938

22. Cs-0111083

23. Cefcapene Pivaloyloxymethyl Ester [mi]

24. 889c450

25. A801331

26. Q27270575

27. 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(z)-2-(2-aminothiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;cefcapene Pivoxil

28. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-(((2z)-2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl)amino)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

29. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl)amino)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r-(6alpha,7beta(z)))-

2.4 Create Date

2005-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₉N₅O₈S₂
Molecular Weight	567.6 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	13
Exact Mass	567.14575525 g/mol
Monoisotopic Mass	567.14575525 g/mol
Topological Polar Surface Area	247 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	1060
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1