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Also known as: Fropenem, 106560-14-9, Faropenem sodium, Faropenem sodium hydrate, (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Molecular Formula

C₁₂H₁₅NO₅S

Molecular Weight

285.32 g/mol

InChI Key

HGGAKXAHAYOLDJ-FHZUQPTBSA-N

FDA UNII

F52Y83BGH3

Faropenem is a penem with a tetrahydrofuran substituent at position C2, with broad-spectrum antibacterial activity against many gram-positive and gram-negative aerobes and anaerobes. Compared with imipenem, faropenem has improved chemical stability and reduced central nervous system effects. In addition, faropenem is resistant to hydrolysis by many beta-lactamases.

1 2D Structure

Faropenem

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1

2.1.3 InChI Key

HGGAKXAHAYOLDJ-FHZUQPTBSA-N

2.1.4 Canonical SMILES

CC(C1C2N(C1=O)C(=C(S2)C3CCCO3)C(=O)O)O

2.1.5 Isomeric SMILES

C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)[C@H]3CCCO3)C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

F52Y83BGH3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (5r,6s)-6-(r)-1-hydroxyethyl-7-oxo-3-(r)-2-tetrahydrofuryl-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

2. Fropenem

2.3.2 Depositor-Supplied Synonyms

1. Fropenem

2. 106560-14-9

3. Faropenem Sodium

4. Faropenem Sodium Hydrate

5. (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

6. (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

7. Chebi:51257

8. F52y83bgh3

9. (+)-(5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

10. 122547-49-3

11. Ncgc00164546-02

12. 122547-49-3 (na)

13. Dsstox_cid_26430

14. Dsstox_rid_81608

15. Dsstox_gsid_46430

16. (5r,6s)-6-((r)-1-hydroxyethyl)-7-oxo-3-((r)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

17. 6alpha-[(1r)-1-hydroxyethyl]-2-[(2r)-tetrahydrofuran-2-yl]-2,3-didehydropenam-3-carboxylic Acid

18. 6alpha-[(r)-1-hydroxyethyl]-2-[(r)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic Acid

19. Fropenem [inn]

20. (5r,6s)-6-(1-hydroxyethyl)-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

21. Cas-106560-14-9

22. Faropenem [usan:inn]

23. Unii-f52y83bgh3

24. Ncgc00164546-01

25. (5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

26. Faropenem [inn]

27. Faropenem [mi]

28. Faropenem [who-dd]

29. Schembl239381

30. Chembl556262

31. Dtxsid0046430

32. Gtpl10808

33. Hy-a0035

34. Zinc3959242

35. Tox21_112175

36. Bdbm50483324

37. Compound 1 [pmid: 9216830]

38. Akos015895072

39. Tox21_112175_1

40. Db12190

41. Cs-0006739

42. H11961

43. 560f149

44. A801462

45. Sr-01000872591

46. J-001609

47. Q1397045

48. Sr-01000872591-1

49. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-,(5r,6s)

50. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid,6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5r,6s)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₅NO₅S
Molecular Weight	285.32 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	285.06709375 g/mol
Monoisotopic Mass	285.06709375 g/mol
Topological Polar Surface Area	112 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	477
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

J01DI - Other cephalosporins and penems

J01DI03 - Faropenem

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