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Faropenem Medoxomil

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Also known as: 141702-36-5, Faropenem medoxomil, Faropenem medoxil, Sun-a0026, Fropenem daloxate, Faropenem medoxomil [usan]

Molecular Formula

C₁₇H₁₉NO₈S

Molecular Weight

397.4 g/mol

InChI Key

JQBKWZPHJOEQAO-DVPVEWDBSA-N

FDA UNII

5OK523O4FU

Faropenem Medoxomil is a daloxate ester prodrug form of faropenem, a penem with a tetrahydrofuran substituent at position C2, with broad-spectrum antibacterial activity against many gram-positive and gram-negative aerobes and anaerobes. Faropenem medoxomil is hydrolyzed in vivo to release the active free acid. 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 Medoxomil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C17H19NO8S/c1-7(19)11-14(20)18-12(13(27-15(11)18)9-4-3-5-23-9)16(21)24-6-10-8(2)25-17(22)26-10/h7,9,11,15,19H,3-6H2,1-2H3/t7-,9-,11+,15-/m1/s1

2.1.3 InChI Key

JQBKWZPHJOEQAO-DVPVEWDBSA-N

2.1.4 Canonical SMILES

CC1=C(OC(=O)O1)COC(=O)C2=C(SC3N2C(=O)C3C(C)O)C4CCCO4

2.1.5 Isomeric SMILES

CC1=C(OC(=O)O1)COC(=O)C2=C(S[C@H]3N2C(=O)[C@@H]3[C@@H](C)O)[C@H]4CCCO4

2.2 Other Identifiers

2.2.1 UNII

5OK523O4FU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. A0026

2. Bay 56-6854

3. Bay 566854

4. Bay-56-6854

5. Bay-566854

6. Bay56-6854

7. Bay566854

8. Faropenem Medoxomil

9. Sun 208

10. Sun A0026

11. Sun-208

12. Sun-a0026

13. Sun208

2.3.2 Depositor-Supplied Synonyms

1. 141702-36-5

2. Faropenem Medoxomil

3. Faropenem Medoxil

4. Sun-a0026

5. Fropenem Daloxate

6. Faropenem Medoxomil [usan]

7. Bay-56-6854

8. A-0026

9. 5ok523o4fu

10. (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

11. A0026

12. Sun-208

13. Faropenem Medoxomil (usan)

14. Orapem

15. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)-

16. Unii-5ok523o4fu

17. Faropenem-medoxomil

18. Bay 566854

19. Bay 56-6854

20. A 0026

21. Schembl2334640

22. Sun208

23. Faropenem Daloxate [mi]

24. Chembl1257070

25. Sun A0026

26. Sun 208

27. Chebi:134710

28. Zinc3806644

29. Bay566854

30. Bay-566854

31. Bay56-6854

32. Cs-0390

33. Db05659

34. Hy-10004

35. D08919

36. 702f365

37. A911194

38. Q27095691

39. (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

40. (5-methyl-2-oxo-1,3-dioxoren-4-yl)methyl(5r,6s)-6-((r)-1-hydroxyethyl)-7-oxo-3-((r)-2-tetrahydrofuryl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

41. (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolane-2-yl]-4-thia-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic Acid 5-methyl-2-oxo-1,3-dioxole-4-ylmethyl Ester

42. 4-thia-1-azabicyclo(.32.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)-

43. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)

44. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r-(3(r*),5alpha,6alpha(r*)))-

45. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₉NO₈S
Molecular Weight	397.4 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	397.08313774 g/mol
Monoisotopic Mass	397.08313774 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	775
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 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in bacterial infection, bronchitis, otitis media, and pediatric indications.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Faropenem has demonstrated excellent in vitro activity against common respiratory pathogens, many aerobic gram-positive organisms, and anaerobes. Activity against gram-negative organisms is more reserved. In vivo data suggest that faropenem is efficacious in treating community-acquired infections including uncomplicated skin and skin structure infections; however, more data may help to characterize faropenem's place in antimicrobial therapy.

5.2 Mechanism of Action

Like other beta-lactam antibiotics, faropenem acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis.

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