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ACTIVE PHARMA INGREDIENTS

1 KDMF

1 KDMF

FINISHED DOSAGE FORMULATIONS

2 FDF Dossiers, 2 Listed Dossiers

2 FDF Dossiers
2 Listed Dossiers

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Chemistry

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Also known as: 99665-00-6, Flomoxefum, Fmox, Flomoxef [inn], Flomoxef sodium, V9e5u5xf42

Molecular Formula

C₁₅H₁₈F₂N₆O₇S₂

Molecular Weight

496.5 g/mol

InChI Key

UHRBTBZOWWGKMK-DOMZBBRYSA-N

FDA UNII

V9E5U5XF42

Flomoxef is a cephamycin antibiotic with a difluoromethylthio-acetamido group at the 7-beta position of the cephem nucleus, commonly used for postoperative prophylaxis. Flomoxef has activity against epidermides, streptococci, propionibacteria, and both methicillin-resistant and -susceptible Staphylococcus aureus.

1 2D Structure

Flomoxef

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[2-(difluoromethylsulfanyl)acetyl]amino]-3-[[1-(2-hydroxyethyl)tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C15H18F2N6O7S2/c1-29-15(18-8(25)6-31-13(16)17)11(28)23-9(10(26)27)7(4-30-12(15)23)5-32-14-19-20-21-22(14)2-3-24/h12-13,24H,2-6H2,1H3,(H,18,25)(H,26,27)/t12-,15+/m1/s1

2.1.3 InChI Key

UHRBTBZOWWGKMK-DOMZBBRYSA-N

2.1.4 Canonical SMILES

COC1(C2N(C1=O)C(=C(CO2)CSC3=NN=NN3CCO)C(=O)O)NC(=O)CSC(F)F

2.1.5 Isomeric SMILES

CO[C@@]1([C@@H]2N(C1=O)C(=C(CO2)CSC3=NN=NN3CCO)C(=O)O)NC(=O)CSC(F)F

2.2 Other Identifiers

2.2.1 UNII

V9E5U5XF42

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Oxacephem 6315-s

2. S 6315

2.3.2 Depositor-Supplied Synonyms

1. 99665-00-6

2. Flomoxefum

3. Fmox

4. Flomoxef [inn]

5. Flomoxef Sodium

6. V9e5u5xf42

7. (6r,7r)-7-[[2-(difluoromethylsulfanyl)acetyl]amino]-3-[[1-(2-hydroxyethyl)tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

8. Flomoxef (inn)

9. Flomoxefo

10. 5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1h-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-, (6r-cis)-

11. 5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1h-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-, (6r,7r)-

12. Flomoxefum [latin]

13. Flomoxefo [spanish]

14. Unii-v9e5u5xf42

15. Ncgc00182999-01

16. Flomoxef [mi]

17. Flomoxef [who-dd]

18. Schembl49438

19. Chembl15413

20. Dtxsid5048845

21. Chebi:135813

22. Bcp20920

23. Hy-b0706

24. Zinc3874302

25. Akos015896442

26. Db11935

27. Ac-15832

28. Cs-0009596

29. D07963

30. 665f006

31. A846063

32. Q5459999

33. (-)-(6r,7r)-7-(2-((difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1h-tetrazol-5-yl)thio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

34. (6r,7r)-7-[[2-(difluoromethylthio)-1-oxoethyl]amino]-3-[[[1-(2-hydroxyethyl)-5-tetrazolyl]thio]methyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

35. (6r,7r)-7-[2-[bis(fluoranyl)methylsulfanyl]ethanoylamino]-3-[[1-(2-hydroxyethyl)-1,2,3,4-tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxidanylidene-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

36. (6r,7r)-7-{2-[(difluoromethyl)sulfanyl]acetamido}-3-({[1-(2-hydroxyethyl)-1h-tetrazol-5-yl]sulfanyl}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

37. (7r)-7-(2-(difluoromethylthio)acetamido)-3-((1-(2-hydroxyethyl)-1h-tetrazol-5-ylthio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈F₂N₆O₇S₂
Molecular Weight	496.5 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	11
Exact Mass	496.06464561 g/mol
Monoisotopic Mass	496.06464561 g/mol
Topological Polar Surface Area	220 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	793
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