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Chemistry

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Also known as: Floxacillin, 5250-39-5, Floxapen, Flucloxacilina, Flucloxacilline, Flucloxacillinum
Molecular Formula
C19H17ClFN3O5S
Molecular Weight
453.9  g/mol
InChI Key
UIOFUWFRIANQPC-JKIFEVAISA-N
FDA UNII
43B2M34G2V

Floxacillin
Antibiotic analog of CLOXACILLIN.
1 2D Structure

Floxacillin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,5R,6R)-6-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
2.1.3 InChI Key
UIOFUWFRIANQPC-JKIFEVAISA-N
2.1.4 Canonical SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
2.1.5 Isomeric SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
43B2M34G2V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Floxacillin

2. Fluorochloroxacillin

2.3.2 Depositor-Supplied Synonyms

1. Floxacillin

2. 5250-39-5

3. Floxapen

4. Flucloxacilina

5. Flucloxacilline

6. Flucloxacillinum

7. Floxacillin [usan]

8. Flucloxacillin Sodium

9. Flucloxacilina [inn-spanish]

10. Flucloxacilline [inn-french]

11. Flucloxacillinum [inn-latin]

12. Brl 2039

13. 3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin

14. Flucloxacillin-sodium

15. Chebi:5098

16. Floxacillin (usan)

17. Flucloxacillin (inn)

18. Flucloxacillin [inn]

19. Brl-2039

20. Floxapen (tn)

21. (2s,5r,6r)-6-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

22. 43b2m34g2v

23. (2s,5r,6r)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

24. 6-(3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

25. Floxacillin Sodium Anhydrous

26. Flucloxacillin Sodium Anhydrous

27. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,6-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,(2s,5r,6r)-

28. Mfipc

29. Nsc-277175

30. Einecs 226-051-0

31. Unii-43b2m34g2v

32. Flucloxacillin,(s)

33. Floxacillin [mi]

34. Epitope Id:117416

35. Schembl3823

36. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2s(2alpha,5alpha,6beta))

37. Flucloxacillin [mart.]

38. Chembl222645

39. Flucloxacillin [who-dd]

40. Dtxsid8023056

41. Gtpl10910

42. Brl2039

43. Hy-a0246

44. Zinc4102187

45. Bdbm50370590

46. Db00301

47. Ncgc00485420-01

48. (2s,5r,6r)-6-({[3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

49. (2s,5r,6r)-6-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

50. 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido]-2,2-dimethylpenam-3alpha-carboxylic Acid

51. Nci60_002254

52. Cs-0017591

53. D04196

54. 250f395

55. Q1994556

56. W-105817

57. Brd-k27871792-001-01-8

58. Flucloxacillin, Antibiotic For Culture Media Use Only

59. (2s,5r,6r)-6-(3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

60. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2s(2.alpha.,5.alpha.,6.beta.))

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 453.9 g/mol
Molecular Formula C19H17ClFN3O5S
XLogP32.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass453.0561477 g/mol
Monoisotopic Mass453.0561477 g/mol
Topological Polar Surface Area138 Ų
Heavy Atom Count30
Formal Charge0
Complexity758
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Used to treat bacterial infection by susceptible microorganisms.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Flucloxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Flucloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Flucloxacillin results from the inhibition of cell wall synthesis and is mediated through flucloxacillin binding to penicillin binding proteins (PBPs). Flucloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 ATC Code

J01CF05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CF - Beta-lactamase resistant penicillins

J01CF05 - Flucloxacillin


5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability is 5070% following oral administration.


5.5 Metabolism/Metabolites

Hepatic.


Flucloxacillin has known human metabolites that include 6-[[3-(2-Chloro-6-fluorophenyl)-5-(hydroxymethyl)-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

0.751 hour


5.7 Mechanism of Action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, flucloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that flucloxacillin interferes with an autolysin inhibitor.


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06-Jan-2021
30-Oct-2024
KGS
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