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Floxacillin

Synopsis, 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

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 Formula	C₁₉H₁₇ClFN₃O₅S
Molecular Weight	453.9 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	453.0561477 g/mol
Monoisotopic Mass	453.0561477 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	758
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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

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.