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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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03-Jan-2022
30-Jun-2025
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Floxacillin manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Floxacillin API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Floxacillin manufacturer or Floxacillin supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Floxacillin manufacturer or Floxacillin supplier.

PharmaCompass also assists you with knowing the Floxacillin API Price utilized in the formulation of products. Floxacillin API Price is not always fixed or binding as the Floxacillin Price is obtained through a variety of data sources. The Floxacillin Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Floxacillin

Synonyms

5250-39-5, Floxapen, Flucloxacilina, Flucloxacilline, Flucloxacillinum, Floxacillin [usan]

Cas Number

5250-39-5

Unique Ingredient Identifier (UNII)

43B2M34G2V

About Floxacillin

Antibiotic analog of CLOXACILLIN.

Staphylex Manufacturers

A Staphylex manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Staphylex, including repackagers and relabelers. The FDA regulates Staphylex manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Staphylex API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Staphylex manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Staphylex Suppliers

A Staphylex supplier is an individual or a company that provides Staphylex active pharmaceutical ingredient (API) or Staphylex finished formulations upon request. The Staphylex suppliers may include Staphylex API manufacturers, exporters, distributors and traders.

click here to find a list of Staphylex suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Staphylex CEP

A Staphylex CEP of the European Pharmacopoeia monograph is often referred to as a Staphylex Certificate of Suitability (COS). The purpose of a Staphylex CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Staphylex EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Staphylex to their clients by showing that a Staphylex CEP has been issued for it. The manufacturer submits a Staphylex CEP (COS) as part of the market authorization procedure, and it takes on the role of a Staphylex CEP holder for the record. Additionally, the data presented in the Staphylex CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Staphylex DMF.

A Staphylex CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Staphylex CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Staphylex suppliers with CEP (COS) on PharmaCompass.

Staphylex GMP

Staphylex Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Staphylex GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Staphylex GMP manufacturer or Staphylex GMP API supplier for your needs.

Staphylex CoA

A Staphylex CoA (Certificate of Analysis) is a formal document that attests to Staphylex's compliance with Staphylex specifications and serves as a tool for batch-level quality control.

Staphylex CoA mostly includes findings from lab analyses of a specific batch. For each Staphylex CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Staphylex may be tested according to a variety of international standards, such as European Pharmacopoeia (Staphylex EP), Staphylex JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Staphylex USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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