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Flucloxacillin

Flucloxacillin structure

Flucloxacillin 

structure
  • CAS No:

    5250-39-5

  • Formula:

    C19H17ClFN3O5S

  • Chemical Name:

    Flucloxacillin

  • Synonyms:

    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)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,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,6-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,[2S-(2α,5α,6β)]-;(2S,5R,6R)-6-[[[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;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;Flucloxacillin;[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]penicillin;Floxacillin;BRL 2039;6-[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolecarboxamido]penicillanic acid;Culpen;FK 900;Fluoxacillin;Staphlipen;Penplus;Abboflox;Flupen

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

ChEBI: A penicillin compound having a 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain.


Solid


Flucloxacillin is a penicillin compound having a 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a flucloxacillin(1-).|Antibiotic analog of [cloxacillin].|Flucloxacillin is a narrow-spectrum, semisynthetic isoxazolyl penicillin with antibacterial activity. Floxacillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.|Antibiotic analog of CLOXACILLIN.

Flucloxacillin Basic Attributes

453.87

453.87

226-051-0

43B2M34G2V

DTXSID8023056

C80591

J01CF05|J - Antiinfectives for systemic use

Characteristics

138

3.2

Solid

1.6±0.1 g/cm3

677.3±55.0 °C at 760 mmHg

363.4±31.5 °C

1.672

5.45e-02 g/L

Safety Information

P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501

H317

|Danger|H317 (96.55%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 58 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Three forms of liver injury have been attributed to the penicillinase-resistant and other penicillins. The first is a transient and usually asymptomatic elevation in serum aminotransferase levels that occurs with high dose intravenous therapy with oxacillin (Case 1, Oxacillin) and rarely with standard penicillins (Case 1, Penicillin G). This reaction has not been described with nafcillin or dicloxacillin and patients can be safety switched to these or other forms of penicillin in the face of oxacillin injury. This form of penicillin-induced liver injury occurs only with high dose therapy that is likely due to direct hepatotoxicity.

Drug Information

Used to treat bacterial infection by susceptible microorganisms.

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.

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

Bioavailability is 50–70% following oral administration.

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.

0.75–1 hour

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.

Floxacillin

Flucloxacillin Use and Manufacturing

Antibacterial.

Computed Properties

Molecular Weight:453.9
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:453.0561477
Monoisotopic Mass:453.0561477
Topological Polar Surface Area:138
Heavy Atom Count:30
Complexity:758
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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