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'''Dicloxacillin''' ([[International Nonproprietary Name|INN]]) is a [[narrow-spectrum antibiotic|narrow-spectrum]] [[β-Lactam antibiotic]] of the [[penicillin]] class. It is used to treat infections caused by susceptible [[Gram-positive]] [[bacteria]]. It is active against [[beta-lactamase]]-producing organisms such as ''[[Staphylococcus aureus]]'',<ref name="pmid17034644">{{cite journal |author=Miranda-Novales G, Leaños-Miranda BE, Vilchis-Pérez M, Solórzano-Santos F |title=''In vitro'' activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant ''Staphylococcus'' spp. strains |journal=Ann. Clin. Microbiol. Antimicrob. |volume=5 |issue= |pages=25 |year=2006 |pmid=17034644 |pmc=1617116 |doi=10.1186/1476-0711-5-25 |url=http://www.ann-clinmicrob.com/content/5//25}}</ref> which would otherwise be resistant to most [[penicillin]]s. It is very similar to [[flucloxacillin]] and these two agents are considered interchangeable. Dicloxacillin is available under a variety of trade names including Diclocil ([[Bristol-Myers Squibb|BMS]]).
'''Dicloxacillin''' (INN) is a narrow-spectrum β-Lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria.<ref name=":0">Product Information: DICLOXACILLIN SODIUM-dicloxacillin sodium capsule. Teva Pharmaceuticals USA Inc, Revised 8/2015</ref> It is active against beta-lactamase-producing organisms such as ''Staphylococcus aureus'',<ref>Miranda-Novales G, Leaños-Miranda BE, Vilchis-Pérez M, Solórzano-Santos F (2006). "''In vitro'' activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant ''Staphylococcus'' spp. strains". ''Ann. Clin. Microbiol. Antimicrob.'' '''5''': 25. doi:10.1186/1476-0711-5-25. PMC 1617116.<nowiki>PMID 17034644</nowiki>.</ref> which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).


==Medical uses==
==Medical uses==
Dicloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to [[parenteral]] routes. However, like [[methicillin]], it is less potent than [[benzylpenicillin]] against non-β-lactamase-producing [[Gram-positive]] bacteria.
Dicloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to [[parenteral]] routes. However, like [[methicillin]], it is less potent than [[benzylpenicillin]] against non-β-lactamase-producing [[Gram-positive]] bacteria.


Dicloxacillin has similar [[pharmacokinetics]], antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable. It is believed to have lower incidence of severe hepatic [[adverse effect (medicine)|adverse effects]] than flucloxacillin, but a higher incidence of renal adverse effects.<ref name="rossi" />
Dicloxacillin has similar [[pharmacokinetics]], antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable. It is believed to have lower incidence of severe hepatic [[adverse effect (medicine)|adverse effects]] than flucloxacillin, but a higher incidence of renal adverse effects.<ref name="rossi">Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006</ref>


Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:<ref name="rossi" />
Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:<ref name="rossi" />
Line 64: Line 64:


===Available forms===
===Available forms===
Dicloxacillin is commercially available as the sodium salt '''dicloxacillin sodium''' in [[Capsule (pharmacy)|capsules]] and injections (powder for reconstitution).
Dicloxacillin is commercially available as the sodium salt '''dicloxacillin sodium''' in capsules and as a powder for reconstitution.<ref name=":0" />
its also available as name of novaclox.


==Contraindications==
==Contraindications==
Dicloxacillin is contraindicated in those with a previous history of allergy to [[penicillin]]s, [[cephalosporin]]s or [[carbapenem]]s. It should also not be used in the eye, or those with a history of [[cholestasis|cholestatic hepatitis]] associated with the use of dicloxacillin or flucloxacillin.
Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.<ref name=":0" /> It should also not be used in the eye, or those with a history of cholestatic hepatitis associated with the use of dicloxacillin or flucloxacillin.


It should be used with caution in the elderly; renal impairment does not need dose adjustment<Bennett WM, Aronoff GR, Golper TA et al: Drug Prescribing in Renal Failure. American College of Physicians, 3rd ed, Philadelphia, PA, 1994.> while those with hepatic impairment do, due to the risk of cholestatic hepatitis.<ref name=rossi>Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006</ref>
It should be used with caution in the elderly; renal impairment does not need dose adjustment, while those with hepatic impairment do, due to the risk of cholestatic hepatitis.<ref name="rossi" /><ref>Bennett WM, Aronoff GR, Golper TA et al: Drug Prescribing in Renal Failure. American College of Physicians, 3rd ed, Philadelphia, PA, 1994</ref>

Dicloxacillin is Pregnancy Category B-with no conclusive studies about its fetal effects; however, penicillins do show up in breast milk and caution should be taken in nursing women.<ref name=":0" />


==Adverse effects==
==Adverse effects==

Revision as of 01:04, 4 November 2015

Dicloxacillin
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa685017
Pregnancy
category
  • AU: B2
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60 to 80%
Protein binding98%
MetabolismHepatic
Elimination half-life0.7 hours
ExcretionRenal and biliary
Identifiers
  • (2S,5R,6R)-6-{[3-(2,6-dichlorophenyl)-5-methyl-
    oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-
    1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.535 Edit this at Wikidata
Chemical and physical data
FormulaC19H17Cl2N3O5S
Molar mass470.327 g/mol g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(Cl)cccc1Cl)C)[C@H]4SC3(C)C
  • InChI=1S/C19H17Cl2N3O5S/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 checkY
  • Key:YFAGHNZHGGCZAX-JKIFEVAISA-N checkY
  (verify)

Dicloxacillin (INN) is a narrow-spectrum β-Lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria.[1] It is active against beta-lactamase-producing organisms such as Staphylococcus aureus,[2] which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

Medical uses

Dicloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to parenteral routes. However, like methicillin, it is less potent than benzylpenicillin against non-β-lactamase-producing Gram-positive bacteria.

Dicloxacillin has similar pharmacokinetics, antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable. It is believed to have lower incidence of severe hepatic adverse effects than flucloxacillin, but a higher incidence of renal adverse effects.[3]

Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:[3]

Available forms

Dicloxacillin is commercially available as the sodium salt dicloxacillin sodium in capsules and as a powder for reconstitution.[1]

Contraindications

Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.[1] It should also not be used in the eye, or those with a history of cholestatic hepatitis associated with the use of dicloxacillin or flucloxacillin.

It should be used with caution in the elderly; renal impairment does not need dose adjustment, while those with hepatic impairment do, due to the risk of cholestatic hepatitis.[3][4]

Dicloxacillin is Pregnancy Category B-with no conclusive studies about its fetal effects; however, penicillins do show up in breast milk and caution should be taken in nursing women.[1]

Adverse effects

Common adverse drug reactions (ADRs) associated with the use of dicloxacillin include: diarrhoea, nausea, rash, urticaria, pain and inflammation at injection site, superinfection (including candidiasis), allergy, and transient increases in liver enzymes and bilirubin.[3]

On rare occasions, cholestatic jaundice (also referred to as cholestatic hepatitis) has been associated with dicloxacillin therapy. The reaction may occur up to several weeks after treatment has stopped, and takes weeks to resolve. The estimated incidence is 1 in 15,000 exposures, and is more frequent in people >55 years, females, and those with treatment longer than 2 weeks.[3]

Resistance

Despite dicloxacillin's being insensitive to beta-lactamases, some organisms have developed resistance to it and other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms include methicillin-resistant Staphylococcus aureus (MRSA).

Mechanism of action

Main article: β-Lactam antibiotic

Like other β-Lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria.

Medicinal chemistry

Dicloxacillin is insensitive to beta-lactamase (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the isoxazolyl group on the side chain of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side-chain steric hindrance. Thus, it is able to bind to penicillin-binding proteins (PBPs) and inhibit peptidoglycan crosslinking, but is not bound by or inactivated by β-lactamases.

See also

References

  1. ^ a b c d Product Information: DICLOXACILLIN SODIUM-dicloxacillin sodium capsule. Teva Pharmaceuticals USA Inc, Revised 8/2015
  2. ^ Miranda-Novales G, Leaños-Miranda BE, Vilchis-Pérez M, Solórzano-Santos F (2006). "In vitro activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains". Ann. Clin. Microbiol. Antimicrob. 5: 25. doi:10.1186/1476-0711-5-25. PMC 1617116.PMID 17034644.
  3. ^ a b c d e Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006
  4. ^ Bennett WM, Aronoff GR, Golper TA et al: Drug Prescribing in Renal Failure. American College of Physicians, 3rd ed, Philadelphia, PA, 1994


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