Dicloxacillin

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Dicloxacillin
Dicloxacillin.svg
Systematic (IUPAC) name
(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
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a685017
Pregnancy
category
  • AU: B2
  • US: B (No risk in non-human studies)
Legal status
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability 60 to 80%
Protein binding 98%
Metabolism Hepatic
Biological half-life 0.7 hours
Excretion Renal and biliary
Identifiers
CAS Number 3116-76-5 YesY
ATC code J01CF01 (WHO) QJ51CF01 (WHO)
PubChem CID: 18381
DrugBank DB00485 YesY
ChemSpider 17358 YesY
UNII COF19H7WBK YesY
KEGG D02348 YesY
ChEBI CHEBI:4511 YesY
ChEMBL CHEMBL893 YesY
Chemical data
Formula C19H17Cl2N3O5S
Molecular mass 470.327 g/mol
  • 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 YesY
  • Key:YFAGHNZHGGCZAX-JKIFEVAISA-N YesY
  (verify)

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

Medical uses

Dicloxacillin is used to treat mild-to-moderate staphylococcal infections.[3] To decrease the development of resistance, dicloxacillin is recommended to treat infections that are suspected or proven to be caused by beta-lactamase-producing bacteria.[3]

Dicloxacillin has similar pharmacokinetics, antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable.[4] It is believed to have lower incidence of severe hepatic adverse effects than flucloxacillin, but a higher incidence of renal adverse effects.[4]

Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:[4]

Available forms

Dicloxacillin is commercially available as the sodium salt, dicloxacillin sodium, in capsules and as a powder for reconstitution.[1][5]

Contraindications

Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.[1][6]

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.[4]

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 over 55 years old, females, and those with treatment longer than 2 weeks.[4]

It should be used with caution and monitored in the elderly, particularly with intravenous administration, due to a risk of thrombophlebitis.[1]

Interactions

Dicloxacillin has potential interactions with following drugs:

  • Warfarin[7]
  • Methotrexate[8]
  • Tetracyclines[9]

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) and methicillin-susceptible Staphylococcus aureus (MSSA).[10]

Mechanism of action

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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. ↑ 1.0 1.1 1.2 1.3 1.4 Product Information: DICLOXACILLIN SODIUM-dicloxacillin sodium capsule. Teva Pharmaceuticals USA Inc, Revised 8/2015
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 "Dicloxacillin". livertox.nih.gov. Retrieved 2015-11-05.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006
  5. ↑ "Dicloxacillin: MedlinePlus Drug Information". www.nlm.nih.gov. Retrieved 2015-11-05.
  6. ↑ "DailyMed - DICLOXACILLIN SODIUM- dicloxacillin sodium capsule". dailymed.nlm.nih.gov. Retrieved 2015-11-05.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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