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BE5ST/sandbox
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
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.[1] 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, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).[2]

Medical Uses

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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] 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.[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

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

Contraindications

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Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.[1][6] 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, particularly with intravenous administration, due to a risk of thrombophlebitis.[1]

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

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Common adverse drug reactions (ADRs) associated with the use of dicloxacillin include: diarrhea, 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 >55 years, females, and those with treatment longer than 2 weeks.[4]

Interactions

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Dicloxacillin has potential interactions with following drugs:

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

Resistance

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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

[edit]

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

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References

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  1. ^ a b c d e f 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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  3. ^ a b "Dicloxacillin". livertox.nih.gov. Retrieved 2015-11-05.
  4. ^ a b c d e 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. ^ Lacey, Christopher S. (2004-05-01). "Interaction of dicloxacillin with warfarin". Annals of Pharmacotherapy. 38 (5): 898. doi:10.1345/aph.1D484. ISSN 1060-0280. PMID 15054148. S2CID 19182647.
  8. ^ Ronchera, C. L.; Hernández, T.; Peris, J. E.; Torres, F.; Granero, L.; Jiménez, N. V.; Plá, J. M. (1993-10-01). "Pharmacokinetic interaction between high-dose methotrexate and amoxycillin". Therapeutic Drug Monitoring. 15 (5): 375–379. doi:10.1097/00007691-199310000-00004. ISSN 0163-4356. PMID 8249043. S2CID 28111642.
  9. ^ Moellering, R. C. (1983-08-29). "Rationale for use of antimicrobial combinations". The American Journal of Medicine. 75 (2A): 4–8. doi:10.1016/0002-9343(83)90088-8. ISSN 0002-9343. PMID 6351605.
  10. ^ Rosdahl, V. T.; Frimodt-Møller, N.; Bentzon, M. W. (1989-08-01). "Resistance to dicloxacillin, methicillin and oxacillin in methicillin-susceptible and methicillin-resistant Staphylococcus aureus detected by dilution and diffusion methods". APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica. 97 (8): 715–722. doi:10.1111/j.1699-0463.1989.tb00467.x. ISSN 0903-4641. PMID 2669854. S2CID 29646870.


Category:Beta-lactam antibiotics Category:Enantiopure drugs Category:Isoxazoles Category:Chloroarenes

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