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Revision as of 14:13, 31 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 01:41, 29 March 2024 edit undoSteel1943 (talk | contribs)Autopatrolled, Extended confirmed users, Page movers, Pending changes reviewers, Rollbackers, Template editors197,068 editsm →Available forms: formatting fix(es), replaced: ,''' → ''',Tag: AWB 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 458298378
| Watchedfields = changed
⚫ | IUPAC_name = (2''S'',5''R'',6''R'')-6-{amino}-3,3-dimethyl-7-oxo-4-thia-<br />1-azabicycloheptane-2-carboxylic acid
⚫ | verifiedrevid = 443636428
⚫ | IUPAC_name = (2''S'',5''R'',6''R'')-6-{amino}-3,3-dimethyl-7-oxo-4-thia-<br>1-azabicycloheptane-2-carboxylic acid
| image = Dicloxacillin.svg | image = Dicloxacillin.svg
| image2 = Dicloxacillin-based-on-xtal-3D-bs-17.png

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
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| legal_US = Rx-only | legal_US = Rx-only
| routes_of_administration = Oral | routes_of_administration = Oral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 60 to 80% | bioavailability = 60 to 80%
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| elimination_half-life = 0.7 hours | elimination_half-life = 0.7 hours
| excretion = ] and biliary | excretion = ] and biliary

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3116-76-5 | CAS_number = 3116-76-5
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 893 | ChEMBL = 893

<!--Chemical data--> <!--Chemical data-->
| C=19 | H=17 | Cl=2 | N=3 | O=5 | S=1 | C=19 | H=17 | Cl=2 | N=3 | O=5 | S=1
⚫ | SMILES = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1c(Cl)cccc1Cl)C)4SC3(C)C
| molecular_weight = 470.327 g/]
⚫ | smiles = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1c(Cl)cccc1Cl)C)4SC3(C)C
| InChI = 1/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
| InChIKey = YFAGHNZHGGCZAX-JKIFEVAIBY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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| StdInChIKey = YFAGHNZHGGCZAX-JKIFEVAISA-N | StdInChIKey = YFAGHNZHGGCZAX-JKIFEVAISA-N
}} }}
⚫ '''Dicloxacillin''' is a ] ] of the ] class.<ref name=":0" /> It is used to treat infections caused by susceptible (non-resistant) ].<ref name=":0">Product Information: DICLOXACILLIN SODIUM-dicloxacillin sodium capsule. Teva Pharmaceuticals USA Inc, Revised 8/2015</ref> It is active against ]-producing organisms such as '']'', which would otherwise be resistant to most ]s. Dicloxacillin is available under a variety of trade names including Diclocil (]).<ref>{{cite journal | vauthors = 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 = Annals of Clinical Microbiology and Antimicrobials | volume = 5 | pages = 25 | date = October 2006 | pmid = 17034644 | pmc = 1617116 | doi = 10.1186/1476-0711-5-25 | doi-access = free }}</ref>


<!-- Society and culture -->
⚫ '''Dicloxacillin''' (]) is a ] ] of the ] class. It is used to treat infections caused by susceptible ] ]. It is active against ]-producing organisms such as '']'',<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 ]s. It is very similar to ] and these two agents are considered interchangeable. Dicloxacillin is available under a variety of trade names including '''Diclocil''' (]).
It was patented in 1961 and approved for medical use in 1968.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=491 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA491 }}</ref> It is available as a ].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref>


==Mode of action== ==Medical uses==
Dicloxacillin is used to treat mild-to-moderate staphylococcal infections.<ref name="rossi">{{cite book | title = Dicloxacillin | url = https://www.ncbi.nlm.nih.gov/books/NBK548106/ | work = LiverTox: Clinical and Research Information on Drug-Induced Liver Injury | location = Bethesda (MD) | publisher = National Institute of Diabetes and Digestive and Kidney Diseases | date = 2012 | pmid = 31643436 }}</ref> 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.<ref name="rossi" />
⚫ {{main|Beta-lactam antibiotic}}


⚫ Dicloxacillin is similar in ], antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable.<ref name=":1">{{cite book | veditors = Rossi S | title = Australian Medicines Handbook | date = 2006 | location = Adelaide | publisher = Australian Medicines Handbook }}</ref> It is believed to have lower incidence of severe hepatic ] than flucloxacillin, but a higher incidence of renal adverse effects.<ref name=":1" />
⚫ Like other β-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial ]s. It inhibits cross-linkage between the linear ] polymer chains that make up a major component of the cell wall of ] bacteria.


⚫ Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:<ref name=":1" />
⚫ ==Medicinal chemistry==
⚫ Dicloxacillin is insensitive to ] (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the ] group on the side-chain of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side-chain ]. Thus, it is able to bind to ]s (PBPs) and inhibit ] crosslinking, but is not bound by or inactivated by β-lactamases.

==Clinical use==
Dicloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to ] routes. However, like ], it is less potent than ] against non-β-lactamase-producing ] bacteria.

⚫ Dicloxacillin has similar ], antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable. It is believed to have lower incidence of severe hepatic ] than flucloxacillin, but a higher incidence of renal adverse effects. (Rossi, 2006)

⚫ ===Available forms===
Dicloxacillin is commercially available as the sodium salt '''dicloxacillin sodium''' in ] (250 or 500 ]) and injections (powder for reconstitution, 500 and 1000 mg per vial).

===Indications===
⚫ Dicloxacillin is indicated for the treatment of infections caused by susceptible bacteria. Specific approved indications include: (Rossi, 2006)
*] and ] – including ], ], ], ]s, ], and ] *] and ] – including ], ], ], ]s, ], and ]
*] (adjunct) *] (adjunct)
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*Surgical ] *Surgical ]


⚫ ===Available forms===
===Precautions/contraindications===
Dicloxacillin is commercially available as the sodium salt, '''dicloxacillin sodium''', in ] and as a powder for reconstitution.<ref name=":0" /><ref>{{cite web | title = Dicloxacillin | work = MedlinePlus Drug Information | url = https://medlineplus.gov/druginfo/meds/a685017.html | publisher = U.S. National Library of Medicine, Department of Health and Human Services, National Institutes of Health }}</ref>
Dicloxacillin is contraindicated in those with a previous history of allergy to ]s, ]s or ]s. It should also not be used in the eye, or those with a history of ] associated with the use of dicloxacillin or flucloxacillin.


==Contraindications==
It should be used with caution in the elderly; patients with renal impairment, where a reduced dose is required; and those with hepatic impairment, due to the risk of cholestatic hepatitis. (Rossi, 2006)
Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/] reaction) to any penicillins.<ref name=":0" /><ref>{{cite web | work = DailyMed | title = DICLOXACILLIN SODIUM- dicloxacillin sodium capsule | url = https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=65c3e99b-ec77-416c-ad70-596d6f0a9c31 | publisher = National Institutes of Health, U.S. National Library of Medicine, Health & Human Services }}</ref>


==Adverse effects== ==Adverse effects==
Common ]s (ADRs) associated with the use of dicloxacillin include: ], ], ], ], ] and ] at injection site, ] (including ]), ], and transient increases in liver enzymes and bilirubin. (Rossi, 2006) Common ]s (ADRs) associated with the use of dicloxacillin include: ], ], ], ], ] and ] at injection site, ] (including ]), ], and transient increases in liver enzymes and bilirubin.<ref name=":1" />


On rare occasions, ] (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. (Joint Formulary Committee, 2005; Rossi, 2006) On rare occasions, ] (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.<ref name=":1" />

It should be used with caution and monitored in the elderly, particularly with intravenous administration, due to a risk of ].<ref name=":0" />

Dicloxacillin can also lower the effectiveness of birth control pills and pass into breast milk.<ref>{{cite web|url=https://www.everydayhealth.com/drugs/dicloxacillin|title=Dicloxacillin - Side Effects, Dosage, Interactions - Drugs - Everyday Health|website=EverydayHealth.com|date=23 June 2020 }}</ref>

=== Interactions ===
Dicloxacillin has potential interactions with following drugs:
* Warfarin<ref>{{cite journal | vauthors = Lacey CS | title = Interaction of dicloxacillin with warfarin | journal = The Annals of Pharmacotherapy | volume = 38 | issue = 5 | pages = 898 | date = May 2004 | pmid = 15054148 | doi = 10.1345/aph.1d484 | s2cid = 19182647 }}</ref>
* Methotrexate<ref>{{cite journal | vauthors = Ronchera CL, Hernández T, Peris JE, Torres F, Granero L, Jiménez NV, Plá JM | title = Pharmacokinetic interaction between high-dose methotrexate and amoxycillin | journal = Therapeutic Drug Monitoring | volume = 15 | issue = 5 | pages = 375–9 | date = October 1993 | pmid = 8249043 | doi = 10.1097/00007691-199310000-00004 | s2cid = 28111642 }}</ref>
* Tetracyclines<ref>{{cite journal | vauthors = Moellering RC | title = Rationale for use of antimicrobial combinations | journal = The American Journal of Medicine | volume = 75 | issue = 2A | pages = 4–8 | date = August 1983 | pmid = 6351605 | doi = 10.1016/0002-9343(83)90088-8 }}</ref>


==Resistance== ==Resistance==
Despite dicloxacillin's being insensitive to beta-lactamses, some organisms have developed resistance to it and other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms include ] (MRSA). Despite dicloxacillin being insensitive to beta-lactamases, some organisms have developed resistance to other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms include ] (MRSA).<ref>{{cite journal | vauthors = Rosdahl VT, Frimodt-Møller N, Bentzon MW | title = Resistance to dicloxacillin, methicillin and oxacillin in methicillin-susceptible and methicillin-resistant Staphylococcus aureus detected by dilution and diffusion methods | journal = APMIS | volume = 97 | issue = 8 | pages = 715–22 | date = August 1989 | pmid = 2669854 | doi = 10.1111/j.1699-0463.1989.tb00467.x | s2cid = 29646870 }}</ref>{{Better source|reason=This source explicitly says all MRSA strains they tested were susceptible to dicloxacillin. MRSA by itself is not relevant to this article. We need a source about dicloxacillin resistance.|date=October 2017}}


==See also== ==Mechanism of action==
⚫ {{main|β-Lactam antibiotic}}

⚫ Like other β-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial ]s. It inhibits cross-linkage between the linear ] polymer chains that make up a major component of the cell wall of ] bacteria.{{cn|date=March 2023}}

⚫ ==Medicinal chemistry==
⚫ Dicloxacillin is insensitive to ] (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the ] group on the side chain of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side-chain ]. Thus, it is able to bind to ]s (PBPs) and inhibit ] crosslinking, but is not bound by or inactivated by β-lactamase{{cn|date=March 2023}}

== See also ==
*] *]
*] *]
*] (formerly ], now ])


==References== == References ==
{{reflist}}
<references/>
*Rossi S, editor. ] 2006. Adelaide: Australian Medicines Handbook; 2006.


{{PenicillinAntiBiotics}} {{PenicillinAntiBiotics}}
{{Xenobiotic-sensing receptor modulators}}


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