| 词条 | Dicloxacillin |
| 释义 |
| verifiedrevid = 458298378 | IUPAC_name = (2S,5R,6R)-6[3-(2,6-dichlorophenyl)-5-methyl- oxazole-4-carbonyl]amino3,3-dimethyl-7-oxo-4-thia- 1-azabicyclo[3.2.0]heptane-2-carboxylic acid | image = Dicloxacillin.svg | tradename = | Drugs.com = {{drugs.com|monograph|dicloxacillin-sodium}} | MedlinePlus = a685017 | pregnancy_AU = B2 | pregnancy_US = B | legal_AU = S4 | legal_US = Rx-only | routes_of_administration = Oral | bioavailability = 60 to 80% | protein_bound = 98% | metabolism = Hepatic | elimination_half-life = 0.7 hours | excretion = Renal and biliary | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 3116-76-5 | ATC_prefix = J01 | ATC_suffix = CF01 | ATC_supplemental = {{ATCvet|J51|CF01}} | PubChem = 18381 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00485 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 17358 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = COF19H7WBK | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D02348 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 4511 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 893 | C=19 | H=17 | Cl=2 | N=3 | O=5 | S=1 | molecular_weight = 470.327 g/mol | SMILES = O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(Cl)cccc1Cl)C)[C@H]4SC3(C)C | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YFAGHNZHGGCZAX-JKIFEVAISA-N }}Dicloxacillin 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] It was patented in 1961 and approved for medical use in 1968.[3] Medical usesDicloxacillin is used to treat mild-to-moderate staphylococcal infections.[4] 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.[4] Dicloxacillin is similar in pharmacokinetics, antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable.[5] It is believed to have lower incidence of severe hepatic adverse effects than flucloxacillin, but a higher incidence of renal adverse effects.[5] Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:[5]
Available formsDicloxacillin is commercially available as the sodium salt, dicloxacillin sodium, in capsules and as a powder for reconstitution.[1][6] ContraindicationsDicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.[1][7] Adverse effectsCommon 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.[5] 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.[5] It should be used with caution and monitored in the elderly, particularly with intravenous administration, due to a risk of thrombophlebitis.[1] Dicloxacillin can also lower the effectiveness of birth control pills and pass into breast milk. [8]. InteractionsDicloxacillin has potential interactions with following drugs:
ResistanceDespite dicloxacillin being insensitive to beta-lactamases, some organisms have developed resistance to other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms include methicillin-resistant Staphylococcus aureus (MRSA).[12]{{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}} Mechanism of action{{main|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 chemistryDicloxacillin 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-lactamase See also
References1. ^1 2 3 4 Product Information: DICLOXACILLIN SODIUM-dicloxacillin sodium capsule. Teva Pharmaceuticals USA Inc, Revised 8/2015 {{PenicillinAntiBiotics}}{{Xenobiotic-sensing receptor modulators}}2. ^{{cite journal|last1=Miranda-Novales|first1=G|last2=Leaños-Miranda|first2=BE|last3=Vilchis-Pérez|first3=M|last4=Solórzano-Santos|first4=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|date=12 October 2006|volume=5|pages=25|pmid=17034644|doi=10.1186/1476-0711-5-25|pmc=1617116}} 3. ^{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=491 |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA491 |language=en}} 4. ^1 "Dicloxacillin". livertox.nih.gov. Retrieved 2015-11-05. 5. ^1 2 3 4 Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006 6. ^"Dicloxacillin: MedlinePlus Drug Information". www.nlm.nih.gov. Retrieved 2015-11-05. 7. ^"DailyMed - DICLOXACILLIN SODIUM- dicloxacillin sodium capsule". dailymed.nlm.nih.gov. Retrieved 2015-11-05. 8. ^{{cite web|url=https://www.everydayhealth.com/drugs/dicloxacillin|title=Dicloxacillin - Side Effects, Dosage, Interactions - Drugs - Everyday Health|author=|date=|website=EverydayHealth.com}} 9. ^{{cite journal|last1=Lacey|first1=CS|title=Interaction of dicloxacillin with warfarin.|journal=The Annals of Pharmacotherapy|date=May 2004|volume=38|issue=5|pages=898|pmid=15054148|doi=10.1345/aph.1d484}} 10. ^{{cite journal|last1=Ronchera|first1=CL|last2=Hernández|first2=T|last3=Peris|first3=JE|last4=Torres|first4=F|last5=Granero|first5=L|last6=Jiménez|first6=NV|last7=Plá|first7=JM|title=Pharmacokinetic interaction between high-dose methotrexate and amoxycillin.|journal=Therapeutic drug monitoring|date=October 1993|volume=15|issue=5|pages=375–9|pmid=8249043|doi=10.1097/00007691-199310000-00004}} 11. ^{{cite journal|last1=Moellering RC|first1=Jr|title=Rationale for use of antimicrobial combinations.|journal=The American Journal of Medicine|date=29 August 1983|volume=75|issue=2A|pages=4–8|pmid=6351605|doi=10.1016/0002-9343(83)90088-8}} 12. ^{{cite journal|last1=Rosdahl|first1=VT|last2=Frimodt-Møller|first2=N|last3=Bentzon|first3=MW|title=Resistance to dicloxacillin, methicillin and oxacillin in methicillin-susceptible and methicillin-resistant Staphylococcus aureus detected by dilution and diffusion methods.|journal=APMIS : acta pathologica, microbiologica, et immunologica Scandinavica|date=August 1989|volume=97|issue=8|pages=715–22|pmid=2669854}} 4 : Penicillins|Enantiopure drugs|Isoxazoles|Chloroarenes |
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