| Revision as of 13:52, 19 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoB← Previous edit |
Latest revision as of 12:14, 9 August 2023 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,518 edits consistent citation formatting |
| (72 intermediate revisions by 49 users not shown) |
| Line 1: |
Line 1: |
|
|
{{short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 408782041 |
|
|
|
| Watchedfields = changed |
|
|IUPAC_name=(2''S'',5''R'',6''R'')-3,3-dimethyl-6--7-oxo-4-thia-1-<br>azabicycloheptane-2-carboxylic acid |
|
|
|
| verifiedrevid = 408783354 |
|
|image=Oxacillin skeletal.svg |
|
|
|
| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-6--7-oxo-4-thia-1-<br>azabicycloheptane-2-carboxylic acid |
|
|StdUNII_Ref = {{fdacite|correct|FDA}}= {{fdacite|correct|FDA}}= {{fdacite|correct|FDA}} |
|
|
|
| image = Oxacillin skeletal.svg |
|
|
| image2 = Oxacillin-based-on-xtal-3D-bs-17.png |
|
|
<!--Clinical data--> |
|
|
| tradename = Bactocill |
|
|
| Drugs.com = {{drugs.com|monograph|bactocill}} |
|
|
| MedlinePlus = a685020 |
|
|
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
|
| pregnancy_US = <!-- A / B / C / D / X --> |
|
|
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
|
|
| legal_UK = <!-- GSL / P / POM / CD --> |
|
|
| legal_US = <!-- OTC / Rx-only --> |
|
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
|
| CAS_number = 66-79-5 |
|
|
| ATC_prefix = J01 |
|
|
| ATC_suffix = CF04 |
|
|
| ATC_supplemental = {{ATCvet|J51|CF04}} |
|
|
| PubChem = 6196 |
|
|
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
|
|
| DrugBank = DB00713 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 5961 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = UH95VD7V76 |
|
| UNII = UH95VD7V76 |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
|
| ChEMBL = 891 |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChI = 1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1 |
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChIKey = LQOLIRLGBULYKD-JKIFEVAISA-N |
|
|
| CAS_number=66-79-5 |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
|ATC_prefix=J01 |
|
|
|ATC_suffix=CF04 |
|
|
|ATC_supplemental={{ATCvet|J51|CF04}} |
|
|
|PubChem = 6098 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
| ChemSpiderID=5873 |
|
|
|DrugBank= |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D08307 |
|
| KEGG = D08307 |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|C=19|H=19|N=3|O=5|S=1 |
|
|
|
| ChEBI = 7809 |
|
|molecular_weight=401.436 g/mol |
|
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|boiling_point = 686.8 |
|
|
|
| ChEMBL = 819 |
|
|bioavailability= |
|
|
|
<!--Chemical data--> |
|
|density = 1.49 |
|
|
|
| C=19 | H=19 | N=3 | O=5 | S=1 |
|
|protein_bound= |
|
|
|
| smiles = 12SC(C)(C)(N1C(=O)2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O |
|
|metabolism= |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|elimination_half-life= |
|
|
|
| StdInChI = 1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1 |
|
|excretion= |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|pregnancy_AU=<!-- A / B1 / B2 / B3 / C / D / X --> |
|
|
|
| StdInChIKey = UWYHMGVUTGAWSP-JKIFEVAISA-N |
|
|pregnancy_US=<!-- A / B / C / D / X --> |
|
|
|
| density = 1.49 |
|
|pregnancy_category= |
|
|
|
| boiling_point = 686.8 |
|
|legal_AU=<!-- Unscheduled / S2 / S4 / S8 --> |
|
|
|legal_UK=<!-- GSL / P / POM / CD --> |
|
|
|legal_US=<!-- OTC / Rx-only --> |
|
|
|legal_status= |
|
|
|routes_of_administration= |
|
|
|smiles = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1ccccc1Cl)C)4SC3(C)C |
|
|
}} |
|
}} |
|
|
|
|
|
'''Oxacillin sodium''' (trade name '''Bactocill''') is a ] ] of the ] class. |
|
'''Oxacillin''' (trade name '''Bactocill''') is a ] ] of the ] class developed by ].<ref name="Greenwood2008">{{cite book| vauthors = Greenwood D |title=Antimicrobial drugs: chronicle of a twentieth century medical triumph|url=https://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124|access-date=18 November 2010|year=2008|publisher=Oxford University Press US|isbn=978-0-19-953484-5|pages=124–}}</ref> |
|
|
|
|
|
|
<!-- Society and culture --> |
|
It was developed by ].<ref name="Greenwood2008">{{cite book|author=David Greenwood|title=Antimicrobial drugs: chronicle of a twentieth century medical triumph|url=http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124|accessdate=18 November 2010|year=2008|publisher=Oxford University Press US|isbn=9780199534845|pages=124–}}</ref> |
|
|
|
It was patented in 1960 and approved for medical use in 1962.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=490 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA490 |language=en}}</ref> |
|
|
|
|
|
==Uses== |
|
==Medical uses== |
|
|
|
|
Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by '']'', it is widely used clinically in the US to treat penicillin-resistant '']''. However, resistant strains called ] (MRSA/ORSA) are highly prevalent in the U.S. and the U.K. |
|
|
|
|
|
|
|
Oxacillin is a penicillinase-resistant ]. It is similar to ], and has replaced methicillin in clinical use. Other related compounds are ], ], ], and ]. Since it is resistant to penicillinase enzymes, such as that produced by '']'', it is widely used clinically in the US to treat penicillin-resistant '']''. However, with the introduction and widespread use of both oxacillin and methicillin, ] strains called ] and oxacillin-resistant ''Staphylococcus aureus'' (MRSA/ORSA) have become increasingly prevalent worldwide. MRSA/ORSA can be treated with ] or other new antibiotics.{{cn|date=March 2023}} |
|
==References== |
|
|
{{Reflist}} |
|
|
|
|
|
|
|
==Contraindications== |
|
{{Cell wall disruptive antibiotics}} |
|
|
|
The use of oxacillin is contraindicated in individuals that have experienced a hypersensitivity reaction to any medication in the penicillin family of antibiotics.<ref name="Bactocill">Drugs.com: </ref> Cross-allergenicity has been documented in individuals taking oxacillin that experienced a previous hypersensitivity reaction when given ] and ].<ref>Apothecon. Oxacillin sodium for injection for intramuscular or intravenous injection prescribing information. Princeton, NJ; 2001 Jan.</ref><ref>{{cite journal | vauthors = Erffmeyer JE | title = Adverse reactions to penicillin. Part I | journal = Annals of Allergy | volume = 47 | issue = 4 | pages = 288–93 | date = October 1981 | pmid = 6171185 }}</ref> |
|
|
|
|
|
|
==Adverse effects== |
|
] |
|
|
|
{{further|Penicillin drug reaction}} |
|
] |
|
|
|
Commonly reported adverse effects associated with the use of oxacillin include skin rash, diarrhea, nausea, vomiting, hematuria, agranulocytosis, eosinophilia, leukopenia, neutropenia, thrombocytopenia, hepatotoxicity, acute interstitial nephritis, and fever. High doses of oxacillin have been reported to cause renal, hepatic, and nervous system toxicity. Common to all members of the penicillin class of drugs, oxacillin may cause acute or delayed hypersensitivity reactions. As an injection, oxacillin may cause injection site reactions, which may be characterized by redness, swelling, and itching.<ref name="Bactocill"/> |
|
|
|
|
|
|
==Pharmacology== |
|
|
|
|
|
|
===Mechanism of Action=== |
|
{{Antibiotic-stub}} |
|
|
|
Oxacillin, through its β-lactam ring, covalently binds to penicillin-binding proteins, which are enzymes involved in the synthesis of the bacterial cell wall. This binding interaction interferes with the transpeptidation reaction and inhibits the synthesis of peptidoglycan, a prominent component of the cell wall. By decreasing the integrity of the bacterial cell wall, it is thought that oxacillin and other penicillins kill actively growing bacteria through cell autolysis.<ref name="Basic and Clinical Pharmacology">{{cite book| vauthors = Katzung B, Trevor A |title=Basic and Clinical Pharmacology|date=2014|publisher=Mcgraw-Hill|location=New York|isbn=978-0071825054|edition=13TH|url=http://accesspharmacy.mhmedical.com/book.aspx?bookid=1193|access-date=3 November 2017}}</ref> |
|
|
|
|
|
|
==Chemistry== |
|
] |
|
|
|
As with other members of the penicillin family, the chemical structure of oxacillin features a 6-aminopenicillanic acid nucleus with a substituent attached to the amino group. The 6-aminopenicillanic acid nucleus consists of a thiazolidine ring attached to a β-lactam ring, which is the active moiety responsible for the antibacterial activity of the penicillin family. The substituent present on oxacillin is thought to impart resistance to degradation via bacterial β-lactamases.<ref name="Basic and Clinical Pharmacology"/> |
|
] |
|
|
|
|
|
] |
|
|
|
==History== |
|
] |
|
|
|
Oxacillin, a derivative of ], was first synthesized in the early 1960s as part of a research initiative led by ] and John Naylor of ], in consort with ]. Members of the ] penicillin family, which includes ], ], and oxacillin, were synthesized to counter the increasing prevalence of infections caused by penicillin-resistant '']''. While methicillin could only be administered via injection, the isoxazolyl penicillins, including oxacillin, could be given orally or by injection. Following the synthesis of cloxacillin and oxacillin, Beecham retained the right to commercially develop cloxacillin in the United Kingdom while Bristol-Myers was given the marketing rights for oxacillin in the United States.<ref name="Greenwood2008"/> |
|
] |
|
|
|
|
|
] |
|
|
|
==Society and Culture== |
|
] |
|
|
|
===FDA Approval History<ref name="Bactocill"/>=== |
|
] |
|
|
|
*April 8, 1971: Oxacillin Sodium Injectable |
|
] |
|
|
|
**Applicant: Sandoz |
|
|
*July 27, 1973: Bactocill Capsule |
|
|
**Applicant: GlaxoSmithKline |
|
|
*March 10, 1980: Oxacillin Sodium Capsule |
|
|
**Applicant: Ani Pharms Inc |
|
|
*May 15, 1980: Oxacillin Sodium for Solution |
|
|
**Applicant: TEVA |
|
|
*June 2, 1981: Bactocill for Solution |
|
|
**Applicant: GlaxoSmithKline |
|
|
*December 23, 1986: Oxacillin Sodium Powder |
|
|
**Applicant: Sandoz |
|
|
*September 29, 1988: Oxacillin Sodium Injectable |
|
|
**Applicant: Watson Labs Inc |
|
|
*October 26, 1988: Oxacillin Sodium Injectable |
|
|
**Applicant: Watson Labs Inc |
|
|
*October 26, 1989: Bactocill in Plastic Container Injectable |
|
|
**Applicant: Baxter Healthcare |
|
|
*March 30, 2012: Oxacillin Sodium Injectable |
|
|
**Applicant: Sagent Pharms |
|
|
*January 18, 2013: Oxacillin Sodium Injectable |
|
|
**Applicant: Aurobindo Pharma LTD |
|
|
*August 25, 2014: Oxacillin Sodium Injectable |
|
|
**Applicant: Mylan Labs LTD |
|
|
*December 11, 2015: Oxacillin Sodium Injectable |
|
|
**Applicant: Hospira Inc |
|
|
*July 31, 2017: Oxacillin Sodium Injectable |
|
|
**Applicant: Wockhardt Bio/Ag |
|
|
|
|
|
===Pricing=== |
|
|
The ] (AWP) for oxacillin products are provided as follows. The prices listed below are intended to serve as reference values and do not represent the pricing determined by any single manufacturer or entity.<ref name="Bactocill"/> |
|
|
*Bactocill in Dextrose Intravenous |
|
|
**1 g/50 mL: $20.37 |
|
|
**2 g/50 mL: $32.48 |
|
|
*Oxacillin Sodium Injection |
|
|
**1 g: $17.52 |
|
|
**2 g: $33.99 |
|
|
**10 g: $138.77 |
|
|
|
|
|
== References == |
|
|
|
|
|
* |
|
|
|
|
|
{{Reflist}} |
|
|
|
|
|
{{Cell wall disruptive antibiotics}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |