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Revision as of 13:45, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 459474989 of page Torezolid for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 07:00, 1 November 2024 edit 2600:1014:b057:fe3e:2930:85c6:5637:f50 (talk) Added brand name manufacturer - MerckTags: Mobile edit Mobile web edit 
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{{Short description|Oxazolidinone-class antibiotic}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 459473288 | verifiedrevid = 470611892
| image = Tedizolid.svg
| IUPAC_name = (5''R'')-3-{3-fluoro-4-phenyl}-5-(hydroxymethyl)-1,3-oxazolidin-2-one
| image = Torezolid.svg | alt =


<!--Clinical data--> <!--Clinical data-->
| tradename = | pronounce =
| tradename = Sivextro
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| Drugs.com = {{drugs.com|monograph|tedizolid-phosphate}}
| pregnancy_US = <!-- A / B / C / D / X -->
| MedlinePlus = a614038
| DailyMedID = Tedizolid
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_category = | pregnancy_category =
| routes_of_administration = ], ]
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| ATC_prefix = J01
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| ATC_suffix = XX11
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = Investigational
| routes_of_administration =


<!--Pharmacokinetic data--> <!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| bioavailability =
| protein_bound = | legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Health Canada New Drug Authorizations: 2015 Highlights | website=] | date=4 May 2016 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2015-highlights.html | access-date=7 April 2024}}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment = <ref name="Sivextro FDA label" />
| legal_EU = Rx-only
| legal_EU_comment = <ref name="Sivextro EPAR" />
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 91%
| protein_bound = 70–90%
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life = 12 hours
| excretion = | excretion = Feces


<!--Identifiers--> <!--Identifiers-->
| index2_label = Phosphate
| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 856867-55-5
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = O7DRJ6R4DW
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 856866-72-3 --> | CAS_number = 856866-72-3
| PubChem =11234049
| ATC_prefix = none
| ATC_suffix =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H15FN6O3/c1-23-21-16(20-22-23)15-5-2-10(7-19-15)13-4-3-11(6-14(13)18)24-8-12(9-25)27-17(24)26/h2-7,12,25H,8-9H2,1H3/t12-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XFALPSLJIHVRKE-GFCCVEGCSA-N
| PubChem =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank = DB09042
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9409096 | ChemSpiderID = 9409096
Line 43: Line 64:
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D09685 | KEGG = D09685
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D09686
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 82717
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1257051 --> | ChEMBL = 1257051
| synonyms = TR-700, torezolid<ref name=Nov2011>{{cite news |url=http://www.signonsandiego.com/news/2011/oct/31/trius-grows-lead-antibiotic-moves-forward/ |title=Trius grows as lead antibiotic moves forward |date=31 Oct 2011 }}</ref>

<!--Chemical data-->
| IUPAC_name = (5''R'')-3-{3-fluoro-4-phenyl}-5-(hydroxymethyl)-1,3-oxazolidin-2-one
| C=17 | H=15 | F=1 | N=6 | O=3 | C=17 | H=15 | F=1 | N=6 | O=3
| molecular_weight = 370.338 g/mol
| smiles = O=C4O(CN4c3cc(F)c(c1ccc(nc1)c2nn(nn2)C)cc3)CO | smiles = O=C4O(CN4c3cc(F)c(c1ccc(nc1)c2nn(nn2)C)cc3)CO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H15FN6O3/c1-23-21-16(20-22-23)15-5-2-10(7-19-15)13-4-3-11(6-14(13)18)24-8-12(9-25)27-17(24)26/h2-7,12,25H,8-9H2,1H3/t12-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XFALPSLJIHVRKE-GFCCVEGCSA-N
}} }}

'''Tedizolid''', sold under the brand name '''Sivextro''' (by Merck) is an ]-class antibiotic. '''Tedizolid phosphate''' is a ] prodrug of the active compound tedizolid. It was developed by ], following acquisition of ] (originator: Dong-A Pharmaceuticals), and is marketed for the treatment of acute bacterial skin and skin structure infections (also known as ] (cSSSIs)).<ref>{{cite news |url=http://investors.cubist.com/Mobile/file.aspx?IID=4093793&FID=18531897 |title=Cubist Pharmaceuticals to Acquire Trius Therapeutics |date=July 2013 |access-date=2015-03-17 |archive-date=2015-04-02 |archive-url=https://web.archive.org/web/20150402125618/http://investors.cubist.com/Mobile/file.aspx?IID=4093793&FID=18531897 |url-status=dead }}</ref>{{Medical citation needed|date=April 2024}}

The most common side effects include nausea (feeling sick), headache, diarrhoea and vomiting.<ref name="Sivextro EPAR" /> These side effects were generally of mild or moderate severity.<ref name="Sivextro EPAR" />

Tedizolid was approved for medical use in the United States in June 2014,<ref name="FDA approval tablets" /><ref name="FDA approval injection" /> and for medical use in the European Union in March 2015.<ref name="Sivextro EPAR" />

== Medical uses ==
Tedizolid was approved by the U.S ] (FDA) on June 20, 2014, with the indication for the treatment of acute bacterial ]s (ABSSSI) caused by certain susceptible bacteria, including '']'' (including methicillin-resistant strains, ], and methicillin-susceptible strains), various '']'' species (''S. pyogenes'', ''S. agalactiae'', and ''S. anginosus'' group including ''S. anginosus'', ''S. intermedius'', and ''S. constellatus''), and '']''.<ref name="FDA approval tablets">{{cite web | title=Drug Approval Package: Sivextro (tedizolid phosphate) Tablets NDA #205435 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205435Orig1s000TOC.cfm | access-date=5 July 2020}}</ref><ref name="FDA approval injection">{{cite web | title=Drug Approval Package: Sivextro (tedizolid phosphate) Injection NDA #205436 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205436Orig1s000TOC.cfm | access-date=5 July 2020}}</ref><ref name ="FDA Approval">{{cite press release |url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm402174.htm |title=FDA approves Sivextro to treat skin infections |date=June 2014 |access-date=2019-12-16 |archive-url=https://web.archive.org/web/20170121233816/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm402174.htm |archive-date=2017-01-21 |url-status=dead }}</ref><ref name="Sivextro FDA label">{{cite web | title=Sivextro- tedizolid phosphate tablet, film coated Sivextro- tedizolid phosphate injection, powder, lyophilized, for solution | website=DailyMed | date=22 June 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=75672079-589f-451a-bdbf-eaebcfcc80a9 | access-date=24 October 2020}}</ref> Tedizolid is a second-generation ] derivative that is 4-to-16-fold more potent against staphylococci and enterococci compared to ].<ref>. Accessed 2015-03-16.</ref> The recommended dosage for treatment is 200&nbsp;mg once daily for a total duration of six days, either orally (with or without food) or through an intravenous injection (if patient is older than 18 years old).<ref name="Sivextro FDA label"/>

In the European Union tedizolid is indicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) in adults.<ref name="Sivextro EPAR">{{cite web | title=Sivextro EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/sivextro | access-date=5 July 2020}} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref>

==Mechanism of action==
Tedizolid phosphate (TR-701) is a ] activated by plasma or intestinal ] to tedizolid (TR-700) following administration of the drug either orally or intravenously.<ref name="Sivextro FDA label"/><ref>{{cite journal | vauthors = Schaadt R, Sweeney D, Shinabarger D, Zurenko G | title = In vitro activity of TR-700, the active ingredient of the antibacterial prodrug TR-701, a novel oxazolidinone antibacterial agent | journal = Antimicrobial Agents and Chemotherapy | volume = 53 | issue = 8 | pages = 3236–3239 | date = August 2009 | pmid = 19528279 | pmc = 2715649 | doi = 10.1128/AAC.00228-09 }}</ref> Once activated, tedizolid exerts its bacteriostatic microbial activity through inhibition of protein synthesis by binding to the ] ribosomal subunit (on the acceptor site) of the bacteria.<ref name="Sivextro FDA label"/>
]
{{clear-left}}

==Pharmacokinetic/pharmacodynamic (PK/PD) properties==
Tedizolid tablets have an oral bioavailability >90%. Tedizolid has higher binding to plasma proteins (80%), longer half-life, and a larger volume of distribution compared to linezolid. It is primarily metabolized by the liver as an inactive sulphate conjugate (phase II reaction), with no metabolism by cytochrome P-450 enzymes. Less than 20% of the drug is excreted unchanged in the urine. Tedizolid bactericidal activity on VRE and MRSA is time dependent. Correlations are closest between fAUC24/MIC and the tedizolid PK/PD index against MRSA and VRE. To achieve 1 log10 kill, tedizolid fAUC24/MIC in neutropenic mouse models with a thigh infection with VRE and MRSA should be 14.2 and 138.5, respectively. The post-antibiotic effects of tedizolid against VRE and MRSA are 2.39 and 0.99 h, respectively.<ref>{{cite journal | vauthors = Carcione D, Intra J, Andriani L, Campanile F, Gona F, Carletti S, Mancini N, Brigante G, Cattaneo D, Baldelli S, Chisari M, Piccirilli A, Di Bella S, Principe L | display-authors = 6 | title = New Antimicrobials for Gram-Positive Sustained Infections: A Comprehensive Guide for Clinicians | journal = Pharmaceuticals | volume = 16 | issue = 9 | pages = 1304 | date = September 2023 | pmid = 37765112 | pmc = 10536666 | doi = 10.3390/ph16091304 | doi-access = free }}</ref>

==Clinical trials==
Tedizolid proved its noninferiority to linezolid in two phase-III trials, known as the ESTABLISH trials.<ref>. Accessed March 16, 2015</ref>

Tedizolid is the second treatment approved by the FDA under the new federal law ] (known as the GAIN Act).<ref>{{cite news |url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm320643.htm |title=New FDA task force will support innovation in antibacterial drug development |date=September 2012 }}</ref><ref name ="GAIN">{{cite news |url=http://blogs.fda.gov/fdavoice/index.php/tag/gain-act/ |title=Three encouraging steps towards new antibiotics |date=September 2014 }}</ref> New antibiotics manufactured under this new act will be designed as a ] (QIDP), allowing an expedited review by the FDA and an additional five years of market exclusivity.<ref name="GAIN"/>

==Adverse effects==
The most common adverse effects found in the clinical trials were nausea, headache, diarrhea, vomiting, and dizziness.<ref name="Sivextro FDA label"/> Tedizolid has also been found to have hematologic (blood) effects, as shown in ] studies in which subjects exposed to doses longer than 6 days showed a possible dose and duration effect on hematologic parameters.<ref name="Sivextro FDA label"/> Its safety in patients with decreased levels of white blood cells has not been established.<ref name="FDA Approval"/> Patients on tedizolid are also at low risk of peripheral and ], similar to other members of the oxazolidinone class.<ref name="Sivextro FDA label"/>

== References ==
{{reflist}}

== External links ==
* {{cite web | title=Tedizolid Injection: MedlinePlus Drug Information | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a614039.html }}

{{Other antibacterials}}
{{Portal bar | Medicine}}

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