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Revision as of 17:30, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473502657 of page 2-Oxazolidone for the Chem/Drugbox validation project (updated: '').		Latest revision as of 18:18, 3 December 2024 edit Cyfal (talk | contribs)Extended confirmed users, Pending changes reviewers64,270 editsm spelling (WP:Typo Team)
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 445108800		| verifiedrevid = 477215129
⚫	| Name = 2-Oxazolidone
	| ImageFileL1 = 2-Oxazolidone.png		| Name = 2-Oxazolidone
		⚫	| ImageFileL1 = 2-Oxazolidone structure.svg
	| ImageFileR1 = Oxazolidin-2-one-3D-balls.png		| ImageFileR1 = Oxazolidin-2-one-3D-balls.png
	<!-- | ImageSize = 100px -->
	| ImageName =		| ImageName =
	| IUPACName = 1,3-Oxazolidin-2-one		| PIN = 1,3-Oxazolidin-2-one
			| OtherNames = 1,3-Oxazolidin-2-one, 2-Oxo-1,3-oxazolidine, 2-Oxotetrahydro-1,3-oxazole
	| OtherNames = 2-Oxazolidone<br />2-Oxazolidinone
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| SMILES = O=C1OCCN1		| SMILES = O=C1OCCN1
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C06695		| KEGG = C06695
	| InChI = 1/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5)		| InChI = 1/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5)
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	| StdInChIKey = IZXIZTKNFFYFOF-UHFFFAOYSA-N		| StdInChIKey = IZXIZTKNFFYFOF-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 497-25-6		| CASNo = 497-25-6
			| UNII_Ref = {{fdacite|correct|FDA}}
	| CASNo_valid = yes
			| UNII = Z4D49W92PP
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 66579		| ChemSpiderID = 66579
	| RTECS =		| RTECS =
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>3</sub>H<sub>5</sub>NO<sub>2</sub>		| Formula = C<sub>3</sub>H<sub>5</sub>NO<sub>2</sub>
	| MolarMass = 87.077 g/mol		| MolarMass = 87.077 g/mol
	| Appearance = Solid		| Appearance = white or colorless solid
	| Density =		| Density =
	| Solubility =		| Solubility =
			| MeltingPtC = 86 to 89
	| MeltingPt = 86–89 °C
	| BoilingPt = 220 °C at 48 ]		| BoilingPtC = 220
			| BoilingPt_notes = at 48 ]
⚫	| pKa =
	| pKb =		| pKa =
			| pKb =
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct =		| CrystalStruct =
	| Dipole =		| Dipole =
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| RPhrases =
	| SPhrases =
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherCpds = ]		| OtherCompounds = ]
	}}		}}
	}}		}}
			'''2-Oxazolidinone''' is a ] ] containing both nitrogen and oxygen in a 5-membered ring.
			== Synthesis and occurence==
			The compound arises by the reaction of an ethanolamine and dimethylcarbonate<ref>{{cite journal |doi=10.15227/orgsyn.062.0149 |title=Synthesis and Diels–Alder Rearctions of 3-Acetyl-2(3H)-Oxazolone: 6-Amino-3,4-dimethyl-cis-3-cyclohexen-1-ol |journal=Organic Syntheses |date=1984 |volume=62 |page=149|author=
			Karl-Heinz Scholz, Hans-Georg Heine, Willy Hartmann }}</ref> or related ] equivalents.<ref>{{cite journal |doi=10.15227/orgsyn.075.0045 |title=(4R,5S)-4,5-Diphenyl-3-Vinyl-2-Oxazolidinone |journal=Organic Syntheses |date=1998 |volume=75 |page=45|author=T. Akiba, O. Tamura, S. Terashima }}</ref>
			It is one of waste products generated in ] due to cyclization of ] carbamate.<ref>{{Cite journal |last=Salim |first=S. R. S. |date=2021-03-01 |title=Treatment of amine wastes generated in industrial processes |url=https://iopscience.iop.org/article/10.1088/1757-899X/1092/1/012051 |journal=IOP Conference Series: Materials Science and Engineering |volume=1092 |issue=1 |pages=012051 |doi=10.1088/1757-899x/1092/1/012051 |issn=1757-8981|doi-access=free }}</ref>
			===History===
			The compound was first reported in 1888 by German chemist ]. While investigating reactions of bromoethylamine hydrobromide, he treated it with ] and isolated a product with melting point around 90–91°C. He determined its empirical formula correctly, but neither gave it a specific name not studied its properties.<ref>{{Cite journal |last=Gabriel |first=S. |date=1888 |title=Ueber einige Derivate des Aethylamins |url=https://books.google.com/books?id=d_1hofkLJ-wC&pg=PA568 |journal=Berichte der Deutschen Chemischen Gesellschaft |language=de |volume=21 |issue=1 |pages=566–575 |doi=10.1002/cber.188802101103 |issn=0365-9496}}</ref>
			Nine years later Gabriel returned to the topic together with G. Eschenbach, developing a more efficient synthesis using ] instead of the silver salt. They referred to the compound as "Oxäthylcarbaminsäureanhydrid" (hydroxyethylcarbamic acid anhydride), recognizing its relationship to ethanolamine and its cyclic structure. Their 1897 paper focused on optimizing the yield of oxazolidone and investigating some of its reactions, such as its conversion to 1-(2-hydroxyethyl)-3-phenylurea upon treatment with aniline.<ref>{{Cite journal |last1=Gabriel |first1=S. |last2=Eschenbach |first2=G. |date=September 1897 |title=Notizen über Bromäthylamin und Vinylamin |url=https://books.google.com/books?id=jAvVlrHhI1kC&pg=PA2494 |journal=Berichte der Deutschen Chemischen Gesellschaft |language=de |volume=30 |issue=3 |pages=2494–2497 |doi=10.1002/cber.18970300324 |issn=0365-9496}}</ref>
			==Substituted oxazolidinones==
			===Evans auxiliaries===
			Oxazolidinones are useful as ], which are of interest for ]. In a common implementation, an ] substrate reacts with a chiral oxazolidinone to form an ]. Substituents at the 4 and 5 position of the oxazolidinone direct any ] to the alpha position of the carbonyl of the substrate.<ref>{{cite journal |doi=10.15227/orgsyn.068.0083 |title=Diastereoselective Aldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2S,3S)-3-Hydroxy-3-Phenyl-2-Methylpropanoic Acid |journal=Organic Syntheses |date=1990 |volume=68 |page=83|author=James R. Gage, David A. Evans }}</ref> Asymmetric Diels-Alder reactions are also enabled by these auxiliaries.<ref>{{cite journal |doi=10.15227/orgsyn.071.0030 |title=Enantioselective, Catlytic Diels-Alder Reaction: (1S-endo)-3-(Bicyclo&#91;2.2.1&#93;Hept-5-en-2-ylcarbonyl)-2-Oxazolidinone |journal=Organic Syntheses |date=1993 |volume=71 |page=30|author=S. Pikul, E. J. Corey }}</ref>
			===Pharmaceuticals===
			Oxazolidinones are found in some antimicrobials. Oxazolidinones ] by interfering with the binding of N-formylmethionyl-tRNA to the ribosome.<ref>{{Cite journal
			| last1 = Shinabarger | first1 = D.
			| doi = 10.1517/13543784.8.8.1195
			| title = Mechanism of action of the oxazolidinone antibacterial agents
			| journal = Expert Opinion on Investigational Drugs
			| volume = 8
		⚫	| issue = 8
			| pages = 1195–1202
			| year = 1999
			| pmid = 15992144
			}}</ref> (See ])
			Some of the most important oxazolidinones are antibiotics.<ref>{{cite book|title=Antibiotics: Targets, Mechanisms and Resistance|chapter=A Chemist’s Survey of Different Antibiotic Classes
			|author=Sonia Ilaria Maffioli|editor1 = Claudio O. Gualerzi |editor2=Letizia Brandi |editor3=Attilio Fabbretti |editor4=Cynthia L. Pon|year=2014|publisher=Wiley-VCH|isbn=9783527659685}}</ref>
			Examples of oxazolidinone-containing antibiotics:
			* ] (Zyvox), which is available for ] administration and also has the advantage of having excellent oral ].
			* ], which appears to have excellent, targeted bactericidal activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics.<ref>{{cite journal |author1=Wookey, A. |author2=Turner, P. J. |author3=Greenhalgh, J. M. |author4=Eastwood, M. |author5=Clarke, J. |author6=Sefton, C. | title = AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro | journal = Clinical Microbiology and Infection | year = 2004 | volume = 10 | issue = 3 | pages = 247–254 | pmid=15008947 | doi = 10.1111/j.1198-743X.2004.00770.x| doi-access=free }}</ref>
			]
			* ], (Sivextro) which is approved for acute skin infections
			* ] (RX-1741) has completed some phase-II clinical trials.<ref>{{cite web|url=http://www.rib-x.com/pipeline/rx_1741 |title=Rx 1741 |publisher=Rib-X Pharmaceuticals |year=2009 |access-date=2009-05-17 |url-status=dead |archive-url=https://web.archive.org/web/20090226201337/http://www.rib-x.com/pipeline/rx_1741 |archive-date=2009-02-26 }}</ref>
			* ] (MRX-I) has reported phase 1 data<ref>{{cite journal|doi=10.1021/jm401931e | volume=57 | issue=11 | title=New Potent Antibacterial Oxazolidinone (MRX-I) with an Improved Class Safety Profile | year=2014 | journal=Journal of Medicinal Chemistry | pages=4487–4497 | last1 = Gordeev | first1 = Mikhail F. | last2 = Yuan | first2 = Zhengyu Y.| pmid=24694071 }}</ref> and phase III data.<ref>{{cite journal | doi = 10.1093/jac/dkac073 | title = A Phase III multicentre, randomized, double-blind trial to evaluate the efficacy and safety of oral contezolid versus linezolid in adults with complicated skin and soft tissue infections | year = 2022 | last1 = Zhao | first1 = Xu | last2 = Huang | first2 = Haihui | last3 = Yuan | first3 = Hong | last4 = Yuan | first4 = Zhengyu | last5 = Zhang | first5 = Yingyuan | journal = Journal of Antimicrobial Chemotherapy | volume = 77 | issue = 6 | pages = 1762–1769 | pmid = 35265985 }}</ref> In 2021, a new drug summary was published by ADIS Press.<ref>{{Cite journal | doi = 10.1007/s40265-021-01576-0 | title = Contezolid: First Approval | year = 2021 | last1 = Hoy | first1 = Sheridan M. | journal = Drugs | volume = 81 | issue = 13 | pages = 1587–1591 | pmid = 34365606 | pmc = 8536612 }}</ref> In June 2021, marketing approval was granted by the Chinese National Medical Products Administration (NMPA) for use of oral contezolid in moderate to severe complicated skin and skin structure infections.<ref>{{cite web | url = http://www.micurx.com/703.html | title = China NMPA Approves MicuRx's Contezolid for Treatment of Drug-Resistant Bacterial Infection – MicuRx Pharmaceuticals, Inc }}</ref> In June 2022, contezolid oral tablets and contezolid acefosamil IV (a prodrug of contezolid) began Phase 3 global clinical trials in moderate to severe diabetic foot infections.<ref>ClinicalTrials.gov Identifier: NCT05369052 </ref> An additional global Phase 3 study is planned for acute bacterial skin and skin structure infections (ABSSSI) for the combination of contezolid and contezolid acefosamil.
			* An oxazolidinone derivative used for other purposes is ], which is approved by the U.S. FDA for venous thromboembolism prophylaxis.
			]
			A first commercially available 1,3-oxazolidinone is the antibiotic ].
			==See also==
			* ] – the ring without the carbonyl group
			* ] – the unsaturated analogues
			==References==
			<references />
			==External links==
			*
			{{Protein synthesis inhibitor antibiotics}}
			{{DEFAULTSORT:Oxazolidone, 2-}}
			]
			]