1,3,5-TRIOXANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H6O3
Molecular Weight	90.0779
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1OCOCO1

InChI

InChIKey=BGJSXRVXTHVRSN-UHFFFAOYSA-N

InChI=1S/C3H6O3/c1-4-2-6-3-5-1/h1-3H2

HIDE SMILES / InChI

Molecular Formula	C3H6O3
Molecular Weight	90.0779
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Quantitative (13)C NMR analysis of lignins with internal standards.	2001 Aug	11513630
Antimalarial simplified 3-aryltrioxanes: synthesis and preclinical efficacy/toxicity testing in rodents.	2001 Sep 13	11543673
Malaria: new chemotherapeutic peroxide drugs.	2002 Dec	12370042
Antimalarial chemotherapeutic peroxides: artemisinin, yingzhaosu A and related compounds.	2002 Dec 4	12435451
Alkylation of manganese(II) tetraphenylporphyrin by a synthetic antimalarial trioxane.	2003 Aug 21	12968336
Chloroquine and artemisinin: six decades of research--what next?	2003 Jul	12861472
Protein binding and alpha : beta anomer ratio of dihydroartemisinin in vivo.	2004 Apr	15025754
Development of artemisinin and its structurally simplified trioxane derivatives as antimalarial drugs.	2004 Feb	14744559
Anticancer and antimalarial efficacy and safety of artemisinin-derived trioxane dimers in rodents.	2004 Feb 26	14971910
Antimalarial and antitumor evaluation of novel C-10 non-acetal dimers of 10beta-(2-hydroxyethyl)deoxoartemisinin.	2004 Feb 26	14971909
Synthesis and antimalarial activity of 6-cycloalkylvinyl substituted 1,2,4-trioxanes.	2004 Nov 15	15498651
Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities.	2005 Feb 1	15664819
Enantiomeric 1,2,4-trioxanes display equivalent in vitro antimalarial activity versus Plasmodium falciparum malaria parasites: implications for the molecular mechanism of action of the artemisinins.	2005 Nov	16222725
New orally active spiro 1,2,4-trioxanes with high antimalarial potency.	2005 Oct 15	16105737
Quantitative NMR spectroscopy of complex technical mixtures using a virtual reference: chemical equilibria and reaction kinetics of formaldehyde-water-1,3,5-trioxane.	2006 Jul	16773212
Role of transferrin receptor and the ABC transporters ABCB6 and ABCB7 for resistance and differentiation of tumor cells towards artesunate.	2007 Aug 29	17726528
Evaluation of some adamantane-based synthetic trioxanes against Plasmodium knowlesi in rhesus monkeys.	2007 Nov 10	17976659
[Synthesis and antiviral activity of lupane triterpenoids with modified cycle E].	2007 Nov-Dec	18173126
Conversion of antimalarial drug artemisinin to a new series of tricyclic 1,2,4-trioxanes1.	2007 Oct 11	17877363
Ensuring sustained ACT production and reliable artemisinin supply.	2007 Sep 15	17868471
Hybrid molecules with a dual mode of action: dream or reality?	2008 Jan	17665872
Redetermination of 2,4,6-tricyclo-hexyl-1,3,5-trioxane.	2008 Jun 19	21202930
A sensitive and selective liquid chromatographic tandem mass spectrometric assay for simultaneous quantification of novel trioxane antimalarials in different biomatrices using sample-pooling approach for high throughput pharmacokinetic studies.	2008 Mar 15	18316253
Piperidine dispiro-1,2,4-trioxane analogues.	2008 Nov 1	18845438
Ferrocenium salts mediate para-tert-butylcalixarene synthesis.	2008 Nov 30	19009063
Accretion reactions of octanal catalyzed by sulfuric acid: product identification, reaction pathways, and atmospheric implications.	2008 Oct 1	18939538
Elucidation of the natural artemisinin decomposition route upon iron interaction: a fine electronic redistribution promotes reactivity.	2008 Sep 1	18701956
Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid.	2009 Aug	19426722
Malaria-infected mice live until at least day 30 after a new monomeric trioxane combined with mefloquine are administered together in a single low oral dose.	2009 Dec 10	19586052
Malaria-infected mice are cured by a single oral dose of new dimeric trioxane sulfones which are also selectively and powerfully cytotoxic to cancer cells.	2009 Feb 26	19186946
Diastereoselective preparation of substituted delta-valerolactones. synthesis of (3R,4S)- and (3R,4R)-simplactones.	2009 Feb 6	19102676
Liquid chromatographic tandem mass spectrometric assay for quantification of 97/78 and its metabolite 97/63: a promising trioxane antimalarial in monkey plasma.	2009 Jul 15	19520624
Antimalarial peroxide dyads from natural artemisinin and hydroxyalkylated 1,2,4-trioxanes.	2009 May 28	19402629
Formaldehyde in the indoor environment.	2010 Apr 14	20067232
Artemisinin-derived dimers have greatly improved anti-cytomegalovirus activity compared to artemisinin monomers.	2010 Apr 28	20442781
Purified E255L mutant SERCA1a and purified PfATP6 are sensitive to SERCA-type inhibitors but insensitive to artemisinins.	2010 Aug 20	20530490
Trioxaquines: hybrid molecules for the treatment of malaria.	2010 Dec	21180649
The pharmaceutical death-ride of dihydroartemisinin.	2010 Jul 22	20649950
Chain branching and termination in the low-temperature combustion of n-alkanes: 2-pentyl radical + O2, isomerization and association of the second O2.	2010 Jul 29	20604539
(1R,3S,4R,4aS,7R,7aS,10R,12aR)-3-Azido-4,7,10-trimethyl-1,10-epidioxy-per-hydropyrano[4,3-j][1,2]benzodiox-epine.	2010 Jun 26	21588040
Thiazole, oxadiazole, and carboxamide derivatives of artemisinin are highly selective and potent inhibitors of Toxoplasma gondii.	2010 May 13	20373807
A suitable preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and their ring homologs with a reusable Preyssler heteropolyacid as catalyst.	2010 Nov	19572201
Synthesis and antimalarial assessment of a new series of orally active amino-functionalized spiro 1,2,4-trioxanes.	2010 Nov 11	20936847
Interspecies comparison of the pharmacokinetics and oral bioavailability of 99-357, a potent synthetic trioxane antimalarial compound.	2010 Oct 9	20599503

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:18:43 GMT 2023` Edited by `admin` on `Fri Dec 15 18:18:43 GMT 2023`
Record UNII	46BNU65YNY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,3,5-TRIOXANE

Systematic Name

English

1,3,5-TRIOXANE [HSDB]

Common Name

English

TRIOXAN

Systematic Name

English

S-TRIOXANE

Common Name

English

TRIOXYMETHYLENE

Common Name

English

SYM-TRIOXANE

Common Name

English

TRIOXANE

Systematic Name

English

TRIFORMOL

Common Name

English

NSC-26347

Code

English

S-TRIOXANE [MI]

Common Name

English

FORMALDEHYDE, TRIMER

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

203-812-5