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
Trioxaquines: hybrid molecules for the treatment of malaria.	2010-12	21180649
Synthesis and antimalarial assessment of a new series of orally active amino-functionalized spiro 1,2,4-trioxanes.	2010-11-11	20936847
A suitable preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and their ring homologs with a reusable Preyssler heteropolyacid as catalyst.	2010-11	19572201
Interspecies comparison of the pharmacokinetics and oral bioavailability of 99-357, a potent synthetic trioxane antimalarial compound.	2010-10-09	20599503
Purified E255L mutant SERCA1a and purified PfATP6 are sensitive to SERCA-type inhibitors but insensitive to artemisinins.	2010-08-20	20530490
Chain branching and termination in the low-temperature combustion of n-alkanes: 2-pentyl radical + O2, isomerization and association of the second O2.	2010-07-29	20604539
The pharmaceutical death-ride of dihydroartemisinin.	2010-07-22	20649950
(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.	2010-06-26	21588040
Thiazole, oxadiazole, and carboxamide derivatives of artemisinin are highly selective and potent inhibitors of Toxoplasma gondii.	2010-05-13	20373807
Artemisinin-derived dimers have greatly improved anti-cytomegalovirus activity compared to artemisinin monomers.	2010-04-28	20442781
Formaldehyde in the indoor environment.	2010-04-14	20067232
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.	2009-12-10	19586052
Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid.	2009-08	19426722
Liquid chromatographic tandem mass spectrometric assay for quantification of 97/78 and its metabolite 97/63: a promising trioxane antimalarial in monkey plasma.	2009-07-15	19520624
Antimalarial peroxide dyads from natural artemisinin and hydroxyalkylated 1,2,4-trioxanes.	2009-05-28	19402629
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.	2009-02-26	19186946
Diastereoselective preparation of substituted delta-valerolactones. synthesis of (3R,4S)- and (3R,4R)-simplactones.	2009-02-06	19102676
Ferrocenium salts mediate para-tert-butylcalixarene synthesis.	2008-11-30	19009063
New strategy for the construction of epoxy-bridged tetrahydropyran frameworks from trioxane precursors: application to a concise synthesis of a Riesling acetal.	2008-11-07	18844411
Piperidine dispiro-1,2,4-trioxane analogues.	2008-11-01	18845438
Accretion reactions of octanal catalyzed by sulfuric acid: product identification, reaction pathways, and atmospheric implications.	2008-10-01	18939538
Elucidation of the natural artemisinin decomposition route upon iron interaction: a fine electronic redistribution promotes reactivity.	2008-09-01	18701956
1,2,5,10,11,14-hexaoxadispiro[5.2.5.2]hexadecanes: novel spirofused bis-trioxane peroxides.	2008-08-19	18794783
Redetermination of 2,4,6-tricyclo-hexyl-1,3,5-trioxane.	2008-06-19	21202930
Photoinduced oxygen capture on immobilized dienone systems. First solid-phase synthesis of trioxane scaffolds.	2008-04-26	18435562
Two-step synthesis of achiral dispiro-1,2,4,5-tetraoxanes with outstanding antimalarial activity, low toxicity, and high-stability profiles.	2008-04-10	18341274
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.	2008-03-15	18316253
Malaria-infected mice are cured by oral administration of new artemisinin derivatives.	2008-02-28	18232653
[Synthesis and antiviral activity of lupane triterpenoids with modified cycle E].	2008-01-05	18173126
Hybrid molecules with a dual mode of action: dream or reality?	2008-01	17665872
Evaluation of some adamantane-based synthetic trioxanes against Plasmodium knowlesi in rhesus monkeys.	2007-11-10	17976659
Conversion of antimalarial drug artemisinin to a new series of tricyclic 1,2,4-trioxanes1.	2007-10-11	17877363
Ensuring sustained ACT production and reliable artemisinin supply.	2007-09-15	17868471
Role of transferrin receptor and the ABC transporters ABCB6 and ABCB7 for resistance and differentiation of tumor cells towards artesunate.	2007-08-29	17726528
Malaria-infected mice are cured by a single dose of novel artemisinin derivatives.	2007-05-17	17439113
New adamantane-based spiro 1,2,4-trioxanes orally effective against rodent and simian malaria.	2007-02-08	17266204
Reactions of artemisinin and arteether with acid: implications for stability and mode of antimalarial action.	2006-10-05	17004720
Quantitative NMR spectroscopy of complex technical mixtures using a virtual reference: chemical equilibria and reaction kinetics of formaldehyde-water-1,3,5-trioxane.	2006-07	16773212
8-(1-Naphthalen-2-yl-vinyl)-6,7,10-trioxaspiro (4.5) decane, a new 1,2,4-trioxane effective against rodent and simian malaria.	2006-02	16275088
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.	2005-11	16222725
New orally active spiro 1,2,4-trioxanes with high antimalarial potency.	2005-10-15	16105737
Conformational pathways of saturated six-membered rings. A static and dynamical density functional study.	2005-09-15	16834195
A high throughput approach for simultaneous estimation of multiple synthetic trioxane derivatives using sample pooling for pharmacokinetic studies.	2005-02-07	15664752
Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities.	2005-02-01	15664819
Synthesis and antimalarial activity of 6-cycloalkylvinyl substituted 1,2,4-trioxanes.	2004-11-15	15498651
HPLC-UV method for assaying 99/357, a synthetic trioxane antimalarial derivative in rat and rabbit serum.	2004-10-29	15496331
Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore.	2004-09-02	15330581
Synthesis and antimalarial activity of trioxaquine derivatives.	2004-04-02	15054749
Protein binding and alpha : beta anomer ratio of dihydroartemisinin in vivo.	2004-04	15025754
Anticancer and antimalarial efficacy and safety of artemisinin-derived trioxane dimers in rodents.	2004-02-26	14971910

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:10:18 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:18 GMT 2025`
Record UNII	46BNU65YNY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

S-TRIOXANE

Preferred Name

English

1,3,5-TRIOXANE

Systematic Name

English

1,3,5-TRIOXANE [HSDB]

Common Name

English

TRIOXAN

Systematic 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