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dihydroartemisinin

pharmaceuticals / chemical synthisis
2D:
3D:
CAS Number: 81496-82-4
FDA UNII: 6A9O50735X
Category: pharmaceuticals / chemical synthisis
IUPAC Name: dihydroartemisinin
InChI : InChI=1/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
Std.InChI: InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
InChIKey : BJDCWCLMFKKGEE-ISOSDAIHBH
Std.InChIKey: BJDCWCLMFKKGEE-ISOSDAIHSA-N
SMILES : O1[C@H](O)[C@@H]([C@@H]4CC[C@@H](C)[C@H]3[C@@]42OO[C@](O[C@@H]12)(C)CC3)C
MDL: MFCD00274495
Molar Refractivity : 71.71 ± 0.4 cm3 (est)
Parachor : 591.5 ± 6.0 cm3 (est)
Index of Refraction : 1.542 ± 0.03 (est)
Surface Tension : 45.6 ± 5.0 dyne/cm (est)
Density : 1.24 ± 0.1 g/cm3 (est)
Polarizability : 28.42 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search

Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 375.62 °C. @ 760.00 mm Hg (est)
Flash Point: 358.00 °F. TCC ( 181.00 °C. ) (est)
logP (o/w): 2.190 (est)
Soluble in:
water, 659.9 mg/L @ 25 °C (est)

Cosmetic Information:

None found

Suppliers:

BOC Sciences
For experimental / research use only.
Dihydroartemisinin 98%
Sigma-Aldrich
For experimental / research use only.
Dihydroartemisinin analytical standard, mixture of a and β isomers
Sinoway Industrial
For experimental / research use only.
Dihydroartemisinin

Safety Information:

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
pharmaceuticals / chemical synthisis
Recommendation for dihydroartemisinin usage levels up to:
not for fragrance use.
Recommendation for dihydroartemisinin flavor usage levels up to:
not for flavor use.

Safety References:

EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :456410
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0071939509

References:

NIST Chemistry WebBook:Search Inchi
Pubchem (cid):456410
Pubchem (sid):135066548

Other Information:

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):D07362
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

aertemiisia annua
Search Trop Picture

Synonyms:

dihxdroarteannui
dihydroartemisinine
dihyroartemisinin
3,12-epoxy-12-pyrano[4,3-j]-1,2-benzodioxepin-10-ol, decahydro-3,6,9-trimethyl-, (5aS,6R,8aS,9R,10S,12R,12aR)-
3,12-epoxy-12H-yrano(4,3-j)-1,2-benzodioxepin-10-ol, decahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)-
3,12-epoxy-12H-yrano[4,3-j]-1,2-benzodioxepin-10-ol, decahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)-
1,5,9-trimethyl-(1R,4S,5R,8S,9R,10S,12R,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol
(5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol

Articles:

PubMed:Daily home fortification with iron as ferrous fumarate versus NaFeEDTA: a randomised, placebo-controlled, non-inferiority trial in Kenyan children.
PubMed:Preclinical Efficacy and Safety Assessment of Artemisinin-Chemotherapeutic Agent Conjugates for Ovarian Cancer.
PubMed:Efficacy and Safety of High-Dose Ivermectin for Reducing Malaria Transmission (IVERMAL): Protocol for a Double-Blind, Randomized, Placebo-Controlled, Dose-Finding Trial in Western Kenya.
PubMed:The Importance of Blood Is Infinite: Conceptions of Blood as Life Force, Rumours and Fear of Trial Participation in a Fulani Village in Rural Gambia.
PubMed:Therapeutic effects of dihydroartemisinin and transferrin against glioblastoma.
PubMed:Effect of food on the pharmacokinetics of piperaquine and dihydroartemisinin.
PubMed:Amino acid efflux by asexual blood-stage Plasmodium falciparum and its utility in interrogating the kinetics of hemoglobin endocytosis and catabolism in vivo.
PubMed:Tailoring a Pediatric Formulation of Artemether-Lumefantrine for Treatment of Plasmodium falciparum Malaria.
PubMed:Population pharmacokinetics, tolerability, and safety of dihydroartemisinin-piperaquine and sulfadoxine-pyrimethamine-piperaquine in pregnant and nonpregnant Papua New Guinean women.
PubMed:Pharmacokinetics of a novel sublingual spray formulation of the antimalarial drug artemether in African children with malaria.
PubMed:Health & Demographic Surveillance System Profile: The Rufiji Health and Demographic Surveillance System (Rufiji HDSS).
PubMed:Optimizing the programmatic deployment of the anti-malarials artemether-lumefantrine and dihydroartemisinin-piperaquine using pharmacological modelling.
PubMed:Embryotoxicity and toxicokinetics of the antimalarial artesunate in rats.
PubMed:Advances in nanomedicines for malaria treatment.
PubMed:A screening-based approach to circumvent tumor microenvironment-driven intrinsic resistance to BCR-ABL+ inhibitors in Ph+ acute lymphoblastic leukemia.
PubMed:Dihydroartemisinin promotes angiogenesis during the early embryonic development of zebrafish.
PubMed:Inhibitory effect of dihydroartemisinin against phorbol ester-induced cyclooxygenase-2 expression in macrophages.
PubMed:Management of imported malaria in Europe.
PubMed:Cleavage mechanism and anti-tumor activity of 3,6-epidioxy-1,10-bisaboladiene isolated from edible wild plants.
PubMed:Monitoring of artemisinin, dihydroartemisinin, and artemether in environmental matrices using high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS).
PubMed:Malaria: severe, life-threatening.
PubMed:Early clinical development of artemether-lumefantrine dispersible tablet: palatability of three flavours and bioavailability in healthy subjects.
PubMed:Population pharmacokinetics of artesunate and dihydroartemisinin following single- and multiple-dosing of oral artesunate in healthy subjects.
PubMed:Understanding the pharmacokinetics of Coartem.
PubMed:Progress in the development of piperaquine combinations for the treatment of malaria.
PubMed:Bioavailability of a co-formulated combination of amodiaquine and artesunate under fed and fasted conditions. A randomised, open-label crossover study.
PubMed:The influence of food on the pharmacokinetics of piperaquine in healthy Vietnamese volunteers.
PubMed:Artemether-lumefantrine versus dihydroartemisinin-piperaquine for treating uncomplicated malaria: a randomized trial to guide policy in Uganda.
PubMed:Artemisinin-based combination therapies for uncomplicated malaria.
PubMed:Pharmacokinetics and electrocardiographic pharmacodynamics of artemether-lumefantrine (Riamet) with concomitant administration of ketoconazole in healthy subjects.
PubMed:Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues.
PubMed:Effects of dihydroartemisinin on fine structure of erythrocytic stages of Plasmodium berghei ANKA strain.
PubMed:Arteether toxicokinetics and pharmacokinetics in rats after 25 mg/kg/day single and multiple doses.
PubMed:The effect of grapefruit juice on the time-dependent decline of artemether plasma levels in healthy subjects.
PubMed:Clinical pharmacokinetics and pharmacodynamics and pharmacodynamics of artemether-lumefantrine.
PubMed:Morphologic effects of artemisinin in Plasmodium falciparum.
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