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Artemisinin

Artemisinin Struktur
63968-64-9
CAS-Nr.
63968-64-9
Englisch Name:
Artemisinin
Synonyma:
ARTEMETHER;ARTEANNUIN;ARTEMISIA ANNUA;QINGHAOSU;3,12-epoxy-12h-pyranol(4,3-j)-1,2-benzodioxepin-10(3h)-one,octahydro-3,6,9-tri;Astemisinin;huanghuahaosu;Artemisinine,98%;octahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin-10(;(3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epox12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
CBNumber:
CB3387975
Summenformel:
C15H22O5
Molgewicht:
282.33
MOL-Datei:
63968-64-9.mol

Artemisinin Eigenschaften

Schmelzpunkt:
156-157 °C (lit.)
alpha 
76 º (c=0.5,MeOH)
Siedepunkt:
344.94°C (rough estimate)
Dichte
1.0984 (rough estimate)
Brechungsindex
75 ° (C=0.5, MeOH)
storage temp. 
-20°C
L?slichkeit
Soluble to 100mM in DMSO and to 75mM in ethanol
Aggregatzustand
White to off-white crystalline solid.
Farbe
Needles
Optische Aktivit?t
[α]20/D +76°, c = 0.5 in methanol
Merck 
14,817
Stabilit?t:
Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides. May absorb, and react with, carbon dioxide from the air.
InChI
InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
InChIKey
BLUAFEHZUWYNDE-NNWCWBAJSA-N
SMILES
O1[C@]23[C@@]4([H])O[C@@](C)(CC[C@@]2([H])[C@H](C)CC[C@@]3([H])[C@@H](C)C(=O)O4)O1
LogP
2.900
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
S-S?tze: 22-24/25
WGK Germany  2
RTECS-Nr. KD4170000
HS Code  29322985
Toxizit?t LD50 in mice (mg/kg): 5105 orally; 2800 i.m.; 1558 i.p. (Koch); LD50 in mice, rats (mg/kg): 4228, 5576 orally; 3840, 2571 i.m. (China Cooperative Research Group on Qinghaosu)
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H242 Erw?rmung kann Brand verursachen. Organische Peroxide Typen C & D Achtung
Warnung
GHS hazard pictogramssrc="/GHS02.jpg" width="20" height="20" /> P210, P220, P234, P280, P370+P378,P403+P235, P411, P420, P501
H400 Sehr giftig für Wasserorganismen. Kurzfristig (akut) gew?ssergef?hrdend Kategorie 1 Warnung GHS hazard pictogramssrc="/GHS09.jpg" width="20" height="20" /> P273, P391, P501
H410 Sehr giftig für Wasserorganismen mit langfristiger Wirkung. Langfristig (chronisch) gew?ssergef?hrdend Kategorie 1 Warnung GHS hazard pictogramssrc="/GHS09.jpg" width="20" height="20" /> P273, P391, P501
Sicherheit
P210 Von Hitze, hei?en Oberfl?chen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P220 Von Kleidung und anderen brennbaren Materialien fernhalten.
P234 Nur im Originalbeh?lter aufbewahren.
P273 Freisetzung in die Umwelt vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P391 Verschüttete Mengen aufnehmen.
P410 Vor Sonnenbestrahlung schützen.
P420 Von anderen Materialien entfernt aufbewahren.

Artemisinin Chemische Eigenschaften,Einsatz,Produktion Methoden

S-S?tze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.

Beschreibung

Artemisinin, a sesquiterpene isolated from a traditional Chinese remedy (quinghao), is useful in the treatment of Fafciparum malaria, including infections caused by chloroquine resistant strains. It is reported to clear parasitemia quicker than i.v. quinine, and is effective in cerebral malaria.

Chemische Eigenschaften

Crystalline Solid

Physikalische Eigenschaften

Appearance: colorless needles or white crystalline powder. Solubility: practically insoluble in water, very soluble in dichloromethane, freely soluble in acetone and ethyl acetate, and soluble in glacial acetic acid, methanol, and ethanol. Melting point: 150–153?°C. Specific optical rotation: +75 to +78°.

History

The discovery of artemisinin dramatically changes the landscape to combat malaria and leads to a paradigm shift in antimalarial drug development.
However, the discovery of artemisinin is the first stage; the development of artemisinin derivatives and their compound preparations is another important stage. Based on artemisinin, scientists obtained artemisinin ether derivatives by semisynthetic method. After screening of antimalarial activity, artemether was found. To further improve the solubility of artemisinin derivatives, artesunate was also found. The discovery of artesunate makes artemisinin and its derivatives much easier to promote, and more convenient dosage forms to treat malaria enriched the clinic application of artemisinin and its derivatives .

Verwenden

Artemisinin inhibits angiogenesis by down-regulating HIF-1α and VEGF expression in mouse embryonic stem cells. Artemisinin crosses the blood-brain barrier and is an inhibitor of human NOS2 (iNOS).

Indications

Clinically, artemisinin is mainly used to treat malaria symptoms, malignant cerebral malaria, uncomplicated malaria, and severe malaria. Combined with different antimalarial can delay and prevent resistance of malaria parasites. In additional, artemisinin can also be used for systemic lupus erythematosus or discoid lupus erythematosus. Currently, artemisinin derivatives and their compound preparations are widely used in clinic.

Definition

ChEBI: A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.

Antimicrobial activity

Artemisinins are active against the erythrocytic and gametocyte stages of chloroquine-sensitive and chloroquine-resistant strains of P. falciparum and other malaria parasites. Two anomers of artemether are produced on synthesis, α-artemether and β-artemether, of which the latter has higher antimalarial activity. Activity against the protozoa Tox. gondii and Leishmania major and the helminth Schistosoma mansoni has been demonstrated in experimental models.

Acquired resistance

Resistance caused, for example, by changes in the plasmodial endoplasmic reticulum ATPase has been shown in experimental models. There have been clinical reports of reduced susceptibility to treatment with artesunate in Cambodia.

Allgemeine Beschreibung

The artemisinin series are the newest of the antimalarialdrugs and are structurally unique when comparedwith the compounds previously and currently used. Theparent compound, artemisinin, is a natural product extractedfrom the dry leaves of Artemisia Annua (sweetwormwood). The plant has to be grown each year fromseed because mature plants may lack the active drug. The growing conditions are critical to maximize artemisininyield. Thus far, the best yields have been obtained fromplants grown in North Vietnam, Chongqing province inChina, and Tanzania.

Pharmazeutische Anwendungen

Artemisinin (qinghaosu), a compound derived from a plant used in traditional Chinese medicine, Artemisia annua, has been used extensively in East Asia and Africa for the treatment of malaria. This drug, and derivatives that have higher intrinsic antimalarial activity (artesunate, artemether and arteether), have replaced quinine as a treatment of falciparum malaria in many countries, normally in combination with other antimalarials. A semisynthetic derivative, artemisone, which has higher efficacy than artesunate and lower toxicity potential, is in development. Artemisinin and its derivatives also show broad antiprotozoal, anthelmintic and antiviral activities.
The novel structure, containing an endoperoxide bridge, has stimulated the development of semisynthetic and synthetic dioxane, trioxane and tetroxane compounds with activity against Plasmodium spp. and Schistosoma spp. Some of these synthetic trioxalanes are now in clinical development with Medicines for Malaria Venture and other organizations.

Biologische Aktivit?t

Antimalarial agent; interacts with heme to produce carbon-centred free radicals, causes protein alkylation and damages parasite microorganelles and membranes. Also selectively inhibits the P-type ATPase (PfATP6) of Plasmodium falciparum (K i ~ 150 nM). Displays antiangiogenic effects in mouse embryonic stem cell-derived embryoid bodies.

Pharmakokinetik

Oral absorption: Incomplete
Cmax 500 mg oral: 0.4 mg/L after 1.8 h
Plasma half-life (dihydroartemisinin): 40–60 min
Volume of distribution: c. 0.25 L/kg
Plasma protein binding (artemether): 77%
Artemisinins are concentrated by erythrocytes and are rapidly hydrolyzed to dihydroartemisinin. They are hydroxylated by cytochromes 2B6, 2C19 and 3A4; the derivatives induce this metabolism. After injection, peak plasma concentrations are reached within 1–3 h, when levels of dihydroartemisinin are included. The elimination half-life of intravenous artesunate is <30 min; artemether appears to have a much longer half-life (4–11 h).

Pharmakologie

The mechanism of artemisinins is not known, but the most widely accepted theory is that they are first activated through cleavage after reacting with haem and iron(II) oxide, which results in the generation of free radicals that in turn damage susceptible proteins, resulting in the death of the parasite .
Artemisinin and its derivatives also show a good antitumor effect , which is mainly via (1) apoptosis, ferroptosis, or necrosis; (2) anti-angiogenesis; (3) oxidative stress; (4) tumor suppressor genes; and (5) protein targeting. In addition, artemisinin can exhibit antiarrhythmic, anti-fibrotic, and immunomodulating effects.

Clinical Use

Malaria (including cerebral malaria), in combination with other antimalarials.

Nebenwirkungen

A few toxic effects in addition to drug-induced fever and a reversible decrease in reticulocyte counts have been reported. High-dose studies in animal models show neurotoxicity and reproducible dose-related neuropathic lesions; dihydroartemisinin is a toxic metabolite but the precise causes of neurotoxicity are not clear. Embryotoxicity of artemisinin and derivatives has been reported in rodent and primate models, probably due to depletion of erythroblasts.

Sicherheitsprofil

Moderately toxic by ingestion,intramuscular, and intraperitoneal routes. When heated todecomposition it emits acrid smoke and fumes.

Artemisinin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Artemisinin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 719)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Shaanxi Haibo Biotechnology Co., Ltd
+undefined18602966907
qinhe02@xaltbio.com China 997 58
Wuhan Fortuna Chemical Co.,Ltd
+8618007136271
hk@fortunachem.com China 5998 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12834 58
Hebei Chuanghai Biotechnology Co,.LTD
+86-13131129325
sales1@chuanghaibio.com China 5889 58
Hebei Weibang Biotechnology Co., Ltd
+8617732866630
bess@weibangbio.com China 18151 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971
deasea125996@gmail.com China 2472 58
Wuhan Haorong Biotechnology Co.,ltd
+86-18565342920; +8618565342920
sales@chembj.net China 289 58
Anhui Ruihan Technology Co., Ltd
+8617756083858
daisy@anhuiruihan.com China 973 58
airuikechemical co., ltd.
+86-18353166132 +86-18353166132
sales02@airuikechemical.com China 983 58
Hangzhou Hyper Chemicals Limited
+86-0086-57187702781 +8613675893055
info@hyper-chem.com China 295 58

63968-64-9()Verwandte Suche:


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