Antiparasitic drug Dosage and administration Clinical application Uses
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Artesunate

Antiparasitic drug Dosage and administration Clinical application Uses
Product Name
Artesunate
CAS No.
88495-63-0
Chemical Name
Artesunate
Synonyms
WR-256283;ARTENSUNATE;Artesunic Acid;Artemisinin monosuccinate;(3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol hydrogen succinate;4-Oxo-4-(((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid;Butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester;AsuMax;Cosunate;Saphnate
CBNumber
CB3157307
Molecular Formula
C19H28O8
Formula Weight
384.42
MOL File
88495-63-0.mol
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Artesunate Property

Melting point:
132-1350C
Boiling point:
431.1°C (rough estimate)
Density 
1.2076 (rough estimate)
refractive index 
1.4430 (estimate)
storage temp. 
2-8°C
solubility 
acetone: soluble33.4mg/mL
form 
crystalline powder
pka
4.28±0.17(Predicted)
color 
white to off-white
Merck 
14,818
BCS Class
3/1
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey
FIHJKUPKCHIPAT-AHIGJZGOSA-N
SMILES
C(O[C@@H]1O[C@]2([H])O[C@@]3(C)CC[C@@]4([H])[C@H](C)CC[C@@]([H])([C@H]1C)[C@]42OO3)(=O)CCC(O)=O
LogP
3.291 (est)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
24/25
WGK Germany 
3
HS Code 
29419090
Hazardous Substances Data
88495-63-0(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2573
Product name
Artesunate
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
300MG
Price
$186
Updated
2024/03/01
Sigma-Aldrich
Product number
A3731
Product name
Artesunate
Purity
from Artemisia annua
Packaging
100mg
Price
$342
Updated
2024/03/01
Sigma-Aldrich
Product number
1042850
Product name
Artesunate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
A2191
Product name
Artesunate
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$70
Updated
2024/03/01
TCI Chemical
Product number
A2191
Product name
Artesunate
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$201
Updated
2024/03/01
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Artesunate Chemical Properties,Usage,Production

Antiparasitic drug

Artesunate is a kind of commonly used anti-parasitic drug and belongs to reduced artemisinin succinate monoester, and is the derivative of artemisinin containing a sesquiterpene lactone structure, and has a stronger efficacy on treating parasite than artemisinin and is also effective on treating chloroquine resistant strains. It acts on the Plasmodium schizonts on the erythrocytic stage. It takes effect by inhibiting cytochrome oxidase through reduced artemisinin to achievement of the inhibition on the function of cytochrome oxidase of malaria parasite surface membrane-food vacuole membrane, mitochondrial membrane, and thus blocking the supplying of nutrition from the host cell cytoplasm. It has a strong killing effect on the asexual form of plasmodium with a rapid efficacy enabling the rapid control of the onset of malaria. It has good efficacy on treating cerebral malaria, falciparum malaria and vivax malaria with similar efficacy in treating chloroquine-resistant strain of the falciparum malaria, especially with more significant effect on treating cerebral malaria. It can quickly control the emergence of malaria but has no effect on falciparum malaria gametophyte. It has a shorter T1/2 than artemether with blood concentration rapid decreasing after intravenous injection. Its T1/2 is about 30 min. It is widely distributed in the body with the content in intestine, liver, kidney being relative high. Urine and fecal excretion account for only a small fraction. It mainly undergoes metabolic conversion. It is clinically suitable for rescue of critically ill patients with acute malaria and can be used as the first-choice drug for the treatment of patients with cerebral malaria and a variety of dangerous malaria. But its shortcoming is the recrudescence rate. No adverse reactions have been observed at the recommended therapeutic dose; the application of large doses may cause a transient reduction of the outer peripheral reticulocyte which will return to normal level after stopping drug. Women within 2 months of pregnancy should be disabled. Whether it will cause teratogenicity demands further study.

Dosage and administration

Powder: 60mg; each artesunate is also attached with one 5% sodium bicarbonate injection. Upon application, first dissolve the drug in sodium bicarbonate injection, and then diluted to 10 ml with glucose injection after intravenous infusion at a rate of 3~4ml/min. For the treatment of patients of chloroquine-resistant falciparum malaria: 60 mg per time with the first dose being doubled; intravenously inject 1 times per day with 4 days as a course of treatment. The total dose is 300mg. When the symptom gets controlled, you can change with other anti-malarial drugs to reduce the recrudescence rate. The exact dosage and tablets should be according to the exact condition.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Clinical application

The clinical application of artesunate has been as long as ten years. It is made through using the artemisia annua grass which is unique in China as raw material for extracting the active ingredient artemisinin and further going through chemical synthesis. Its major role is in treating plasmodia asexual form. It is also currently the only artemisinin derivatives which can be made into water-soluble formulation. It can be used to kill the parasite in inner phase of red blood cells to achieve the anti-malarial effect, and therefore being used in patients with various types of malaria, especially for treating and saving the patients with anti-chloroquine and anti-piperaquine falciparum malaria and severe-type cerebral malaria. It is characterized by high anti-malarial activity, high rate of fever abatement, short parasite clearance time and low drug toxic and side effects. It is the first-choice of drugs for the treatment of severe malaria.
For the application of artesunate tablets, using a total amount of 0.28 g in 3d course of treatment and a total amount of 0.44 g in 5d course of treatment, wherein applying the total amount 0.44 g (equivalent to 8.8 mg/kg) in 5d course for treatment of falciparum malaria can lead to the protozoa recrudescence rate being as low as 4.4% after clinical curing of the patients with no significant toxicity and side effect and no decline in reticulocytes, clarifying that the patients have good tolerance on this dose. Oral administration has low toxicity and rapid efficacy and is more convenient and simple for applying.
Applying 0.24 g/kg of artesunate for treatment of 72 cases of chloroquine-resistant falciparum malaria results in both the cooling time and asexual parasite clearance time being within 36 h and severely sicken patients being clinically cured. This clarifies that artesunate injection has many advantages including rapid insecticidal effect, short-term efficacy, safety, etc., it is suitable for the treatment and saving of patients with severe chloroquine-resistant falciparum malaria.

Uses

Artesunate is a kind of anti-malarial drug that has a relative strong killing effect on the asexual body of plasmodium falciparum and can result in rapid control of malaria episodes.
Artesunate is dispensed as a powder of artesunic acid. This is dissolved in sodium bicarbonate (5%) to form sodium artesunate. The solution is then diluted in approximately 5 ml of 5% dextrose and given by intravenous injection or by intramuscular injection to the anterior thigh. The solution should be prepared freshly for each administration and should not be stored.

Chemical Properties

Artesunate is an odorless bitter-tasting crystalline powder. soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of artesunate in these solvents is approximately 20, 14, and 11 mg/ml, respectively. Artesunate is sparingly soluble in aqueous buffers.

Uses

Artesunate, a semi-synthetic artemisinin derivative, has been shown to be effective against parasites, such as liver flukes, and has also shown cytotoxic effects on different types of tumor cell lines. artesunate belong to Antimalarial which is clinically useful for treatment of malaria and other parasitic diseases.

Definition

ChEBI: Artesunate is an artemisinin derivative that is the hemisuccinate ester of the lactol resulting from the reduction of the lactone carbonyl group of artemisinin. It is used, generally as the sodium salt, for the treatment of malaria. It has a role as an antimalarial, a ferroptosis inducer and an antineoplastic agent. It is an artemisinin derivative, a sesquiterpenoid, a dicarboxylic acid monoester, a cyclic acetal, a semisynthetic derivative and a hemisuccinate.

Preparation

Artemisinin was discovered in the 1970s as a result of an extensive screening of Chinese herbal extracts in the search of new antimalarial agents. Currently, the primary method for the production of artemisinin is the isolation from dried leaves of the plant Artemisia annua. Furthermore, the global supply of this life-saving drug exclusively from natural sources remains highly limited. As a result, a novel approaches for large-scale production of artemisinin have been developed. Artesunate is prepared from dihydroartemisinin (DHA) by reacting it with succinic acid anhydride in a basic medium.

A simplified and scalable synthesis of artesunate

brand name

Arsumax (Knoll, Switzerland).

General Description

Artesunate is a semisynthetic derivative of artemisinin used to treat malaria. It has also been shown to effective against other parasites such as liver flukes. Artesunate also demonstrates cytotoxic action against cancer cell lines of different tumor types.

Biochem/physiol Actions

Artesunate acts on the electron transport chain, generates local reactive oxygen species, and causes the depolarization of the mitochondrial membrane. It inhibits TNFα-induced production of proinflammatory cytokines via inhibition of NF-κB and PI3 kinase/Akt signal pathway in human rheumatoid arthritis fibroblast-like synoviocytes.

target

NF-kB | p38MAPK | IFN-γ | IL Receptor | PGE | COX | TNF-α | IkB | TGF-β/Smad | gp120/CD4 | Antifection | IKK

storage

Store at -20°C

Mode of action

Artesunate is a water-soluble, semi-synthetic derivative of the sesquiterpine lactone artemisinin with anti-malarial, anti-schistosomiasis, antiviral, and potential anti-neoplastic activities. It acts on the electron transport chain to generate local reactive oxygen species and cause depolarization of the mitochondrial membrane. It inhibits TNF-induced proinflammatory cytokine production by inhibiting NF-κB and PI3 kinase/Akt signaling pathways in human rheumatoid arthritis fibroblast-like synoviocytes. Artesunate has also been shown to stimulate cell differentiation, arrest the cell cycle in the G1 and G2/M phases, inhibit cell proliferation, and induce apoptosis through mitochondrial and caspase signaling pathways. Artemisinin is isolated from the plant Artemisia annua.

Artesunate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Artesunate manufacturers

Wuhan Haorong Biotechnology Co.,Ltd
Product
Artesunate 88495-63-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5000
Release date
2023-08-07
Hebei Yanxi Chemical Co., Ltd.
Product
Artesunate 88495-63-0
Price
US $40.00-40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-10-09
Shaanxi Haibo Biotechnology Co., Ltd
Product
Artesunate 88495-63-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000 Mt/Year
Release date
2023-12-05

88495-63-0, ArtesunateRelated Search:


  • ARTENSUNATE
  • Butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester
  • Artesunate (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol hydrogen succinate
  • ARTESUNATE
  • ArtesunateC19H28O8
  • Artemisinin monosuccinate
  • Artesunic Acid
  • Butanedioic Acid Mono(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] Ester
  • Arteannuinum
  • Arteannuinum succinate
  • (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol hydrogen succinate
  • vARTESUNATE
  • (3R,5aα,8aα,12aR)-Decahydro-10α-(3-carboxypropionyloxy)-3,6α,9β-trimethyl-3β,12α-epoxypyrano[4,3-j]-1,2-benzodioxepin
  • Succinic acid 1-[(3R,12aR)-3,6α,9β-trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydropyrano[4,3-j]-1,2-benzodioxepin-10α-yl] ester
  • WR-256283
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  • ARTESUTE
  • 4-Oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid
  • (91487-94-4) artesunate
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  • Artesunate &gt
  • Artesunate Artesunate
  • 4-Oxo-4-(((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid
  • Artesunate USP/EP/BP
  • Artesunate 13CD4
  • ArtesunateQ: What is Artesunate Q: What is the CAS Number of Artesunate Q: What is the storage condition of Artesunate Q: What are the applications of Artesunate
  • Artesunate (1042850)
  • Virus Protease,inhibit,Parasite,Artesunate,Inhibitor,Ferroptosis,STAT
  • 88495-63-0
  • 88475-63-0
  • 88495-60-0
  • C19H28O8
  • natural product
  • Antimalarial
  • Inhibitors
  • Herb extract
  • plant extract
  • Natural Plant Extract
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Active Pharmaceutical Ingredients
  • 88495-63-0