Artesunato

Base Information

• Chemical Name: Artesunato
• CAS No.: 88495-63-0
• Molecular Formula: C19H28O8
• Molecular Weight: 384.427
• Hs Code.: 29419090
• European Community (EC) Number: 605-980-9,618-170-5
• NSC Number: 712571
• Wikipedia: Artesunate
• NCI Thesaurus Code: C73005
• Metabolomics Workbench ID: 125856
• ChEMBL ID: CHEMBL1967249
• Mol file: 88495-63-0.mol

Synonyms:artesunic acid

Chemical Property of Artesunato

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 132-135 °C
• Refractive Index: 1.543
• Boiling Point: 502.1 °C at 760 mmHg
• PKA: 4.28±0.17(Predicted)
• Flash Point: 173.5 °C
• PSA: 100.52000
• Density: 1.31 g/cm³
• LogP: 2.60240
• Storage Temp.: Room temp
• Solubility.: acetone: soluble33.4mg/mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 384.17841785
• Heavy Atom Count: 27
• Complexity: 623

Purity/Quality:

99.5%, ^*data from raw suppliers

Artesunate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC(=O)CCC(=O)O)C
• Recent ClinicalTrials: Artesunate Suppositories for the Treatment of HIV-negative Patients With Intra-anal HSIL
• Recent EU Clinical Trials: PHASE I-II EFFICACY-TOXICITY OF ARTESUNATE IN FRIEDREICH ATAXIA
• 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. 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.

Technology Process of Artesunato

There total 10 articles about Artesunato which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

succinic acid anhydride (108-30-5) + dihydroartesiminin (81496-81-3) → artesunate (88495-63-0)

Guidance literature:

With dmap; In 1,2-dichloro-ethane; at 45 ℃; for 6h; Reagent/catalyst; Solvent; Temperature; Industrial scale;

Reference yield: 96.0%

succinic acid anhydride (108-30-5) + C12H13O2(CH3)3(O)(OO) (63968-64-9) → artesunate (88495-63-0)

Guidance literature:

C₁₂H₁₃O₂(CH₃)3(O)(OO); With sodium tetrahydroborate; cation exchange resin; In tetrahydrofuran; at 20 - 35 ℃; for 0.666667h;

succinic acid anhydride; With triethylamine; In tetrahydrofuran; at 20 - 35 ℃; for 1h;

Reference yield: 94.0%

succinic acid anhydride (108-30-5) + dihydroartemisinin (71939-50-9) → artesunic acid (88495-63-0)

Guidance literature:

With triethylamine; In Isopropyl acetate; at 20 ℃; for 4.5h; Temperature; Inert atmosphere; Green chemistry;

DOI:10.1007/s00706-016-1865-9

upstream raw materials:

succinic acid anhydride

dihydroartesiminin

dihydroartemisinin

dihydroartemisinin

Refernces

• 1、 -. "Tetravalent platinum complex containing artesunate as well as preparation method and application of tetravalent platinum complex". Paragraph 0045; 0049; 0050. . Retrieved 2021/07/08.
• 2、 Chen, Xuemei,Huang, Pei,Wang, Jing,Tian, Runmei,Chen, Yan,Chen, Yongzheng,Zhang, Lei,Ma, Zhigui. "Identification of H2S/NO-donating artemisinin derivatives as potential antileukemic agents". . p. 501 - 511. Retrieved 2020/01/13.