Artemisinin

HCID 68827CAS 119241-68-8

基本情報

標準SMILES: C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4
InChIKey: BLUAFEHZUWYNDE-NNWCWBAJSA-N
分子式: C15H22O5
平均分子量: 282.33 g/mol

概要

(+)-artemisinin is 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. It has a role as an antimalarial and a plant metabolite. It is an organic peroxide and a sesquiterpene lactone.

名称と識別子

優先名称: Artemisinin
IUPAC: (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

名称と別名

artemisinin63968-64-9QinghaosuHuanghuahaosu(+)-ArtemisininArtemisinineArtemisininumArtemisininaquinghaosuDTXSID2040652GNF-Pf-53419RMU91N5K2

名称をさらに表示

CHEBI:223316(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-oneNSC-369397DTXCID40819890qing hao su2-azanyl-5-methylsulfanyl-pentanoic acid1,5,9-trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo(10.3.1.04,13.08,13)hexadecan-10-one

データベース識別子

CAS: 119241-68-8、63968-64-9
PubChem CID: 68827
DTXSID: DTXSID2040652
ChEMBL: CHEMBL269671
ChEBI: CHEBI:223316
UNII: 9RMU91N5K2
EC Number: 700-290-5
Nikkaji: J86.051D

物性

構造計算による物性

XLogP: 2.8
極性表面積: 54 Å²
水素結合供与体数: 0
水素結合受容体数: 5
回転可能結合数: 0
重原子数: 20
形式電荷: 0
複雑度: 452

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]

LogP2.9

Collision Cross Section · 2 件

168.1 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

167.28 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 5.6% (2 of 36) of reports.

Danger

H242 (91.7%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]

P210, P234, P235, P240, P273, P280, P370+P378, P391, P403, P410, P411, P420, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 36 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationStatus: Active Update: 15-11-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1057

Hazard Classes and CategoriesOrg. Perox. D (91.7%)

毒性情報

Toxicity Summary · 1 件

A 2025 systematic review notes that although Artemisinin is generally regarded as being well-tolerated, ico-administration with other pharmacological agents should be carefully monitored. In animal-focused studies, Artemisinin led to neurotoxicity (affecting brain matter and nuclei), cardiotoxicity (slower heart rate and prolonged QTc interval), hematotoxicity (low counts of white blood cells and platelets), and genotoxicity, embryotoxicity, and nephrotoxicity.

Drug Induced Liver Injury · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Artemisinin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

化学と産業

薬理情報

ATC CodeP - Antiparasitic products, insecticides and repellents

Mechanism of ActionA 2025 systematic review notes that Artemisinin decreases lipid accumulation in hepatocytes by inhibiting CD36 expression and reducing TAG content.

MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.