U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22O5
Molecular Weight 282.3328
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTEMISININ

SMILES

C[C@]1([H])CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@@]3([H])[C@]42[C@@]1([H])CC[C@](C)(O3)OO4

InChI

InChIKey=BLUAFEHZUWYNDE-NNWCWBAJSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H22O5
Molecular Weight 282.3328
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/27006895

Artemisinin is a drug used to treat multi-drug resistant strains of falciparum malaria. The compound (a sesquiterpene lactone) is isolated from the plant Artemisia annua. Not all plants of this species contain artemisinin. Apparently it is only produced when the plant is subjected to certain conditions, most likely biotic or abiotic stress. It can be synthesized from artemisinic acid. It was discovered by Tu Youyou, a Chinese scientist, who was awarded half of the 2015 Nobel Prize in Medicine for this discovery. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. Artemisinin is also under early research and testing for treatment of cancer, primarily by researchers at the University of Washington. Artemisinin has a peroxide lactone group in its structure. It is thought that when the peroxide comes into contact with high iron concentrations (common in cancerous cells), the molecule becomes unstable and releases reactive oxygen species. It has been shown to reduce angiogenesis and the expression of vascular endothelial growth factor in some tissue cultures. The mechanism of action of arteminisin is not known, but the most widely accepted theory was 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. In 2016 artemisinin was shown to bind to a large number of targets suggesting that it acts in a promiscuous manner.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
24 nM [IC50]
Target ID: PfATP6, Plasmodium falciparum
79 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Artemisinin

Approved Use

Treatment of uncomplicated falciparum malaria in areas where there is evidence that chloroquine, pyrimethamine/sulfadoxine, mefloquine and quinine are ineffective. It should always be administered together with mefloquine in full therapeutic dose.

Launch Date

473299200000
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of artesunate after single oral administration to rats.
2001
Antiparasitic properties of medicinal plants and other naturally occurring products.
2001
Gas concentration effects on secondary metabolite production by plant cell cultures.
2001
Pharmacokinetic interactions of antimalarial agents.
2001
Severe falciparum malaria in five soldiers from East Timor: a case series and literature review.
2001 Aug
Artemisinin and derivatives: the future for malaria treatment?
2001 Dec
In vivo-in vitro model for the assessment of clinically relevant antimalarial cross-resistance.
2001 Dec
Artemisinin for treatment of uncomplicated falciparum malaria: is there a place for monotherapy?
2001 Dec
Current progress in the development and use of artemether for chemoprophylaxis of major human schistosome parasites.
2001 Dec
New trends in extraction, identification and quantification of artemisinin and its derivatives.
2001 Dec
Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action.
2001 Dec
The genetics of artemisinin content in Artemisia annua L. and the breeding of high yielding cultivars.
2001 Dec
Redox reaction of artemisinin with ferrous and ferric ions in aqueous buffer.
2001 Dec
Authentication of artemether, artesunate and dihydroartemisinin antimalarial tablets using a simple colorimetric method.
2001 Dec
C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene.
2001 Dec 20
Drug resistant falciparum malaria: clinical consequences and strategies for prevention.
2001 Jun
Effects of matrine, artemisinin, tetrandrine on cytosolic [Ca2+]i in guinea pig ventricular myocytes.
2001 Jun
Total synthesis of (+)-arteanniun M using the tandem oxy-Cope/ene reaction.
2001 Jun 14
New manzamine alkaloids with potent activity against infectious diseases.
2001 Mar 7
Artemisinin and its derivatives: an important new class of antimalarial agents.
2001 May-Jun
Resistance of Plasmodium falciparum to antimalarial drugs in a highly endemic area of southern Viet Nam: a study in vivo and in vitro.
2001 May-Jun
Chlorproguanil-dapsone (LAPDAP) for uncomplicated falciparum malaria.
2001 Nov
Controlling malaria: challenges and solutions.
2001 Nov
Artesunate and praziquantel for the treatment of Schistosoma haematobium infections: a double-blind, randomized, placebo-controlled study.
2001 Nov 15
Selective toxicity of dihydroartemisinin and holotransferrin toward human breast cancer cells.
2001 Nov 21
'To search and studdy out the secrett of tropical diseases by way of experiment'.
2001 Nov-Dec
Improved oral bioavailability of artemisinin through inclusion complexation with beta- and gamma-cyclodextrins.
2001 Oct 4
[Prevention and treatment of malaria: in vitro evaluation of new compounds].
2001 Sep
Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity.
2001 Sep
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand.
2001 Sep 1
Combination therapy for malaria: the way forward?
2002
Effect of antimalarial drugs on plasmodia cell-free protein synthesis.
2002 Apr
Epidemiology of drug-resistant malaria.
2002 Apr
Efficacy of artesunate and praziquantel in Schistosoma haematobium infected schoolchildren.
2002 Apr
Anhydrodihydroartemisinin and its 10-trifluoromethyl analogue: access to novel d-ring-contracted artemisinin trifluoromethyl ketones.
2002 Feb 22
Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues.
2002 Feb 28
Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model.
2002 Feb 8
Plasmodium falciparum: in vitro interactions of artemisinin with amodiaquine, pyronaridine, and chloroquine.
2002 Jan
Structure-activity relationships of the antimalarial agent artemisinin. 6. The development of predictive in vitro potency models using CoMFA and HQSAR methodologies.
2002 Jan 17
Assessment of the neurotoxicity of oral dihydroartemisinin in mice.
2002 Jan-Feb
Development and validation of a high-performance liquid chromatography-mass spectrometry assay for the determination of artemether and its metabolite dihydroartemisinin in human plasma.
2002 Jul 15
Antiulcerogenic activity of some sesquiterpene lactones isolated from Artemisia annua.
2002 Jun
From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs.
2002 Mar
Inhibition of nitric oxide-dependent activation of soluble guanylyl cyclase by the antimalarial drug, artemisinin.
2002 Mar 1
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement?
2002 Mar 25
First synthesis of 10 alpha-(trifluoromethyl)deoxoartemisinin.
2002 Mar 7
Activity of drugs from traditional Chinese medicine toward sensitive and MDR1- or MRP1-overexpressing multidrug-resistant human CCRF-CEM leukemia cells.
2002 Mar-Apr
Recent investigations of artemether, a novel agent for the prevention of schistosomiasis japonica, mansoni and haematobia.
2002 May
How might qinghaosu (artemisinin) and related compounds kill the intraerythrocytic malaria parasite? A chemist's view.
2002 May
Central role of the spleen in malaria parasite clearance.
2002 May 15
Patents

Sample Use Guides

Adults and children: 25 mg/kg on the first day followed by 12.5 mg/kg on the second and third days in combination with mefloquine (15 mg/kg) in a single dose on the second day. In some areas, a higher dose (25 mg/kg) of mefloquine may be required for a cure to be obtained.
Route of Administration: Oral
In Vitro Use Guide
Artemisinine was active against 3 chloroquine-resistant strains of Plasmodium falciparum, strains K1 and T996 from Thailand and LS21 from India, with complete growth inhibition at 10(-7) M.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:36:41 UTC 2021
Edited
by admin
on Sat Jun 26 15:36:41 UTC 2021
Record UNII
9RMU91N5K2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEMISININ
INCI   INN   MART.   MI   USP-RS   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
QING HAU SAU
Common Name English
GNF-PF-5341
Code English
ARTEMISININUM [WHO-IP LATIN]
Common Name English
ARTEMISININ [MART.]
Common Name English
HUANGHUAHAOSU
Common Name English
ARTEMISININ [INN]
Common Name English
ARTEMISININ [INCI]
Common Name English
ARTEMISININ [WHO-IP]
Common Name English
NSC-369397
Code English
ARTEMISININ [WHO-DD]
Common Name English
ARTEMISININ [MI]
Common Name English
ARTEMISININ [USP-RS]
Common Name English
(3R,5AS,6R,8AS,9R,12S,12AR)-3,6,9-TRIMETHYLOCTAHYDRO-3,12-EPOXYPYRANO(4,3-J )-1,2-BENZODIOXEPIN-10(3H)-ONE
Systematic Name English
(3R,5AS,6R,8AS,9R,12S,12AR)-OCTAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10(3H)-ONE
Common Name English
Classification Tree Code System Code
DSLD 2508 (Number of products:21)
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
LIVERTOX 64
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
WHO-ATC P01BE01
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
NCI_THESAURUS C277
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
ARTEMISININ
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY Description: Colourless needles or white crystalline powder. Solubility: Practically insoluble in water; very soluble in dichloromethane R; freely soluble in acetone R and ethyl acetate R; soluble in glacial acetic acid R, methanol R and ethanol (~750 g/L) TS. Category: Antimalarial. Storage: Artemisinin should be kept in a well-closed container and protected from light. Requirement: Artemisinin contains not less than 97.0% and not more than 102.0% of C15H22O5, calculated with reference to the dried substance.
EPA CompTox
63968-64-9
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
DRUG CENTRAL
3871
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
RXCUI
2367409
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
DRUG BANK
DB13132
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
NCI_THESAURUS
C78093
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
MESH
C031327
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
INN
5954
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
WIKIPEDIA
ARTEMISININ
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
CAS
63968-64-9
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
MERCK INDEX
M2077
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY Merck Index
FDA UNII
9RMU91N5K2
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
PUBCHEM
68827
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
USP_CATALOG
1042747
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY USP-RS
EVMPD
SUB05575MIG
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL567597
Created by admin on Sat Jun 26 15:36:42 UTC 2021 , Edited by admin on Sat Jun 26 15:36:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
PARENT -> IMPURITY
In the chromatogram obtained with solution (1): the area of any peak corresponding to impurity B (artemisinin) is not greater than 0.5 times the area of the principal peak obtained with solution (4) (0.5%).
CHROMATOGRAPHIC PURITY (HPLC/UV)
IMPURITY -> PARENT
IMPURITY -> PARENT