This drug entry is astuband has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Artemisininis a medication indicated in the treatment of malaria.

Generic Name
Artemisinin
DrugBank Accession Number
DB13132
Background

Artemisinin has been used in trials studying the treatment of Schizophrenia, Malaria, Falciparum, and Plasmodium Falciparum.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 282.336
Monoisotopic: 282.146723808
Chemical Formula
C15H22O5
Synonyms
  • Artemisinin
  • artemisinina
External IDs
  • NSC-369397

Pharmacology

Indication

Not Available

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
这些信息不应该被解释the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
Abametapir The serum concentration of Artemisinin can be increased when it is combined with Abametapir.
Abatacept The metabolism of Artemisinin can be increased when combined with Abatacept.
Acetophenazine The risk or severity of QTc prolongation can be increased when Artemisinin is combined with Acetophenazine.
Adalimumab The metabolism of Artemisinin can be increased when combined with Adalimumab.
Alimemazine The risk or severity of QTc prolongation can be increased when Artemisinin is combined with Alimemazine.
Alpelisib The metabolism of Artemisinin can be increased when combined with Alpelisib.
Amitriptyline The metabolism of Artemisinin can be decreased when combined with Amitriptyline.
Amprenavir The metabolism of Artemisinin can be decreased when combined with Amprenavir.
Anakinra The metabolism of Artemisinin can be increased when combined with Anakinra.
Antipyrine The metabolism of Artemisinin can be decreased when combined with Antipyrine.
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Food Interactions
Not Available

Products

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Categories

ATC Codes
P01BF08 — Artemisinin and naphthoquine P01BF07 — Artemisinin and piperaquine P01BE01 — Artemisinin
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Terpene lactones
Direct Parent
Terpene lactones
Alternative Parents
Artemisinins/Oxepanes/Delta valerolactones/Trioxanes/Oxanes/Dialkyl peroxides/Carboxylic acid esters/Oxacyclic compounds/Monocarboxylic acids and derivatives/Acetals
show 2 more
Substituents
1,2,4-trioxane/Acetal/Aliphatic heteropolycyclic compound/Artemisinin skeleton/Carbonyl group/Carboxylic acid derivative/Carboxylic acid ester/Delta valerolactone/Delta_valerolactone/Dialkyl peroxide
show 12 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
organic peroxide, sesquiterpene lactone (CHEBI:223316)/Eudesmane sesquiterpenoids, Sesquiterpenoids (C15) (C09538)/Eudesmane sesquiterpenoids (LMPR0103190003)
Affected organisms
Not Available

Chemical Identifiers

UNII
9RMU91N5K2
CAS number
63968-64-9
InChI Key
BLUAFEHZUWYNDE-NNWCWBAJSA-N
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
IUPAC Name
(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
SMILES
[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4

References

General References
Not Available
KEGG Compound
C09538
PubChem Compound
68827
PubChem Substance
347829251
ChemSpider
62060
BindingDB
50088447
RxNav
2367409
ChEBI
223316
ChEMBL
CHEMBL269671
ZINC
ZINC000008143788
PharmGKB
PA165111696
Wikipedia
Artemisinin

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Completed Treatment Malaria caused by Plasmodium falciparum/Plasmodium Falciparum 1
3 Completed Treatment Schizophrenia 1
2 Not Yet Recruiting Treatment AIN 2/3/Anal High-Grade Squamous Intraepithelial Lesions/Anal Intraepithelial Neoplasia (AIN)/Anal Precancerous Condition/Human Papilloma Virus (HPV) 1
2 Not Yet Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) 1
2 Recruiting Treatment Cervical Dysplasia/CIN 2/3/HPV Related Diseases/Human Papilloma Virus (HPV)/Pre-Cancerous Dysplasia 1
2 Withdrawn Treatment Coronavirus Disease 2019 (COVID‑19)/CoVid 19积极/Infections, Coronavirus 1
2 Withdrawn Treatment Plasmodium Infections 1
1 Completed Treatment AIN2/3/Alternative Treatment/Anal Intraepithelial Neoplasia (AIN)/Artesunate/HPV-Related Anal Intraepithelial Neoplasia/Human Papilloma Virus (HPV)/Precancerous Conditions 1
Not Available Completed Screening Malaria, Asymptomatic Parasitaemia/Plasmodium Infections 1
Not Available Completed Treatment Plasmodium Infections 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Form Route Strength
Tablet, film coated Oral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
Property 价值 Source
Water Solubility 1.27 mg/mL ALOGPS
logP 2.52 ALOGPS
logP 3.11 ChemAxon
日志 -2.4 ALOGPS
pKa (Strongest Basic) -4.4 ChemAxon
Physiological Charge 0 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 53.99 Å2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 68.68 m3·mol-1 ChemAxon
Polarizability 29.43 Å3 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five Yes ChemAxon
Ghose Filter Yes ChemAxon
Veber's Rule No ChemAxon
MDDR-like Rule No ChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-014i-0190000000-3391c971e951545100ee
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-0ldj-0960000000-ff3a9e18db5c8c53bcb4
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-01wb-0910000000-42c2b516c8462b3dd492
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-01x1-0900000000-5c3e44b5d52be3adbba2
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-0a7l-0900000000-01583256dc6d13c1315f
MS/MS Spectrum - , positive LC-MS/MS splash10-0a59-0900000000-189290ae52e9283563ba

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
细胞色素P450 2B6
分子量
56277.81 Da
References
  1. Hedrich WD, Hassan HE, Wang H: Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. doi: 10.1016/j.apsb.2016.07.016. Epub 2016 Aug 9. [Article]
  2. Xing J, Kirby BJ, Whittington D, Wan Y, Goodlett DR: Evaluation of P450 inhibition and induction by artemisinin antimalarials in human liver microsomes and primary human hepatocytes. Drug Metab Dispos. 2012 Sep;40(9):1757-64. doi: 10.1124/dmd.112.045765. Epub 2012 Jun 7. [Article]
  3. Flockhart Table of Drug Interactions [Link]

Drug created at October 21, 2016 03:33 / Updated at June 12, 2021 10:55