NAV

Artemisinin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Artemisinin is 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
3D
Similar Structures
Weight
Average: 282.336
Monoisotopic: 282.146723808
Chemical Formula
C15H22O5
Synonyms
  • Artemisinin
  • artemisinina
External IDs
  • NSC-369397
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatMalaria caused by plasmodium falciparumCombination Product in combination with: Piperaquine (DB13941)••••••••••••••••••• •••• ••••••
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/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without 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.
DrugInteraction
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interactions in your software
AbametapirThe serum concentration of Artemisinin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Artemisinin can be increased when combined with Abatacept.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Artemisinin is combined with Acetophenazine.
AdalimumabThe metabolism of Artemisinin can be increased when combined with Adalimumab.
AlimemazineThe risk or severity of QTc prolongation can be increased when Artemisinin is combined with Alimemazine.
Food Interactions
Not Available

Products

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Categories

ATC Codes
P01BF08 — Artemisinin and naphthoquineP01BF07 — Artemisinin and piperaquineP01BE01 — Artemisinin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentMalaria caused by Plasmodium falciparum / Plasmodium Falciparum1
3CompletedTreatmentSchizophrenia1
2Active Not RecruitingTreatmentAIN2/3 / Anal High-Grade Squamous Intraepithelial Lesions / Anal Intraepithelial Neoplasia (AIN) / Anal Precancerous Condition / Human Papilloma Virus (HPV)1
2Not Yet RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19)1
2RecruitingTreatmentAnal High-Grade Squamous Intraepithelial Lesions / Anal HPV Infection / Anal HSIL1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.27 mg/mLALOGPS
logP2.52ALOGPS
logP3.11Chemaxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area53.99 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity68.68 m3·mol-1Chemaxon
Polarizability29.43 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0007-0901000000-4fa10fe72dc24b85ac9c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0190000000-3391c971e951545100ee
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ldj-0960000000-ff3a9e18db5c8c53bcb4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01wb-0910000000-42c2b516c8462b3dd492
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01x1-0900000000-5c3e44b5d52be3adbba2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a7l-0900000000-01583256dc6d13c1315f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a59-0900000000-189290ae52e9283563ba
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-d3e040716e12d73b70aa
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-2e7c32333f0d5125e77b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0090000000-40b53fa8a77f4e3350da
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1090000000-b8cdd22141f94171ca25
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-14e0d7ed35ed5494117d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-2090000000-ddbd5456f2d606740d6a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.5460604
predicted
DarkChem Lite v0.1.0
[M-H]-166.4608604
predicted
DarkChem Lite v0.1.0
[M-H]-160.9841
predicted
DeepCCS 1.0 (2019)
[M+H]+166.2310604
predicted
DarkChem Lite v0.1.0
[M+H]+166.9595604
predicted
DarkChem Lite v0.1.0
[M+H]+162.8929
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.9450604
predicted
DarkChem Lite v0.1.0
[M+Na]+166.5740604
predicted
DarkChem Lite v0.1.0
[M+Na]+168.67989
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 2B6
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
Cytochrome P450 2B6
Molecular Weight
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