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

Identification

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Name
Artemisinin
Accession Number
DB13132
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
  • Artemisinin
  • artemisinina
External IDs
NSC-369397
Categories
UNII
9RMU91N5K2
CAS number
63968-64-9
Weight
Average: 282.336
Monoisotopic: 282.146723808
Chemical Formula
C15H22O5
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
AbataceptThe metabolism of Artemisinin can be increased when combined with Abatacept.
AcepromazineThe risk or severity of QTc prolongation can be increased when Artemisinin is combined with Acepromazine.
AceprometazineThe risk or severity of QTc prolongation can be increased when Artemisinin is combined with Aceprometazine.
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.
AfelimomabThe metabolism of Artemisinin can be increased when combined with Afelimomab.
AlimemazineThe risk or severity of QTc prolongation can be increased when Artemisinin is combined with Alimemazine.
AlpelisibThe metabolism of Artemisinin can be increased when combined with Alpelisib.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Artemisinin.
AmlodipineThe metabolism of Artemisinin can be decreased when combined with Amlodipine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C09538
PubChem Compound
68827
PubChem Substance
347829251
ChemSpider
62060
BindingDB
50088447
ChEBI
223316
ChEMBL
CHEMBL269671
PharmGKB
PA165111696
Wikipedia
Artemisinin
ATC Codes
P01BE01 — Artemisinin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingTreatmentAIN2/3 / Alternative Treatment / Anal Intraepithelial Neoplasia (AIN) / Artesunate / HPV-Related Anal Intraepithelial Neoplasia / Human Papilloma Virus (HPV) / Precancerous Conditions1
2Not Yet RecruitingTreatmentCervical Dysplasia / CIN 2/3 / HPV Infections / Pre-Cancerous Dysplasia1
2Not Yet RecruitingTreatmentPlasmodium Infections1
3CompletedTreatmentSchizophrenic Disorders1
4CompletedTreatmentMalaria caused by Plasmodium falciparum / Plasmodium Falciparum1
Not AvailableCompletedScreeningMalaria, Asymptomatic Parasitaemia / Plasmodium Infections1
Not AvailableCompletedTreatmentPlasmodium Infections1
Not AvailableUnknown StatusNot AvailableParasitemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Artemisinin skeleton / Terpene lactone / Sesquiterpenoid / Delta valerolactone / Delta_valerolactone / Oxepane / Oxane / 1,2,4-trioxane / Carboxylic acid ester / Lactone
show 12 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
organic peroxide, sesquiterpene lactone (CHEBI:223316) / Eudesmane sesquiterpenoids, Sesquiterpenoids (C15) (C09538) / Eudesmane sesquiterpenoids (LMPR0103190003)

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
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. [PubMed:27709010]
  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. [PubMed:22679214]
  3. Flockhart Table of Drug Interactions [Link]

Drug created on October 20, 2016 21:33 / Updated on December 02, 2019 09:50