Details of the Drug

General Information of Drug (ID: DMBXVMZ)

Drug Name
Dihydroartemisinin
Synonyms
Artenimol; Cotecxin; Dihydroartemisinine; Dihydroqinghaosu; Dihydroquinghaosu; Dihydroquinghoasu; VM3352; Artenimol (INN); JAV-110; GNF-PF-5634; (3R,5aS,6R,8aS,9R,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10-ol; [3R-(3.alpha.,5a.beta.,6.beta.,8a.beta.,9.alpha.,10.alpha.,12.beta.,12aR*)]-Decahydro-10-hydroxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4.3-j]-1,2-benzodioxepin; 1,5,9-trimethyl-(1R,4S,5R,8S,9R,10S,12R,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol(Dihydroartemisinin)
Indication
Disease Entry ICD 11 Status REF
Malaria 1F40-1F45 Approved [1]
ATC Code
P01BE05: Dihydroartemisinin
P01BE: Artemisinin and derivatives, plain
P01B: ANTIMALARIALS
P01: ANTIPROTOZOALS
P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 284.35
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-2 h [2]
Bioavailability
The bioavailability of drug is 45% [2]
Clearance
The clearance of drug is 1.340 L/h/kg [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 1 hour []
Metabolism
The drug is metabolized via UGT1A9 [2]
Vd
The volume of distribution (Vd) of drug is 0.801 L/kg [2]
Chemical Identifiers
Formula
C15H24O5
IUPAC Name
(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
Canonical SMILES
C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)O)C
InChI
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
InChIKey
BJDCWCLMFKKGEE-ISOSDAIHSA-N
Cross-matching ID
PubChem CID
3000518
ChEBI ID
CHEMBL307261
CAS Number
71939-50-9
UNII
6A9O50735X
DrugBank ID
DB11638
TTD ID
D0N6FH
INTEDE ID
DR0142
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sarcoplasmic/endoplasmic reticulum calcium ATPase (ATP2A) TTZVSJ2 NOUNIPROTAC Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 2B7 (UGT2B7) DEB3CV1 UD2B7_HUMAN Substrate [3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, cytoplasmic 2 (ACTG1) OTH4V7VQ ACTG_HUMAN Protein Interaction/Cellular Processes [4]
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [4]
Alpha-aminoadipic semialdehyde dehydrogenase (ALDH7A1) OTV57BZD AL7A1_HUMAN Protein Interaction/Cellular Processes [4]
Alpha-enolase (ENO1) OTB1KWJS ENOA_HUMAN Protein Interaction/Cellular Processes [4]
Alpha-ketoglutarate-dependent dioxygenase FTO (FTO) OTXML85Y FTO_HUMAN Protein Interaction/Cellular Processes [4]
ATP synthase subunit alpha, mitochondrial (ATP5F1A) OT3FZDLX ATPA_HUMAN Protein Interaction/Cellular Processes [4]
ATP synthase subunit g, mitochondrial (ATP5MG) OTD569IJ ATP5L_HUMAN Protein Interaction/Cellular Processes [4]
ATP synthase subunit O, mitochondrial (ATP5PO) OTU3MCTN ATPO_HUMAN Protein Interaction/Cellular Processes [4]
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Gene/Protein Processing [5]
Calpastatin (CAST) OTBXZZGF ICAL_HUMAN Protein Interaction/Cellular Processes [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
2 EMA: Eurartesim Assessment Report
3 Eurartesim - European Medicines Agency
4 Untargeted Proteomics and Systems-Based Mechanistic Investigation of Artesunate in Human Bronchial Epithelial Cells. Chem Res Toxicol. 2015 Oct 19;28(10):1903-13. doi: 10.1021/acs.chemrestox.5b00105. Epub 2015 Sep 21.
5 Dihydroartemisinin protects against alcoholic liver injury through alleviating hepatocyte steatosis in a farnesoid X receptor-dependent manner. Toxicol Appl Pharmacol. 2017 Jan 15;315:23-34. doi: 10.1016/j.taap.2016.12.001. Epub 2016 Dec 6.