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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:135921
CAS Number: 71939-50-9
TTD ID: D0N6FH
INTEDE ID: DR0142

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]

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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]

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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]
Annexin A2 (ANXA2)	OTFNS0CC	ANXA2_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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.