.ALPHA.-DIHYDROARTEMISININ

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H24O5
Molecular Weight	284.3481
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](O)[C@@H]2C)O4

InChI

InChIKey=BJDCWCLMFKKGEE-KDTBHNEXSA-N

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

HIDE SMILES / InChI

Description

Sodium artesunate, an artemisinin derivative, is used in malaria treatment. Artesunate, has been licensed in Thailand for the treatment of falciparum malaria since 1990. It is a potent antimalarial drug that can reduce parasitaemia by 90% within 24 h of administration. Sodium artesunate was first isolated in China, it is a water soluble antimalaria used clinically in China.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Pneumocystis carinii 4	Inhibitor 8,297
Sodium/potassium-transporting ATPase subunit alpha-1 16	Inhibitor 8,297
Plasmodium falciparum 74	Inhibitor 8,297	4.1 nM [IC50]
Plasmodium yoelii 3	Inhibitor 8,297
Plasmodium berghei 9	Inhibitor 8,297
Plasmodium falciparum 74	Inhibitor 8,297
DNA 278	Binding Agent 1,064
DNA 278	Binding Agent 1,064
Plasmodium falciparum 74	Binding Agent 1,064

Conditions

Condition	Modality	Highest Phase	Product
Plasmodium falciparum malaria 63	Primary	Approved 8,429	Sodium artesunate
Plasmodium falciparum malaria 63	Curative	Approved 8,429	Eurartesim
Malaria 95	Curative	Approved 8,429	Unknown
Schistosoma mansoni infection 8	Curative	Phase III 656	Unknown
Colorectal cancer 101	Primary	Phase II 1,132	Unknown
Cervical cancer 40	Primary	Phase I 428	Unknown
Hepatocellular carcinoma 83	Primary	Phase I 428	Unknown
Breast cancer 434	Primary	Phase I 428	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 μg/mL	2.4 mg/kg multiple, intravenous		ARTENIMOL unknown	Homo sapiens
3.3 μg/mL	2.4 mg/kg multiple, intravenous		ARTESUNATE unknown	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
3.5 μg × h/mL	2.4 mg/kg multiple, intravenous		ARTENIMOL unknown	Homo sapiens
0.7 μg × h/mL	2.4 mg/kg multiple, intravenous		ARTESUNATE unknown	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.3 h	2.4 mg/kg multiple, intravenous		ARTENIMOL unknown	Homo sapiens
0.3 h	2.4 mg/kg multiple, intravenous		ARTESUNATE unknown	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
7%	2.4 mg/kg multiple, intravenous		ARTENIMOL unknown	Homo sapiens
7%	2.4 mg/kg multiple, intravenous		ARTESUNATE unknown	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
2.4 mg/kg 1 times / day multiple, intravenous (complex) Recommended	unhealthy, 1-72 years n = 92	Other AEs: Anemia, Transaminases increased...
100 mg 1 times / day multiple, oral Studied dose	unhealthy, 15-35 years n = 31	Other AEs: Nausea, Dizziness...
2.4 mg/kg 1 times / day multiple, intravenous\|oral (complex) Recommended	unhealthy, 2-87 years n = 730	Other AEs: Acute renal failure, Hemoglobinuria...
25 mg/kg 2 times / 3 weeks multiple, intravenous Highest studied dose	unhealthy, 58 years n = 2	DLT: Nausea, Vomiting...
18 mg/kg 2 times / 3 weeks multiple, intravenous MTD	unhealthy, 58 years n = 6	DLT: Hypersensitivity reaction...

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AEs

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AE	Significance	Dose	Population
Acute renal failure	10%	2.4 mg/kg 1 times / day multiple, intravenous (complex) Recommended	unhealthy, 1-72 years n = 92
Leukocytosis	10%	2.4 mg/kg 1 times / day multiple, intravenous (complex) Recommended	unhealthy, 1-72 years n = 92
Hyperbilirubinemia	14%	2.4 mg/kg 1 times / day multiple, intravenous (complex) Recommended	unhealthy, 1-72 years n = 92
Thrombocytopenia	18%	2.4 mg/kg 1 times / day multiple, intravenous (complex) Recommended	unhealthy, 1-72 years n = 92
Transaminases increased	27%	2.4 mg/kg 1 times / day multiple, intravenous (complex) Recommended	unhealthy, 1-72 years n = 92

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 CYP2C19 1,478 CYP3A4/5 278 CYP1A2 1,524	UGT1A9 380 UGT2B7 389 P-gp 1,537	CYP2A6 79 CYP3A 129

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite
CYP1A2 1,692	inhibitor 3,277	no [IC50 >100 uM]
CYP2B6 1,001	inhibitor 3,277	no [IC50 >100 uM]
CYP2B6 1,001	inhibitor 3,277	no [IC50 >100 uM]	DHA 3
CYP2C19 1,553	inhibitor 3,277	no [IC50 >100 uM]
CYP2C9 1,819	inhibitor 3,277	no [IC50 >100 uM]

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Drug as victim

Show entries

Target	Modality	Activity	Metabolite
P-gp 1,537	substrate 3,367	no	DHA 3
UGT1A9 380	substrate 3,367	yes	DHA 3
UGT2B7 389	substrate 3,367	yes	DHA 3

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626		DHA 3

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63918	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63918
MolPort	MolPort-006-392-384	https://www.molport.com/shop/molecule-link/MolPort-006-392-384
ZINC	ZINC000014096305	http://zinc15.docking.org/substances/ZINC000014096305
eMolecules	1935656	https://www.emolecules.com/cgi-bin/more?vid=1935656
eMolecules	29933844	https://www.emolecules.com/cgi-bin/more?vid=29933844

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PubMed

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Title	Date	PubMed
[Effects of sodium artesunate on electrical properties and Na+,K(+)-ATPase activities of mouse small intestine].	1990 Jul	1966574
Monotherapy with sodium artesunate for uncomplicated falciparum malaria in Thailand: a comparison of 5- and 7-day regimens.	1997 Sep 30	9241384
Artesunate and mefloquine given simultaneously for three days via a prepacked blister is equally effective and tolerated as a standard sequential treatment of uncomplicated acute Plasmodium falciparum malaria: randomized, double-blind study in Thailand.	2002 Nov	12479545
Randomized control trial of quinine and artesunate in complicated malaria.	2004 Apr	15107507
Adding artesunate to sulphadoxine-pyrimethamine greatly improves the treatment efficacy in children with uncomplicated falciparum malaria on the coast of Benin, West Africa.	2007 Dec 21	18154655

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Patents

Sample Use Guides

In Vivo Use Guide

Artesunate can be used orally, by intravenous or intramuscular injection or as a suppository. As an injection, artesunate 2.4mg/kg bw i.v or i.m. given on admission (time =0), then at 12hr and 24hr, then once a day.

Route of Administration: Other

In Vitro Use Guide

An artemisinin concentration of 100-300 nM in vitro caused swelling of the endoplasmic reticulum and mitochondria, as well as injuries both to the limiting and to the nuclear membranes of chloroquine-resistant P. falciparum (ItG2 strain) within 2 h.

Show entries

Name

Type

Language

.ALPHA.-DIHYDROARTEMISININ

Common Name

English

DIHYDROARTIMISININ

Common Name

English

3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-OL, DECAHYDRO-3,6,9-TRIMETHYL-, (3R,5AS,6R,8AS,9R,10R,12R,12AR)-

Common Name

English

3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-OL, DECAHYDRO-3,6,9-TRIMETHYL-, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-

Common Name

English

NSC-758682

Code

English

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Code System

Code

Type

Description

CAS

81496-81-3

PRIMARY

DRUG BANK

DBMET00793

PRIMARY

PUBCHEM

11358077

PRIMARY

FDA UNII

X0UIV26ABX

PRIMARY

RXCUI

2584841

PRIMARY

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PARENT (METABOLITE)


					C7D6T3H22J

ARTEMETHER

PRODRUG (METABOLITE ACTIVE)


					60W3249T9M

ARTESUNATE

SUBSTANCE RECORD


					X0UIV26ABX

.ALPHA.-DIHYDROARTEMISININ

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator