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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H28O5
Molecular Weight 312.4019
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTEMOTIL

SMILES

CCO[C@]1([H])[C@]([H])(C)[C@]2([H])CC[C@@]([H])(C)[C@]3([H])CC[C@]4(C)O[C@]([H])([C@@]32OO4)O1

InChI

InChIKey=NLYNIRQVMRLPIQ-XQLAAWPRSA-N
InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14+,15-,16-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H28O5
Molecular Weight 312.4019
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Artemotil (also known as beta-arteether) is an antimalarial artemisinin derivative, approved for the treatment of severe cases of P. falciparum malaria. The mixture of artemotil and alpha-arteether is used in patients with cerebral malaria. Most of the artemisinin compounds including artemotil are metabolized into dihydroartemisinin, which is responsible for antimalarial activity. These compounds contain stable endoperoxide bridge. The antimalarial activity of the drug thus is dependent on the cleavage of the endoperoxide by intraparasitic heme. The cleaved endoperoxide ultimately becomes a carbon centered free radical, which then functions as an alkylating agent, reacting with both heme and parasitic proteins (but not DNA). In P. falciparum, one of the principal alkylation target is the translationally controlled tumor protein (DHA-TCTP) homolog. Some intraparasitic TCTP is situated in the membrane surrounding the heme-rich food vacuole, where heme could catalyse the formation of drug-protein (DHA-TCTP) adduct and inhibit the parasite's growth.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q8I3Z5
Gene ID: 812831
Gene Symbol: TCTP
Target Organism: Plasmodium falciparum (isolate 3D7)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ARTECEF

Approved Use

Severe P. falciparum malaria infection.
PubMed

PubMed

TitleDatePubMed
Inhibition of growth of Toxoplasma gondii by qinghaosu and derivatives.
1990 Oct
In vitro effects of artemisinin ether, cycloguanil hydrochloride (alone and in combination with sulfadiazine), quinine sulfate, mefloquine, primaquine phosphate, trifluoperazine hydrochloride, and verapamil on Toxoplasma gondii.
1994 Jun
Bile acid-based 1,2,4-trioxanes: synthesis and antimalarial assessment.
2012 Dec 13
Patents

Sample Use Guides

The initial dose consists of an injection of 4.8 mg artemotil per kg body weight evenly divided over both anterior thighs. The follow-up doses consist of 1.6 mg per kg body weight after 6, 24, 48 and 72 hours in alternating thighs.
Route of Administration: Intramuscular
The microassay for minimum inhibitory concentrations (MICs) of arteether isomers, including artemotil, was carried out in 96-well microtitre plates against four inhouse maintained strains of P. falciparum (NF54, 3D7, RKL9 and JDP8) in vitro. For the assay, the 2-fold serial dilutions of arteether isomers in the 0.5-16 ug/L concentration range in three replicate wells were incubated with parasitised cell preparation at 37C in a candle jar for 30-40 h.
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:18:59 UTC 2021
Edited
by admin
on Sat Jun 26 07:18:59 UTC 2021
Record UNII
XGL7GFB9YI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEMOTIL
INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
ARTEMOTIL [WHO-DD]
Common Name English
ARTEMOTIL [WHO-IP]
Common Name English
ARTEMOTIL [MART.]
Common Name English
ARTEMOTIL [INN]
Common Name English
(3R,5AS,6R,8AS,9R,10S,12R,12AR)-10-ETHOXYDECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN
Common Name English
NSC-665971
Code English
ARTEETHER [WHO-IP]
Common Name English
.BETA.-ARTEETHER [WHO-IP]
Common Name English
ARTEETHER [MI]
Common Name English
ARTEMOTILUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
WHO-ATC P01BE04
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
Code System Code Type Description
PUBCHEM
3000469
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
MESH
C055141
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
EVMPD
SUB00596MIG
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
CAS
75887-54-6
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ARTEMOTIL
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder. Solubility: Practically insoluble in water; sparingly soluble in dichloromethane R, ethanol (~750 g/l) TS and methanol R; soluble inarachis oil R and sesame oil R. Category: Antimalarial drug. Storage: Artemotil should be kept in a well-closed container, protected from light. Labelling: The designation Artemotil for parenteral use indicates that the substance complies with the additional requirements and may be used for parenteral administration. Additional information: The parenteral form is normally intended for intramuscular administration. Requirement: Artemotil contains not less than 97.0% and not more than the equivalent of 102.0% of C17H28O5 calculated with reference to the dried substance.
DRUG BANK
DB13851
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
DRUG CENTRAL
246
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
MERCK INDEX
M2073
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY Merck Index
INN
6457
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
WIKIPEDIA
ARTEMOTIL
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
NCI_THESAURUS
C73002
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL301267
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
FDA UNII
XGL7GFB9YI
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
EPA CompTox
75887-54-6
Created by admin on Sat Jun 26 07:18:59 UTC 2021 , Edited by admin on Sat Jun 26 07:18:59 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.32.pdf