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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O8
Molecular Weight 384.4208
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTESUNATE

SMILES

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

InChI

InChIKey=FIHJKUPKCHIPAT-AHIGJZGOSA-N
InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1

HIDE SMILES / InChI
Molecular Formula C19H28O8
Molecular Weight 384.4208
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:38:51 UTC 2023
Edited
by admin
on Fri Dec 15 15:38:51 UTC 2023
Record UNII
60W3249T9M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTESUNATE
DASH   HSDB   INN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
ARTESUNATE [USP-RS]
Common Name English
4-OXO-4-(3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXYPYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE
Common Name English
ARTESUNATE [ORANGE BOOK]
Common Name English
LJPC-0118
Code English
BUTANEDIOIC ACID, MONO(DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-
Systematic Name English
ARTESUNATE [WHO-IP]
Common Name English
ZYSUNATE
Brand Name English
ARTESUNATE [USAN]
Common Name English
SAPHNATE
Common Name English
ARTESUNATE [HSDB]
Common Name English
ARTESUNATE [VANDF]
Common Name English
.ALPHA.-ARTESUNIC ACID
Common Name English
ARTESUNATE [MI]
Common Name English
ARTESUNATE [MART.]
Common Name English
ARTESUNATUM [WHO-IP LATIN]
Common Name English
Artesunate [WHO-DD]
Common Name English
NSC-712571
Code English
DIHYDROQINGHAOSU HEMISUCCINATE
Common Name English
3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE
Systematic Name English
DIHYDROARTEMISININE-12.ALPHA.-SUCCINATE
Common Name English
BUTANEDIOIC ACID, MONO((3R,5AS,6R,8AS,9R,10S,12R,12AR)-DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER
Common Name English
QINGHAOZHI
Common Name English
artesunate [INN]
Common Name English
ARTESUNIC ACID
Common Name English
PLASMOTRIN
Brand Name English
(3R,5AS,6R,8AS,9R,10S,12R,12AR)-DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-OL, HYDROGEN SUCCINATE
Systematic Name English
ARSUMAX
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 651218
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
FDA ORPHAN DRUG 221206
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
FDA ORPHAN DRUG 598517
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ATC P01BE03
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (ART/AMO)
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ATC P01BF03
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ATC P01BF02
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ATC P01BF04
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
WHO-ATC P01BF06
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
EU-Orphan Drug EU/3/15/1521
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
FDA ORPHAN DRUG 693719
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
FDA ORPHAN DRUG 125599
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
NCI_THESAURUS C277
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
Code System Code Type Description
DRUG CENTRAL
247
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
LACTMED
Artesunate
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
CAS
88495-63-0
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
ChEMBL
CHEMBL361497
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
INN
6459
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
RXCUI
18346
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY RxNorm
SMS_ID
100000086605
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID3042681
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
DRUG BANK
DB09274
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
MERCK INDEX
m2078
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY Merck Index
FDA UNII
60W3249T9M
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
CHEBI
63918
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
PUBCHEM
6917864
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
NCI_THESAURUS
C73005
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
HSDB
7458
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
NSC
712571
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
USAN
PP-05
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ARTESUNATE
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY Description: A fine, white crystalline powder. Solubility: Very slightly soluble in water; very soluble in dichloromethane R; freely soluble in ethanol (~750 g/l) TS and acetone R. Category: Antimalarial. Storage: Artesunate should be kept in a well-closed container or, if sterile, in a hermetically closed container. It should be protected from light. Labelling: The label states where applicable:? that the substance is free from bacterial endotoxins;? that the substance is sterile. Definition: Artesunate contains not less than 96.0% and not more than 102.0% of artesunate (C19H28O8) using Assay method A, and not less than 98.0% and not more than 102.0% of artesunate (C19H28O8) using Assay method B, both calculated with reference to the anhydrous substance.
MESH
C039726
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
RS_ITEM_NUM
1042850
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
EVMPD
SUB05576MIG
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
WIKIPEDIA
ARTESUNATE
Created by admin on Fri Dec 15 15:38:51 UTC 2023 , Edited by admin on Fri Dec 15 15:38:51 UTC 2023
PRIMARY
Related Record Type Details
OATP1B1
TRANSPORTER -> INHIBITOR
WEAK
IC50
Plasmodium falciparum
TARGET ORGANISM->INHIBITOR
IC50
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
Structure of SODIUM ARTESUNATE
SALT/SOLVATE -> PARENT
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
OAT-3
TRANSPORTER -> INHIBITOR
WEAK
Related Record Type Details
Structure of ARTENIMOL
METABOLITE ACTIVE -> PARENT
Structure of .ALPHA.-DIHYDROARTEMISININ
METABOLITE ACTIVE -> PRODRUG
ratio of alpha to beta DIHYDROARTEMISININ is 3.5
PLASMA
Related Record Type Details
Structure of ARTEMISININ
IMPURITY -> PARENT
In the chromatogram obtained with solution (1): the area of any peak corresponding to impurity B (artemisinin) is not greater than 0.5 times the area of the principal peak obtained with solution (4) (0.5%).
Structure of ANHYDRODIHYDROARTEMISNIN
IMPURITY -> PARENT
In the chromatogram obtained with solution (1): the area of any peak corresponding to impurity C, when multiplied by a correction factor of 0.07, is not greater than 0.2 times the area of the principal peak obtained with solution (4) (0.2%) the sum of the corrected area of any peak corresponding to impurity C and the areas of all other peaks, other than the principal peak, is not greater than twice the area of the principal peak obtained with solution (4) (2.0%).
Related Record Type Details
Structure of .ALPHA.-DIHYDROARTEMISININ
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

IN PATIENTS WITH SEVERE MALARIA

Biological Half-life PHARMACOKINETIC IN PATIENTS WITH SEVERE MALARIA

INTRAVENOUS ADMINISTRATION

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