Artesunate sodiumProduct ingredient for Artesunate

Name

Artesunate sodium

Drug Entry

Artesunate

Artesunate is indicated for the initial treatment of severe malaria.⁸ The World Health Organization recommends artesunate as first line treatment for severe malaria.⁶ Artesunate was developed out of a need for a more hydrophilic derivative of artemisinin.⁵

Artesunate was granted FDA approval on 26 May 2020.⁸

See full entry for Artesunate

Accession Number

DBSALT001279

Structure

Similar Structures

Synonyms

Artesunate sodium / Dihydroartemisinin alpha-hemisuccinate sodium salt / Sodium artesunate / Sodium dihydroarteannuin hydrogen succinate monoester

External IDs

SM 804 / SM-804

UNII

CN5E49Z611

CAS Number

82864-68-4

Weight

Average: 406.407
Monoisotopic: 406.16036211

Chemical Formula

C₁₉H₂₇NaO₈

InChI Key

ZISJLHQNEVGTIU-RFEYTNPVSA-M

InChI

InChI=1S/C19H28O8.Na/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);/q;+1/p-1/t10-,11-,12+,13+,16-,17-,18-,19-;/m1./s1

IUPAC Name

sodium 4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoate

SMILES

[Na+].[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

External Links

ChemSpider: 23269779
ChEMBL: CHEMBL207675

Predicted Properties

Property	Value	Source
Water Solubility	0.795 mg/mL	ALOGPS
logP	2.7	ALOGPS
logP	3.1	Chemaxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.77	Chemaxon
pKa (Strongest Basic)	-4.2	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	7	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	103.35 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	100.79 m³·mol^-1	Chemaxon
Polarizability	39.06 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Artesunate sodiumProduct ingredient for Artesunate

Structure for Artesunate sodium (DBSALT001279)