ARTEMISONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H31NO6S
Molecular Weight	401.518
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@H]([C@@H]2C)N5CCS(=O)(=O)CC5)O4

InChI

InChIKey=FDMUNKXWYMSZIR-NQWKWHCYSA-N

InChI=1S/C19H31NO6S/c1-12-4-5-15-13(2)16(20-8-10-27(21,22)11-9-20)23-17-19(15)14(12)6-7-18(3,24-17)25-26-19/h12-17H,4-11H2,1-3H3/t12-,13-,14+,15+,16-,17-,18-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H31NO6S
Molecular Weight	401.518
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00936767 | https://www.ncbi.nlm.nih.gov/pubmed/27216383 | https://www.ncbi.nlm.nih.gov/pubmed/26282380

Artemisone (also known as BAY-44-9585; BAY-449585) is a 10-amino-artemisinin derivative that is markedly superior in vitro and in vivo to current artemisinins against malaria and also possesses antitumor activity. Nonetheless, its low water solubility and bioavailability has limited its clinical use, that is why was studied the encapsulated artemisone against human melanoma A-375. In addition, artemisone has the potential to be efficacious for the treatment of H. pylori infection, especially in combination with antibiotics.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Uncomplicated falciparum malaria 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16444785	Primary	Phase II 1132	Unknown Approved Use Unknown
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26282380	Primary	Not Provided 504	Unknown Approved Use Unknown
Helicobacter pylori infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216383	Primary	Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
95 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18559649	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARTEMISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
130.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18559649	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARTEMISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
190.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18559649	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARTEMISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
337.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18559649	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARTEMISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18559649	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARTEMISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18559649	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARTEMISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
Chem Scene	CS-0015600	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0015600
MedChem Express	HY-19502	https://www.medchemexpress.com/search.html?q=HY-19502&ft=&fa=&fp=
MolPort	MolPort-046-697-122	https://www.molport.com/shop/molecule-link/MolPort-046-697-122

PubMed

Title	Date	PubMed
Artemisone--a highly active antimalarial drug of the artemisinin class.	2006 Mar 20	16444785
Artemisinin-derived dimers have greatly improved anti-cytomegalovirus activity compared to artemisinin monomers.	2010 Apr 28	20442781
In vitro study of the anti-cancer effects of artemisone alone or in combination with other chemotherapeutic agents.	2011 Mar	20490800
In vitro activity of artemisone and artemisinin derivatives against extracellular and intracellular Helicobacter pylori.	2016 Jul	27216383

Patents

Sample Use Guides

In Vivo Use Guide

Artemisone 4 mg/kg/day for 3 days plus mefloquine 15mg/kg on day 3 and 10mg/kg on day 4

Route of Administration: Oral

In Vitro Use Guide

The in vitro activity of the new artemisinin derivative artemisone as well as other molecules of the same class against Helicobacter pylori and their effects when combined with standard antibiotics were evaluated. Artemisone showed MIC50 and MIC90 values of 0.25 mg/L and 0.5 mg/L, respectively, and an MBC50 value of 0.5 mg/L. Artemisone was synergistic with amoxicillin in 60% of strains, with clarithromycin in 40% and with metronidazole in 20%.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:26:36 UTC 2023` Edited by `admin` on `Fri Dec 15 17:26:36 UTC 2023`
Record UNII	796LMW5BUZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARTEMISONE

Official Name

English

4-((3R,5AS,6R,8AS,9R,10R,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-12H-3,12-EPOXYPYRANO(4,3-J)(1,2)BENZODIOXEPIN-10-YL)THIOMORPHOLINE-1,1-DIONE

Common Name

English

BAY 44-9585

Code

English

BAY-449585

Code

English

ARTEMIFONE

Common Name

English

artemisone [INN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

590117