MedKoo Cat#: 528904 | Name: Artefenomel

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Artefenomel, also known as OZ-439, a novel trioxolane, is a lead candidate for inclusion in a new antimalarial combination, specifically formulated for children. Artefenomel has been demonstrated curative in as little as one dose.

Chemical Structure

Artefenomel
CAS#1029939-86-3 (free base)

Theoretical Analysis

MedKoo Cat#: 528904

Name: Artefenomel

CAS#: 1029939-86-3 (free base)

Chemical Formula: C28H39NO5

Exact Mass: 469.2828

Molecular Weight: 469.62

Elemental Analysis: C, 71.61; H, 8.37; N, 2.98; O, 17.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
Synonym
OZ-439; OZ439; OZ 439; Artefenomel.
IUPAC/Chemical Name
4-(2-(4-(dispiro[adamantane-2,3'-[1,2,4]trioxolane-5',1''-cyclohexan]-4''-yl)phenoxy)ethyl)morpholine
InChi Key
XLCNVWUKICLURR-LVNZGLPESA-N
InChi Code
InChI=1S/C28H39NO5/c1-3-26(31-14-11-29-9-12-30-13-10-29)4-2-22(1)23-5-7-27(8-6-23)32-28(34-33-27)24-16-20-15-21(18-24)19-25(28)17-20/h1-4,20-21,23-25H,5-19H2/t20?,21?,23?,24?,25?,27-,28-
SMILES Code
N1(CCOC2=CC=C(C3CC[C@]4(OO[C@]5(C(C6)CC7CC6CC5C7)O4)CC3)C=C2)CCOCC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 469.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Phyo AP, Jittamala P, Nosten FH, Pukrittayakamee S, Imwong M, White NJ, Duparc S, Macintyre F, Baker M, Möhrle JJ. Antimalarial activity of artefenomel (OZ439), a novel synthetic antimalarial endoperoxide, in patients with Plasmodium falciparum and Plasmodium vivax malaria: an open-label phase 2 trial. Lancet Infect Dis. 2016 Jan;16(1):61-9. doi: 10.1016/S1473-3099(15)00320-5. PubMed PMID: 26448141; PubMed Central PMCID: PMC4700386. 2: McCarthy JS, Baker M, O'Rourke P, Marquart L, Griffin P, Hooft van Huijsduijnen R, Möhrle JJ. Efficacy of OZ439 (artefenomel) against early Plasmodium falciparum blood-stage malaria infection in healthy volunteers. J Antimicrob Chemother. 2016 Sep;71(9):2620-7. doi: 10.1093/jac/dkw174. PubMed PMID: 27272721; PubMed Central PMCID: PMC4992851. 3: Kim HS, Hammill JT, Guy RK. Seeking the Elusive Long-Acting Ozonide: Discovery of Artefenomel (OZ439). J Med Chem. 2017 Mar 15. doi: 10.1021/acs.jmedchem.7b00299. [Epub ahead of print] PubMed PMID: 28296396. 4: Jourdan J, Matile H, Reift E, Biehlmaier O, Dong Y, Wang X, Mäser P, Vennerstrom JL, Wittlin S. Monoclonal Antibodies That Recognize the Alkylation Signature of Antimalarial Ozonides OZ277 (Arterolane) and OZ439 (Artefenomel). ACS Infect Dis. 2016 Jan 8;2(1):54-61. PubMed PMID: 26819968; PubMed Central PMCID: PMC4718528. 5: Dong Y, Wang X, Kamaraj S, Bulbule VJ, Chiu FC, Chollet J, Dhanasekaran M, Hein CD, Papastogiannidis P, Morizzi J, Shackleford DM, Barker H, Ryan E, Scheurer C, Tang Y, Zhao Q, Zhou L, White KL, Urwyler H, Charman WN, Matile H, Wittlin S, Charman SA, Vennerstrom JL. Structure-Activity Relationship of the Antimalarial Ozonide Artefenomel (OZ439). J Med Chem. 2017 Jan 18. doi: 10.1021/acs.jmedchem.6b01586. [Epub ahead of print] PubMed PMID: 28052200. 6: Rosenthal PJ. Artefenomel: a promising new antimalarial drug. Lancet Infect Dis. 2016 Jan;16(1):6-8. doi: 10.1016/S1473-3099(15)00343-6. PubMed PMID: 26448142. 7: White NJ. Can new treatment developments combat resistance in malaria? Expert Opin Pharmacother. 2016 Jul;17(10):1303-7. doi: 10.1080/14656566.2016.1187134. PubMed PMID: 27191998. 8: Yang T, Xie SC, Cao P, Giannangelo C, McCaw J, Creek DJ, Charman SA, Klonis N, Tilley L. Comparison of the Exposure Time Dependence of the Activities of Synthetic Ozonide Antimalarials and Dihydroartemisinin against K13 Wild-Type and Mutant Plasmodium falciparum Strains. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4501-10. doi: 10.1128/AAC.00574-16. PubMed PMID: 27161632; PubMed Central PMCID: PMC4958167.