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MedKoo Cat#: 326746 | Name: Endochin

Description:

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

Endochin is an experimental antimalarial. Since the 1940s endochin and analogues thereof were known to be causal prophylactic and potent erythrocytic stage agents in avian models.

Chemical Structure

Endochin
Endochin
CAS#354155-51-4

Theoretical Analysis

MedKoo Cat#: 326746

Name: Endochin

CAS#: 354155-51-4

Chemical Formula: C18H25NO2

Exact Mass: 287.1885

Molecular Weight: 287.40

Elemental Analysis: C, 75.22; H, 8.77; N, 4.87; O, 11.13

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 #
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Synonym
Endochin
IUPAC/Chemical Name
3-heptyl-7-methoxy-2-methylquinolin-4(1H)-one
InChi Key
BCZRFDKLLBFOHJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H25NO2/c1-4-5-6-7-8-9-15-13(2)19-17-12-14(21-3)10-11-16(17)18(15)20/h10-12H,4-9H2,1-3H3,(H,19,20)
SMILES Code
O=C1C(CCCCCCC)=C(C)NC2=C1C=CC(OC)=C2
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 287.40 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: Ortiz D, Forquer I, Boitz J, Soysa R, Elya C, Fulwiler A, Nilsen A, Polley T, Riscoe MK, Ullman B, Landfear SM. Targeting the Cytochrome bc1 Complex of Leishmania Parasites for Discovery of Novel Drugs. Antimicrob Agents Chemother. 2016 Jun 13. pii: AAC.00850-16. [Epub ahead of print] PubMed PMID: 27297476. 2: Lawres LA, Garg A, Kumar V, Bruzual I, Forquer IP, Renard I, Virji AZ, Boulard P, Rodriguez EX, Allen AJ, Pou S, Wegmann KW, Winter RW, Nilsen A, Mao J, Preston DA, Belperron AA, Bockenstedt LK, Hinrichs DJ, Riscoe MK, Doggett JS, Ben Mamoun C. Radical cure of experimental babesiosis in immunodeficient mice using a combination of an endochin-like quinolone and atovaquone. J Exp Med. 2016 Jun 27;213(7):1307-18. doi: 10.1084/jem.20151519. Epub 2016 Jun 6. PubMed PMID: 27270894; PubMed Central PMCID: PMC4925016. 3: Stickles AM, Smilkstein MJ, Morrisey JM, Li Y, Forquer IP, Kelly JX, Pou S, Winter RW, Nilsen A, Vaidya AB, Riscoe MK. Atovaquone and ELQ-300 combination therapy: A novel dual-site cytochrome bc1 inhibition strategy for malaria. Antimicrob Agents Chemother. 2016 Jun 6. pii: AAC.00791-16. [Epub ahead of print] PubMed PMID: 27270285. 4: Stickles AM, de Almeida MJ, Morrisey JM, Sheridan KA, Forquer IP, Nilsen A, Winter RW, Burrows JN, Fidock DA, Vaidya AB, Riscoe MK. Subtle changes in endochin-like quinolone structure alter the site of inhibition within the cytochrome bc1 complex of Plasmodium falciparum. Antimicrob Agents Chemother. 2015 Apr;59(4):1977-82. doi: 10.1128/AAC.04149-14. Epub 2015 Jan 20. PubMed PMID: 25605352; PubMed Central PMCID: PMC4356778. 5: Nilsen A, Miley GP, Forquer IP, Mather MW, Katneni K, Li Y, Pou S, Pershing AM, Stickles AM, Ryan E, Kelly JX, Doggett JS, White KL, Hinrichs DJ, Winter RW, Charman SA, Zakharov LN, Bathurst I, Burrows JN, Vaidya AB, Riscoe MK. Discovery, synthesis, and optimization of antimalarial 4(1H)-quinolone-3-diarylethers. J Med Chem. 2014 May 8;57(9):3818-34. doi: 10.1021/jm500147k. Epub 2014 Apr 18. PubMed PMID: 24720377; PubMed Central PMCID: PMC4018401. 6: Ojha PK, Roy K. Exploration of important sites of antimalarial Endochins for optimum structural modification using group-based QSAR (G-QSAR) modeling. Curr Comput Aided Drug Des. 2013 Sep;9(3):336-49. PubMed PMID: 24010932. 7: Li J, Li S, Bai C, Liu H, Gramatica P. Structural requirements of 3-carboxyl-4(1H)-quinolones as potential antimalarials from 2D and 3D QSAR analysis. J Mol Graph Model. 2013 Jul;44:266-77. doi: 10.1016/j.jmgm.2013.07.004. Epub 2013 Jul 19. PubMed PMID: 23911994. 8: Doggett JS, Nilsen A, Forquer I, Wegmann KW, Jones-Brando L, Yolken RH, Bordón C, Charman SA, Katneni K, Schultz T, Burrows JN, Hinrichs DJ, Meunier B, Carruthers VB, Riscoe MK. Endochin-like quinolones are highly efficacious against acute and latent experimental toxoplasmosis. Proc Natl Acad Sci U S A. 2012 Sep 25;109(39):15936-41. Epub 2012 Sep 10. PubMed PMID: 23019377; PubMed Central PMCID: PMC3465437. 9: Winter R, Kelly JX, Smilkstein MJ, Hinrichs D, Koop DR, Riscoe MK. Optimization of endochin-like quinolones for antimalarial activity. Exp Parasitol. 2011 Feb;127(2):545-51. doi: 10.1016/j.exppara.2010.10.016. Epub 2010 Oct 30. PubMed PMID: 21040724; PubMed Central PMCID: PMC3025093. 10: Cross RM, Monastyrskyi A, Mutka TS, Burrows JN, Kyle DE, Manetsch R. Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity. J Med Chem. 2010 Oct 14;53(19):7076-94. doi: 10.1021/jm1007903. PubMed PMID: 20828199. 11: Winter RW, Kelly JX, Smilkstein MJ, Dodean R, Hinrichs D, Riscoe MK. Antimalarial quinolones: synthesis, potency, and mechanistic studies. Exp Parasitol. 2008 Apr;118(4):487-97. Epub 2007 Nov 7. PubMed PMID: 18082162; PubMed Central PMCID: PMC2323441. 12: GINGRICH WD, DARROW EM. The effect of endochin on experimental toxoplasmosis. Am J Trop Med Hyg. 1951 Jan;31(1):12-7. PubMed PMID: 14799708.