GSK369796 Dihydrochloride | N-tert-butylisoquine | CAS#1010411-21-8

MedKoo Cat#: 530320 | Name: GSK369796 Dihydrochloride

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Description:

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

GSK369796, also known as N-tert-butylisoquine, is an anti-malaria drug candidate. GSK369796 was rationally designed based on chemical, toxicological, pharmacokinetic, and pharmacodynamic considerations and was selected based on excellent activity against Plasmodium falciparum in vitro and rodent malaria parasites in vivo.

Chemical Structure

GSK369796 Dihydrochloride

CAS#1010411-21-8 (2HCl)

Theoretical Analysis

MedKoo Cat#: 530320

Name: GSK369796 Dihydrochloride

CAS#: 1010411-21-8 (2HCl)

Chemical Formula: C20H24Cl3N3O

Exact Mass: 0.0000

Molecular Weight: 428.78

Elemental Analysis: C, 56.02; H, 5.64; Cl, 24.80; N, 9.80; O, 3.73

Price and Availability

Size	Price	Availability
5mg	USD 250.00	2 Weeks
10mg	USD 450.00	2 Weeks
25mg	USD 850.00	2 Weeks
50mg	USD 1,350.00	2 Weeks
100mg	USD 2,150.00	2 Weeks

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Related CAS #

459133-38-1 (free base) 1010411-21-8 (2HCl)

Synonym

GSK369796 Dihydrochloride; GSK369796 2HCl; GSK 369796; GSK-369796; GSK369796; N-tert-Butyl isoquine; N-tert-Butylisoquine

IUPAC/Chemical Name

2-[(tert-Butylamino)methyl]-5-[(7-chloroquinolin-4-yl)amino]phenol Dihydrochloride

InChi Key

UDVALKJFXQVZSI-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H22ClN3O.2ClH/c1-20(2,3)23-12-13-4-6-15(11-19(13)25)24-17-8-9-22-18-10-14(21)5-7-16(17)18;;/h4-11,23,25H,12H2,1-3H3,(H,22,24);2*1H

SMILES Code

OC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1CNC(C)(C)C.[H]Cl.[H]Cl

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

GSK369796 Dihydrochloride is an affordable and effective antimalarial and inhibits hERG potassium ion channel repolarization with an IC50 of 7.5 μM.

In vitro activity:

It is also clear that N-tert-butyl analogue 2k (GSK369796 Dihydrochloride) is potent against chloroquine resistant strains, though it is not quite as active as amodiaquine against both chloroquine-sensitive and resistant parasites. On the basis of the activity presented in Table 4, 2k was selected alongside its direct 4-chloro analogue for further studies in the mouse model of malaria. Reference: J Med Chem. 2009 Apr 9;52(7):1828-44. https://pubmed.ncbi.nlm.nih.gov/19284751/

In vivo activity:

The therapeutic efficacy of 2k (GSK369796 Dihydrochloride), 3k, and selected 4-aminoquinolines was evaluated in a standard “4-day test” in CD1 mice infected intravenously with the murine pathogen P berghei ANKA at GSK, Tres Cantos, Spain (Table 5). Isoquine (1d) showed in vivo therapeutic efficacy against Plasmodium berghei ANKA with ED50 and ED90 in the same range as that of amodiaquine. Analogue 2k was also potent in this in vivo assay with an ED50 value of 5.3 mg/kg, whereas chloro analogue 3k was less potent with an ED50 of 13.4 mg/ kg. Reference: J Med Chem. 2009 Apr 9;52(7):1828-44. https://pubmed.ncbi.nlm.nih.gov/19284751/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	233.22
	Water	50.0	116.61

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 428.78 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.

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

Formulation protocol:

1. O'Neill PM, Shone AE, Stanford D, Nixon G, Asadollahy E, Park BK, Maggs JL, Roberts P, Stocks PA, Biagini G, Bray PG, Davies J, Berry N, Hall C, Rimmer K, Winstanley PA, Hindley S, Bambal RB, Davis CB, Bates M, Gresham SL, Brigandi RA, Gomez-de-Las-Heras FM, Gargallo DV, Parapini S, Vivas L, Lander H, Taramelli D, Ward SA. Synthesis, antimalarial activity, and preclinical pharmacology of a novel series of 4'-fluoro and 4'-chloro analogues of amodiaquine. Identification of a suitable "back-up" compound for N-tert-butyl isoquine. J Med Chem. 2009 Apr 9;52(7):1828-44. doi: 10.1021/jm8012757. PMID: 19284751.

In vitro protocol:

In vivo protocol:

1: O'Neill PM, Shone AE, Stanford D, Nixon G, Asadollahy E, Park BK, Maggs JL, Roberts P, Stocks PA, Biagini G, Bray PG, Davies J, Berry N, Hall C, Rimmer K, Winstanley PA, Hindley S, Bambal RB, Davis CB, Bates M, Gresham SL, Brigandi RA, Gomez-de-Las-Heras FM, Gargallo DV, Parapini S, Vivas L, Lander H, Taramelli D, Ward SA. Synthesis, antimalarial activity, and preclinical pharmacology of a novel series of 4'-fluoro and 4'-chloro analogues of amodiaquine. Identification of a suitable "back-up" compound for N-tert-butyl isoquine. J Med Chem. 2009 Apr 9;52(7):1828-44. doi: 10.1021/jm8012757. PubMed PMID: 19284751. 2: O'Neill PM, Park BK, Shone AE, Maggs JL, Roberts P, Stocks PA, Biagini GA, Bray PG, Gibbons P, Berry N, Winstanley PA, Mukhtar A, Bonar-Law R, Hindley S, Bambal RB, Davis CB, Bates M, Hart TK, Gresham SL, Lawrence RM, Brigandi RA, Gomez-delas-Heras FM, Gargallo DV, Ward SA. Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century. J Med Chem. 2009 Mar 12;52(5):1408-15. doi: 10.1021/jm8012618. PubMed PMID: 19222165.