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Merck
CN

SML1542

Sitamaquine tosylate

≥98% (HPLC)

Synonym(s):

6-Methoxy-8-(6-diethylaminohexylamine)-4-methylquinoline tosylate, N-[6-(Diethylamino)hexyl]-6-methoxy-4-methylquinolin-8-amine tosylate, N1,N1-Diethyl-N6-(6-methoxy-4-methyl-8-quinolinyl)-1,6-hexanediamine tosylate, NSC 2452, WR-6026

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About This Item

Empirical Formula (Hill Notation):
C21H33N3O · C7H8O3S
CAS Number:
1019640-33-5
Molecular Weight:
515.71
NACRES:
NA.77
PubChem Substance ID:
329825952
UNSPSC Code:
12352200
MDL number:
MFCD17392572

Key Documents

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Product Name

Sitamaquine tosylate, ≥98% (HPLC)

InChI

1S/C21H33N3O.C7H8O3S/c1-5-24(6-2)14-10-8-7-9-12-22-20-16-18(25-4)15-19-17(3)11-13-23-21(19)20;1-6-2-4-7(5-3-6)11(8,9)10/h11,13,15-16,22H,5-10,12,14H2,1-4H3;2-5H,1H3,(H,8,9,10)

SMILES string

CC1=C(C=C(OC)C=C2NCCCCCCN(CC)CC)C2=NC=C1.CC3=CC=C(S(=O)(O)=O)C=C3

InChI key

LOBPWLFCZDGYKW-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 15 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

Sitamaquine is also known as WR-6026. It is used in the treatment of visceral leishmaniasis.
Sitamaquine is an orally active 8-aminoquinoline analog that exhibit antiplasmodial and antileishmanial activities.
Sitamaquine is an orally active 8-aminoquinoline analog that exhibit antiplasmodial and antileishmanial activities. Sitamaquine accumulates in Leishmania parasites. Sitamaquine potently inhibits respiratory chain complex II (succinate dehydrogenase), which leads to an apoptosis-like death of Leishmania parasites.

Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000413874
0000413875
0000413875
0000413874
0000200173

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Sitamaquine (GlaxoSmithKline/Walter Reed Army Institute)
Yeates C
Current Opinion in Investigational Drugs, 3(10), 1446-1452 (2002)
Diana Duarte et al.
Biomolecules, 10(12) (2020-12-05)
Chemotherapy plays a key role in breast cancer therapy, but drug resistance and unwanted side effects make the treatment less effective. We propose a new combination model that combines antineoplastic drugs and antimalarials for breast cancer therapy. Cytotoxic effects of

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