A quaternary ammonium-containing cationic surfactant with diverse biological activities
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Thonzonium (bromide)

Item No. 31253

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-[[(4-methoxyphenyl)methyl]-2-pyrimidinylamino]ethyl]-N,N-dimethyl-1-hexadecanaminium, monobromide
CAS Number
553-08-2
Synonyms
  • NC 1264
Molecular Formula
C32H55N4O • Br
Formula Weight
591.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
242 nm
SMILES
C[N+](C)(CCN(C1=NC=CC=N1)CC2=CC=C(OC)C=C2)CCCCCCCCCCCCCCCC.[Br-]
InChi Code
InChI=1S/C32H55N4O.BrH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-27-36(2,3)28-26-35(32-33-24-19-25-34-32)29-30-20-22-31(37-4)23-21-30;/h19-25H,5-18,26-29H2,1-4H3;1H/q+1;/p-1
InChi Key
WBWDWFZTSDZAIG-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Thonzonium is a quaternary ammonium-containing cationic surfactant with diverse biological activities.1,2,3,4 It is an inhibitor of F. tularensis acid phosphatase B (AcpB; Ki = 0.59 µM) and the vacuolar ATPase (V-ATPase) proton pump in C. albicans (EC50 = 69 µM in purified vacuolar membrane vesicles).1,2 Thonzonium (25-400 nM) inhibits osteoclastogenesis induced by RANKL in bone marrow-derived macrophages (BMDMs) and inhibits bone resorption by mature osteoclasts in a V-ATPase-independent manner when used at concentrations of 100 and 200 nM.3 It prevents bone loss induced by LPS in a calvarial osteolytic mouse model when administered at a dose of 5 mg/kg per day. Thonzonium induces mortality in the helminths C. oncophora, O. ostertagi, H. contortus, and T. circumcincta with EC50 values of 4.5, 10.8, 5.1, and 6.7 µM, respectively, but is cytotoxic to HEK293 and RAW 264.7 cells with CC50 values of 9.2 and 5.7 µM, respectively.4 Formulations containing thonzonium as a surfactant have been used in the treatment of external auditory canal infections, as well as mastoidectomy and fenestration cavity infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McRae, S., Pagliai, F.A., Mohapatra, N.P., et al. Inhibition of AcpA phosphatase activity with ascorbate attenuates Francisella tularensis intramacrophage survival. The Journal of Biological Chemisty 285(8), 5171-5177 (2010).

    2. Chan, C.-Y., Prudom, C., Raines, S.M., et al. Inhibitors of V-ATPase proton transport reveal uncoupling functions of tether linking cytosolic and membrane domains of V0 subunit a (Vph1p). The Journal of Biological Chemisty 287(13), 10236-10250 (2012).

    3. Zhu, X., Gao, J.J., Landao-Bassonga, E., et al. Thonzonium bromide inhibits RANKL-induced osteoclast formation and bone resorption in vitro and prevents LPS-induced bone loss in vivo. Biochem. Pharmacol. 104, 118-130 (2016).

    4. Liu, M., Landuyt, B., Klaassen, H., et al. Screening of a drug repurposing library with a nematode motility assay identifies promising anthelmintic hits against Cooperia oncophora and other ruminant parasites. Vet. Parasitol. 265, 15-18 (2019).