L-Cysteinamide, L-cysteinyl-L-lysylglycyl-L-lysylglycyl-L-alanyl-L-lysyl-L-cysteinyl-L-seryl-L-arginyl-L-leucyl-L-methionyl-L-tyrosyl-L-α-aspartyl-L-cysteinyl-L-cysteinyl-L-threonylglycyl-L-seryl-L-cysteinyl-L-arginyl-L-serylglycyl-L-lysyl-, cyclic (1→16),(8→20),(15→25)-tris(disulfide), 2,2,2-trifluoroacetate (1:?)

Product NameL-Cysteinamide, L-cysteinyl-L-lysylglycyl-L-lysylglycyl-L-alanyl-L-lysyl-L-cysteinyl-L-seryl-L-arginyl-L-leucyl-L-methionyl-L-tyrosyl-L-α-aspartyl-L-cysteinyl-L-cysteinyl-L-threonylglycyl-L-seryl-L-cysteinyl-L-arginyl-L-serylglycyl-L-lysyl-, cyclic (1→16),(8→20),(15→25)-tris(disulfide), 2,2,2-trifluoroacetate (1:?)
CAS1660960-77-9
MFC104H173F3N36O34S7
MW2753.16
EINECS
MOL File1660960-77-9.mol

Chemical Properties

solubility	Water: 1 mg/ml
form	A lyophilized powder

Usage And Synthesis

Description

Ziconotide is a synthetic version of ω-conopeptide MVIIA, a peptide toxin originally found in the venom of the fish-eating marine snail C. magus, that blocks N-type calcium channels in rat brain membranes (K_ds = 1.1-18 pM; IC₅₀s = 2-55 pM).¹,² It blocks high-voltage-activated calcium currents in rat superior cervical ganglion neurons (IC₅₀ = 32 nM) as well as depolarization-induced norepinephrine release by rat peripheral sympathetic efferent neurons and in rat hippocampus (IC₅₀s = 1.2 and 5.5 nM, respectively).¹ Intrathecal administration of ziconotide inhibits formalin-induced flinch responses and increases the paw withdrawal threshold in the paw pressure test in rats (ED₅₀s = 0.11 and 0.60 μg, respectively), indicating antinociceptive effects.³ It decreases latency to tail withdrawal in a hot plate test in a rat model of sciatic chronic constriction injury.¹ Ziconotide also reduces infarct volume post ischemia in a rat model of transient focal ischemia.⁴

References

1. McGivern, J.G. Ziconotide: A review of its pharmacology and use in the treatment of pain Neurophyschiatr. Dis. Treat. 3(1),69-85(2007).
2. Olivera, B.M., Cruz, L.J., de Santos, V., et al. Neuronal calcium channel antagonists. Discrimination between calcium channel subtypes using ω-conotoxin from Conus magus venom Biochemistry 26(8),2086-2090(1987).
3. Wang, Y.X., Gao, D., Pettus, M., et al. Interactions of intrathecally administered ziconotide, a selective blocker of neuronal N-type voltage-sensitive calcium channels, with morphine on nociception in rats Pain 84(2-3),271-281(2000).
4. Zhao, Q., Smith, M.L., and Siesj, B.K. The omega-conopeptide SNX-111, an N-type calcium channel blocker, dramatically ameliorates brain damage due to transient focal ischaemia Acta. Physiol. Scand. 150(4),459-461(1994).

L-Cysteinamide, L-cysteinyl-L-lysylglycyl-L-lysylglycyl-L-alanyl-L-lysyl-L-cysteinyl-L-seryl-L-arginyl-L-leucyl-L-methionyl-L-tyrosyl-L-α-aspartyl-L-cysteinyl-L-cysteinyl-L-threonylglycyl-L-seryl-L-cysteinyl-L-arginyl-L-serylglycyl-L-lysyl-, cyclic (1→16),(8→20),(15→25)-tris(disulfide), 2,2,2-trifluoroacetate (1:?) Supplier

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