A synthetic peptide blocker of N-type calcium channels
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Ziconotide (trifluoroacetate salt)

Item No. 23913

Technical Information
Formal Name
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-L-cysteinamide, cyclic (1→16),(8→20),(15→25)-tris(disulfide), trifluoroacetate salt
CAS Number
1660960-77-9
Synonyms
  • ω-Conotoxin MVIIA
  • SNX-111
Molecular Formula
C102H172N36O32S7 • XCF3COOH
Formula Weight
Purity
≥95%
A lyophilized powder
Water: 1 mg/ml
SMILES
NC([C@@H](N1)CSSC[C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC(C)C)NC([C@H](CCCNC(N)=N)NC([C@H](CO)NC([C@@H](NC([C@H](CCCCN)NC([C@@H](NC(CNC([C@H](CCCCN)NC(CNC([C@H](CCCCN)NC([C@@H](N[H])CSSC[C@H](N2)C(N[C@]([C@@H](C)O)([H])C(NCC(N[C@@H](CO)C3=O)=O)=O)=O)=O)=O)=O)=O)=O)C)=O)=O)CSSC[C@H](N3)C(N[C@@H](CCCNC(N)=N)C(N[C@@H](CO)C(NCC(N[C@@H](CCCCN)C1=O)=O)=O)=O)=O)=O)=O)=O)=O)CCSC)=O)CC4=CC=C(O)C=C4)=O)CC(O)=O)=O)C2=O)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C102H172N36O32S7.C2HF3O2/c1-50(2)34-63-91(161)127-62(26-33-171-5)90(160)129-64(35-53-22-24-54(143)25-23-53)92(162)130-65(36-78(148)149)93(163)135-72-48-175-173-45-69(80(108)150)133-86(156)58(18-8-12-29-105)121-76(146)39-117-85(155)66(41-139)131-88(158)61(21-15-32-114-102(111)112)126-96(166)70-46-176-177-47-71(97(167)132-68(43-141)95(165)125-60(87(157)128-63)20-14-31-113-101(109)110)134-89(159)59(19-9-13-30-106)123-81(151)51(3)119-74(144)37-115-83(153)56(16-6-10-27-103)120-75(145)38-116-84(154)57(17-7-11-28-104)124-82(152)55(107)44-172-174-49-73(137-98(72)168)99(169)138-79(52(4)142)100(170)118-40-77(147)122-67(42-140)94(164)136-70;3-2(4,5)1(6)7/h22-25,50-52,55-73,79,139-143H,6-21,26-49,103-107H2,1-5H3,(H2,108,150)(H,115,153)(H,116,154)(H,117,155)(H,118,170)(H,119,144)(H,120,145)(H,121,146)(H,122,147)(H,123,151)(H,124,152)(H,125,165)(H,126,166)(H,127,161)(H,128,157)(H,129,160)(H,130,162)(H,131,158)(H,132,167)(H,133,156)(H,134,159)(H,135,163)(H,136,164)(H,137,168)(H,138,169)(H,148,149)(H4,109,110,113)(H4,111,112,114);(H,6,7)/t51-,52+,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,79-;/m0./s1
InChi Key
WFFCQKDBWSMRCD-XZSNVYKZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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 (Kds = 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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 alNeuronal 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 alInteractions 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 Siesjö, 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).