All Photos(1)

C1182

Sigma-Aldrich

ω-Conotoxin MVIIA

≥95% (HPLC)

Synonym(s):
SNX-111, Ziconotide
Empirical Formula (Hill Notation):
C102H172N36O32S7
CAS Number:
Molecular Weight:
2639.13
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥95% (HPLC)

composition

Peptide content, ~70%

storage temp.

−20°C

SMILES string

CSCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CSSC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N2)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC3=O)C(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc4ccc(O)cc4)NC1=O)[C@@H](C)O

InChI

1S/C102H172N36O32S7/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/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)/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

BPKIMPVREBSLAJ-BSTPJGAOSA-N

Gene Information

Amino Acid Sequence

Cys-Lys-Gly-Lys-Gly-Ala-Lys-Cys-Ser-Arg-Leu-Met-Tyr-Asp-Cys-Cys-Thr-Gly-Ser-Cys-Arg-Ser-Gly-Lys-Cys-NH2

General description

ω-Conotoxin MVIIA functions as a selective inhibitor of N-type voltage-sensitive calcium channels (VSCCs). It has analgesic and neuroprotective effects. ω-Conotoxin MVIIA is used to treat neuropathic pain.

Application

Probe for calcium channel receptors; selective for different receptor subtypes.
ω-Conotoxin MVIIA has been used to study pharmacological blockade of injury-induced alterations in adult male Sprague-Dawley rats.

Biochem/physiol Actions

Neuronal N-type Ca2+ channel blocker in mammalian and amphibian brain; blocks release of GABA and glutamate at neuronal synapses.

Other Notes

Lyophilized from 0.1% TFA in H2O

Certificate of Analysis

Certificate of Origin

Whitney B Michiels et al.
The Clinical journal of pain, 27(4), 352-354 (2011-04-16)
We report a case of a 59-year-old female with severe TN who experienced satisfactory symptom relief from a single-shot trial of intrathecal ziconotide. Performed a 1 μg single-shot trial of Prialt. Report of satisfaction, no side effects, and complete face...
Denis Dupoiron et al.
Pain physician, 15(5), 395-403 (2012-09-22)
Ziconotide is a new analgesic agent administered intrathecally. It is challenging to use and can induce several and sometimes serious adverse events. A low initial dosage followed by slow titration may reduce serious adverse events. To determine whether a low...
William Raffaeli et al.
Pain physician, 14(1), 15-24 (2011-01-27)
Ziconotide is commonly used for intrathecal (IT) therapy of chronic pain, and has been recently indicated as a first-line IT drug. It is also extremely useful for patients intolerant or refractory to the common IT drugs (such as morphine). The...
Flavia Karine Rigo et al.
Cancer science, 104(9), 1226-1230 (2013-05-31)
The marine snail peptide ziconotide (ω-conotoxin MVIIA) is used as an analgesic in cancer patients refractory to opioids, but may induce severe adverse effects. Animal venoms represent a rich source of novel drugs, so we investigated the analgesic effects and...
Achim Schmidtko et al.
Lancet (London, England), 375(9725), 1569-1577 (2010-04-24)
Pharmacological management of severe chronic pain is difficult to achieve with currently available analgesic drugs, and remains a large unmet therapeutic need. The synthetic peptide ziconotide has been approved by the US Food and Drug Administration and the European Medicines...

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