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Safety Information

C1182

Sigma-Aldrich

ω-Conotoxin MVIIA

≥95% (HPLC)

Synonym(s):

SNX-111, Ziconotide

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About This Item

Empirical Formula (Hill Notation):
C102H172N36O32S7
CAS Number:
107452-89-1
Molecular Weight:
2639.13
MDL number:
MFCD00145036
UNSPSC Code:
12352202
PubChem Substance ID:
329774874
NACRES:
NA.32

Quality Level

200

Assay

≥95% (HPLC)

form

powder

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

human ... CACNA1B(774)
mouse ... CACNA1B(12287)
rat ... CACNA1B(257648)

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
039M4831V
039M4830V
092M4817V
024M4796V
024M4795V

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Christina I Schroeder et al.
Future medicinal chemistry, 4(10), 1243-1255 (2012-07-18)
Conopeptides from the venoms of marine snails have attracted much interest as leads in drug design. Currently, one drug, Prialt(®), is on the market as a treatment for chronic neuropathic pain. Conopeptides target a range of ion channels, receptors 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
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
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
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
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