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Merck

C1182

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
NACRES:
NA.32
PubChem Substance ID:
329774874
UNSPSC Code:
12352202
MDL number:
MFCD00145036

Key Documents

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Product Name

ω-Conotoxin MVIIA, ≥95% (HPLC)

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

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 key

BPKIMPVREBSLAJ-BSTPJGAOSA-N

assay

≥95% (HPLC)

form

powder

composition

Peptide content, ~70%

storage temp.

−20°C

Quality Level

200

Gene Information

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

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.

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.

Other Notes

Lyophilized from 0.1% TFA in H2O

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

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

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Pharmacotherapeutic potential of omega-conotoxin MVIIA (SNX-111), an N-type neuronal calcium channel blocker found in the venom of Conus magus.
S S Bowersox et al.
Toxicon : official journal of the International Society on Toxinology, 36(11), 1651-1658 (1998-10-29)
Nalin L Subasinghe et al.
Bioorganic & medicinal chemistry letters, 22(12), 4080-4083 (2012-05-23)
Selective blockers of the N-type calcium channel have proven to be effective in animal models of chronic pain. However, even though intrathecally delivered synthetic ω-conotoxin MVIIA from Conus magnus (ziconotide [Prialt®]) has been approved for the treatment of chronic pain
Hooman Bozorgi et al.
Behavioural brain research, 390, 112647-112647 (2020-05-20)
The lack of oral or injectable formulations of ziconotide (ω-conotoxin peptide), a novel analgesic agent, limits research on potential neurobehavioral protective properties of this substance, including antidepressant-like effects. Here we expose rats to a stress paradigm that induces depression and
Seungkyu Lee et al.
Molecular pain, 6, 97-97 (2010-12-22)
N-type Ca2+ channels (Ca(v)2.2) play an important role in the transmission of pain signals to the central nervous system. ω-Conotoxin (CTx)-MVIIA, also called ziconotide (Prialt®), effectively alleviates pain, without causing addiction, by blocking the pores of these channels. Unfortunately, CTx-MVIIA
Hypersensitive glutamate signaling correlates with the development of late-onset behavioral morbidity in diffuse brain-injured circuitry
Thomas TC, et al.
Journal of Neurotrauma, 29(2), 187-200 (2012)
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