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Merck
CN

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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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)

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

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)

Regulatory Information

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Certificates of Analysis (COA)

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

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Terry Pexton et al.
Expert opinion on investigational drugs, 20(9), 1277-1284 (2011-07-12)
Pain is a major burden for affected individuals and society, and controlling neuropathic pain is especially challenging. The number of drugs available is limited and treatments are often marginally effective and burdened by side effects. Voltage-gated calcium channels (VGCC) play
Tony L Yaksh et al.
Neuromodulation : journal of the International Neuromodulation Society, 15(6), 508-519 (2012-07-04)
Ziconotide is a peptide that blocks N-type calcium channels and is antihyperalgesic after intrathecal (IT) delivery. We here characterize the spinal kinetics of IT bolus and infused ziconotide in dog. Male beagle dogs (N= 5) were prepared with chronic IT
Christoph Maier et al.
Pain, 152(1), 235-237 (2010-11-03)
Despite some other known psychiatric adverse effects, ziconotide is recommended for intrathecal pain treatment with a good efficacy and safety. Although some hints in previous studies are apparent, a higher suicidality has not been accepted as a treatment risk of
Toshifumi Takasusuki et al.
Anesthesiology, 115(1), 153-164 (2011-05-18)
The authors investigated the role of different voltage-sensitive calcium channels expressed at presynaptic afferent terminals in substance P release and on nociceptive behavior evoked by intraplantar formalin by examining the effects of intrathecally delivered N- (ziconotide), T- (mibefradil), and L-type
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
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