ziconotide   Click here for help

GtoPdb Ligand ID: 2536

Synonyms: ω-conotoxin MVIIA | Prialt® | SNX-111
Approved drug
ziconotide is an approved drug (FDA (2004), EMA (2005))
Compound class: Peptide or derivative
Comment: Ziconotide is the INN for synthetically produced ω-conotoxin which was identified and extracted from the venom of Conus magus (Magus cone or Magician's cone snail).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NCCCCC1NC(=O)C(C)NC(=O)CNC(=O)C(CCCCN)NC(=O)CNC(=O)C(CCCCN)NC(=O)C(N)CSSCC2C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC3CSSCC(NC1=O)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)NC(Cc1ccc(cc1)O)C(=O)NC(CC(=O)O)C(=O)NC(C(=O)N2)CSSCC(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC3=O)CCCNC(=N)N)CO)CCCCN)C(=O)N)CO)C(O)C
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CSSC[C@H]2C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H]3CSSC[C@H](NC1=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N2)CSSC[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC3=O)CCCNC(=N)N)CO)CCCCN)C(=O)N)CO)[C@H](O)C
InChI 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-QTBYCLKRSA-N
Bioactivity Comments
Bioactivity data may have been generated using either the mollusc-derived peptide or the synthetically manufactured version.
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Cav2.2 Rn Channel blocker Antagonist 7.7 – 10.3 pIC50 - 2,5
⤷ pIC50 7.7 – 10.3 [2,5]
Voltage: Physiological
Cav2.1 Rn Channel blocker Antagonist 6.3 pIC50 - 5
⤷ pIC50 6.3 [5]
Voltage: Physiological
Cav2.2 Hs Channel blocker Antagonist 1.0 pIC50 - 3
⤷ pIC50 1.0 [3]
Voltage: -90.0 mV
Targets where the ligand is described in the comment field
Target Comment
Cav2.1 All three Cav2.x types directly contribute towards triggering neurotransmitter release at fast synapses in the mammalian nervous system. In many cell types, P- and Q-current components cannot be adequately separated and many researchers in the field have therefore adopted the terminology 'P/Q-type' current when referring to either component. Both of these physiologically defined current types are conducted by alternative forms of Cav2.1. Ziconotide (a synthetic peptide equivalent to ziconotide) has been approved for the treatment of chronic pain [7].