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ziconotide

Structure via PubChem · Public domain (PubChem)

EntityQ198473· pop 18· linked from 603 articles

ziconotide

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Also known as SNX-111

Ziconotide, sold under the brand name Prialt, also called intrathecal ziconotide (ITZ) because of its administration route, is an atypical analgesic agent for the amelioration of severe and chronic pain. Derived from Conus magus, a cone snail, it is the synthetic form of an ω-conotoxin peptide.

Key facts

Drug.S
7
Drug.Watchedfields
changed
Drug.Verifiedfields
changed
Drug.verifiedrevid
409117228
Drug.image
Structural formula of ziconotide.png
Drug.image_class
skin-invert-image
Drug.width
250
Drug.image2
Ziconotide 1DW5.png
Drug.image_class2
bg-transparent
Drug.width2
250
Drug.tradename
Prialt
Drug.DailyMedID
Ziconotide
Drug.routes_of_administration
Intrathecal
Drug.ATC_prefix
N02
Drug.ATC_suffix
BG08
Drug.legal_US
Rx-only
Drug.legal_EU
Rx-only
Drug.legal_status
Rx-only

via Wikipedia infobox

Chemical data

Formula
C102H172N36O32S7
Molecular weight
2639.2 g/mol
IUPAC name
2-[(1R,4S,7S,13S,16R,21R,24S,27S,30S,33S,36S,39S,42R,45S,48S,54S,60S,63R,68R,71S,77S)-63-amino-13,45,54,60-tetrakis(4-aminobutyl)-4,36-bis(3-carbamimidamidopropyl)-2,5,8,11,14,23,26,29,32,35,38,41,44,47,50,53,56,59,62,69,72,75,78,85-tetracosahydroxy-16-(C-hydroxycarbonimidoyl)-71-[(1R)-1-hydroxyethyl]-7,39,77-tris(hydroxymethyl)-27-[(4-hydroxyphenyl)methyl]-48-methyl-33-(2-methylpropyl)-30-(2-methylsulfanylethyl)-18,19,65,66,81,82-hexathia-3,6,9,12,15,22,25,28,31,34,37,40,43,46,49,52,55,58,61,70,73,76,79,84-tetracosazatricyclo[40.37.4.221,68]pentaoctaconta-2,5,8,11,14,22,25,28,31,34,37,40,43,46,49,52,55,58,61,69,72,75,78,84-tetracosaen-24-yl]acetic acid
SMILES
C[C@H]1C(=N[C@H](C(=N[C@H]2CSSC[C@H]3C(=N[C@H](C(=N[C@H](C(=NCC(=N[C@H](C(=N[C@@H](CSSC[C@@H](C(=N[C@@H](CSSC[C@@H](C(=N[C@H](C(=NCC(=N[C@H](C(=NCC(=N1)O)O)CCCCN)O)O)CCCCN)O)N)C(=N[C@H](C(=NCC(=N[C@H](C(=N3)O)CO)O)O)[C@@H](C)O)O)O)N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C2O)CO)O)CCCNC(=N)N)O)CC(C)C)O)CCSC)O)CC4=CC=C(C=C4)O)O)CC(=O)O)O)C(=N)O)O)CCCCN)O)O)CO)O)CCCNC(=N)N)O)O)CCCCN)O
InChIKey
BPKIMPVREBSLAJ-QTBYCLKRSA-N
XLogP
-5.4
Polar surface area
1400 Ų
H-bond donors
43
H-bond acceptors
71
Formal charge
0

via PubChem

Research

482 papers

via PubMed

Wikidata facts

Subclass of
chemical compound
Mass
2637.098334344
Has use
medication
Show 8 more facts
chemical formula
C₁₀₂H₁₇₂N₃₆O₃₂S₇
World Health Organisation international non-proprietary name
ziconotide
canonical SMILES
CC1C(=O)NC(C(=O)NC2CSSCC3C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(CSSCC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NCC(=O)N1)CCCCN)CCCCN)N)C(=O)NC(C(=O)NCC(=O)NC(C(=O)N3)CO)C(C)O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CO)CCCNC(=N)N)CC(C)C)CCSC)CC4=CC=C(C=C4)O)CC(=O)O)C(=O)N)CCCCN)CO)CCCNC(=N)N)CCCCN
defined daily dose
12
NCI Thesaurus ID
C1475
subject has role
calcium channel blocker
medical condition treated
complex regional pain syndrome
Commons category
Ziconotide
Sources (2)

via Wikidata · CC0

~5 min read

Encyclopedic overview

7 sections
Contents
  • Medical uses
  • Adverse effects
  • Mechanism of action
  • Structure
  • Discovery
  • References
  • External links

Ziconotide, sold under the brand name Prialt, also called intrathecal ziconotide (ITZ) because of its administration route, is an atypical analgesic agent for the amelioration of severe and chronic pain. Derived from Conus magus, a cone snail, it is the synthetic form of an ω-conotoxin peptide.

In December 2004 the US Food and Drug Administration (FDA) approved ziconotide when delivered as an infusion into the cerebrospinal fluid using an intrathecal pump system.

Excerpted from Wikipedia’s “ziconotide” article, available under the CC BY-SA 4.0 licence.

Available in 17 languages

via Wikidata sitelinks · CC0