Ziconotide Polyacetate

• CAT Number: R011808
• CAS Number: 107452-89-1
• Molecular Formula: C102H172N36O32S7
• Molecular Weight: 2639.138
• Purity: ≥95%
• Synonyms: ω-Conotoxin M VIIA Acetate; ω-Conopeptide MVIIA Acetate; Prialt Acetate; SNX 111
• Target: Neuronal Signaling
• Storage: -20°C
• 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)-16-carbamoyl-71-[(1R)-1-hydroxyethyl]-7,39,77-tris(hydroxymethyl)-27-[(4-hydroxyphenyl)methyl]-48-methyl-33-(2-methylpropyl)-30-(2-methylsulfanylethyl)-2,5,8,11,14,23,26,29,32,35,38,41,44,47,50,53,56,59,62,69,72,75,78,85-tetracosaoxo-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]pentaoctacontan-24-yl]acetic acid
• 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
• InChIKey: BPKIMPVREBSLAJ-QTBYCLKRSA-N
• 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

Ziconotide Polyacetate (CAS 107452-89-1) is a synthetic, nonopiod, twenty-five amino acid polybasic peptide analogue of an omega-conotoxin derived from the marine snail Conus magus with analgesic activity. It is a N-type Ca2+ channel blocker, inhibiting transmission from pain-sensing primary nociceptors. This agent may exhibit significant analgesic activity in refractory pain.

Omega-CgTx MVII A and Omega-CgTx GVI A (from Conus magus) are both neuronal Ca2+ channels blockers and appear to compete for the same sites in mammalian brain, but they seem to present some differences in their receptor binding characteristics, in particular the high affinity binding of Omega-CgTx MVII A has narrower specificity in amphibian brain.

Reference

1. Olivera et al., /Neuronal calcium channel antagonists. Discrimination between calcium channel subtypes using Omega-conotoxin from Conus magus venom./ Biochemistry. (1987) 26:2086-2090
2.Pope, Jason E., and Timothy R. Deer. "Ziconotide: a clinical update and pharmacologic review." Expert opinion on pharmacotherapy 14.7 (2013): 957-966.
3.Atanassoff, Peter G., et al. "Ziconotide, a new N-type calcium channel blocker, administered intrathecally for acute postoperative pain." Regional Anesthesia & Pain Medicine 25.3 (2000): 274-278.