1. 107452-89-1
2. Conotoxin Mviia
3. Omega-conotoxinmviia
4. Schembl676878
5. Akos015896032
6. Ncgc00181313-01
7. Ft-0675902
8. Q198473
| Molecular Weight | 2639.2 g/mol |
|---|---|
| Molecular Formula | C102H172N36O32S7 |
| XLogP3 | -14 |
| Hydrogen Bond Donor Count | 42 |
| Hydrogen Bond Acceptor Count | 46 |
| Rotatable Bond Count | 40 |
| Exact Mass | 2638.1016905 g/mol |
| Monoisotopic Mass | 2637.0983357 g/mol |
| Topological Polar Surface Area | 1310 Ų |
| Heavy Atom Count | 177 |
| Formal Charge | 0 |
| Complexity | 5480 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 22 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 2 | |
|---|---|
| Drug Name | Prialt |
| PubMed Health | Ziconotide (Into the fluid around your spinal cord and brain) |
| Drug Classes | Analgesic |
| Drug Label | PRIALT contains ziconotide, a synthetic equivalent of a naturally occurring conopeptide found in the piscivorous marine snail, Conus magus. Ziconotide is a 25amino acid, polybasic peptide containing three disulfide bridges with a molecular weight o... |
| Active Ingredient | Ziconotide acetate |
| Dosage Form | Injectable |
| Route | Intrathecal |
| Strength | 500mcg/5ml (100mcg/ml); 500mcg/20ml (25mcg/ml); 100mcg/1ml (100mcg/ml) |
| Market Status | Prescription |
| Company | Jazz Pharms Intl |
| 2 of 2 | |
|---|---|
| Drug Name | Prialt |
| PubMed Health | Ziconotide (Into the fluid around your spinal cord and brain) |
| Drug Classes | Analgesic |
| Drug Label | PRIALT contains ziconotide, a synthetic equivalent of a naturally occurring conopeptide found in the piscivorous marine snail, Conus magus. Ziconotide is a 25amino acid, polybasic peptide containing three disulfide bridges with a molecular weight o... |
| Active Ingredient | Ziconotide acetate |
| Dosage Form | Injectable |
| Route | Intrathecal |
| Strength | 500mcg/5ml (100mcg/ml); 500mcg/20ml (25mcg/ml); 100mcg/1ml (100mcg/ml) |
| Market Status | Prescription |
| Company | Jazz Pharms Intl |
Ziconotide is used intrathecally for the management of severe chronic pain in patients who are intolerant of or do not obtain adequate pain relief from other therapies (e.g., systemic analgesics, adjunctive therapies, intrathecal morphine therapy) when intrathecal therapy is warranted.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2241
/BOXED WARNING/ WARNING: NEUROPSYCHIATRIC ADVERSE REACTIONS. Prialt is contraindicated in patients with a preexisting history of psychosis. Severe psychiatric symptoms and neurological impairment may occur during treatment with Prialt. Monitor all patients frequently for evidence of cognitive impairment, hallucinations, or changes in mood or consciousness. Discontinue Prialt therapy in the event of serious neurological or psychiatric signs or symptoms.
US Natl Inst Health (NIH); DailyMed. Current Medication Information. Prialt (Ziconotide) Injection, Solution. (Updated February 2013). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5449ca98-efb8-4c3b-8756-747b2349a472
Meningitis has occurred in patients receiving ziconotide, principally in individuals receiving therapy via an external microinfusion device and catheter. Meningitis may occur secondary to inadvertent contamination of the microinfusion device or as a result of CSF seeding caused by hematogenous or direct spread from an infected pump pocket or catheter tract. Patients should be monitored for signs and symptoms of meningitis (e.g., fever, headache, stiff neck, altered mental status, nausea or vomiting, seizures). Preparation of ziconotide solution and filling of the drug reservoir should be performed under aseptic conditions by trained and qualified personnel. If meningitis is suspected (especially in immunocompromised patients) or is confirmed, appropriate measures (CSF culture, anti-infective therapy, removal of the microinfusion device and catheter) should be initiated.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2241
Use of Prialt has been associated with CNS-related adverse events, including psychiatric symptoms, cognitive impairment, and decreased alertness/unresponsiveness. For the 1254 patients treated /in clinical trials/, the following cognitive adverse event rates were reported: confusion (33%), memory impairment (22%), speech disorder (14%), aphasia (12%), thinking abnormal (8%), and amnesia (1%). Cognitive impairment may appear gradually after several weeks of treatment. The PRIALT dose should be reduced or discontinued if signs or symptoms of cognitive impairment develop, but other contributing causes should also be considered. The various cognitive effects of Prialt are generally reversible within 2 weeks after drug discontinuation. The medians for time to reversal of the individual cognitive effects ranged from 3 to 15 days. The elderly (> or = 65 years of age) are at higher risk for confusion.
US Natl Inst Health (NIH); DailyMed. Current Medication Information. Prialt (Ziconotide) Injection, Solution. Feb, 2008. Available from, as of May 27, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=6893
Cognitive impairment (e.g., confusion, memory impairment, speech disorder, aphasia, abnormal thinking, amnesia) has been reported in patients receiving ziconotide. Cognitive impairment may appear gradually over several weeks and generally is reversible following discontinuance of the drug. If cognitive impairment develops, the dose of ziconotide should be reduced or the drug discontinued; other causes that could contribute to cognitive impairment should be considered.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2241
For more Drug Warnings (Complete) data for ZICONOTIDE (17 total), please visit the HSDB record page.
Ziconotide reached a maximal brain concentration of between 0.003 and 0.006% of the injected material per gram of tissue at 3-20 min after i.v. injection, and this decayed to below 0.001%/g after 2 hr. ... The peptide was perfused through in vivo dialysis probes implanted into the hippocampus. Image analysis and serial sectioning showed that diffusion of Ziconotide in the extracellular fluid around the dialysis probe was minimal, with the peptide located within 1 mm of the probe after 2 hr. ... Passage from blood to brain was also verified by in situ perfusion through the carotid artery. A statistically greater amount of radioactivity was found to cross the BBB after perfusion of radioiodinated Ziconotide compared to (14)C inulin.
PMID:10822104 Newcomb R et al; Peptides 21 (4): 491-501(2000)
The pharmacokinetics and pharmacodynamics of ziconotide were assessed over a 48-hour period following intrathecal (i.t.) administration (1, 5, 7.5, or 10 ug) to 22 patients with chronic, nonmalignant pain. Plasma and cerebrospinal fluid samples were obtained over a 24-hour period. Analgesic efficacy was monitored using Visual Analog Scale of Pain Intensity (VASPI) and Category Pain Relief Scores (CPRS) measurements. Pharmacokinetic (PK) parameters were calculated by noncompartmental methods. Plasma ziconotide data were insufficient for pharmacokinetic calculations. In cerebrospinal fluid, the median half-life of ziconotide was 4.5 hours. The median cerebrospinal fluid clearance and volume of distribution were 0.26 mL/min and 99 mL, respectively. Cerebrospinal fluid pharmacokinetics of ziconotide were linear, based on cumulative exposure and peak cerebrospinal fluid concentrations. A dose-related analgesia was observed. ...
PMID:12817525 Wermeling D et al; J Clin Pharmacol 43 (6): 624-36 (2003)
Intrathecal administration of ziconotide results in little systemic exposure. Following passage from the CSF into the systemic circulation, ziconotide is expected to be degraded to peptide fragments and their constituent amino acids by endopeptidases and exopeptidases present in most organs.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2242
Ziconotide is about 50% bound to human plasma proteins. The mean cerebrospinal fluid (CSF) volume of distribution (Vd) of ziconotide following intrathecal administration approximates the estimated total CSF volume (140 mL).
US Natl Inst Health (NIH); DailyMed. Current Medication Information. Prialt (Ziconotide) Injection, Solution. Feb, 2008. Available from, as of May 27, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=6893
For more Absorption, Distribution and Excretion (Complete) data for ZICONOTIDE (6 total), please visit the HSDB record page.
Ziconotide is rapidly distributed and/or metabolized in spinal cerebrospinal fluid (CSF) after intrathecal administration, followed by relatively rapid mass transport of the product from the CSF into the plasma. The relative contributions of mass transport, within and outside the spinal cord, and metabolism within it, are unclear. There is certainly evidence for rapid transport into the blood and metabolism within the spinal cord is likely to have a significant role. Following entry into the blood, the compound is quickly metabolized by normal proteolytic mechanisms, eventually to its constituent amino acids; it can be assumed that these will be further metabolized or incorporated into proteins by normal processes.
European Medicines Agency (EMEA); European Public Assessment Report (EPARs) for Authorized Medicinal Products for Human Use; Scientific Discussion; p.6 (February 28, 2008). Available from, as of May 28, 2008: https://www.emea.europa.eu/humandocs/PDFs/EPAR/Prialt/14122704en6.pdf
Ziconotide is cleaved by endopeptidases and exopeptidases at multiple sites on the peptide. Following passage from the cerebrospinal fluid (CSF) into the systemic circulation during continuous IT administration, ziconotide is expected to be susceptible to proteolytic cleavage by various ubiquitous peptidases/proteases present in most organs (e.g., kidney, liver, lung, muscle, etc.), and thus readily degraded to peptide fragments and their individual constituent free amino acids. Human and animal CSF and blood exhibit minimal hydrolytic activity toward ziconotide in vitro. The biological activity of the various expected proteolytic degradation products of ziconotide has not been assessed.
US Natl Inst Health (NIH); DailyMed. Current Medication Information. Prialt (Ziconotide) Injection, Solution. Feb, 2008. Available from, as of May 27, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=6893
The terminal half-life of ziconotide in cerebrospinal fluid after an intrathecal administration was around 4.6 hours (range 2.9-6.5 hours).
US Natl Inst Health (NIH); DailyMed. Current Medication Information. Prialt (Ziconotide) Injection, Solution. Feb, 2008. Available from, as of May 27, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=6893
/Ziconotide/ is a N-type calcium channel blocker (NCCB). Voltage-sensitive calcium channel (VSCC) conduction plays a major role in the transmission of pain. The N-type VSCC's are found in high concentrations in the dorsal root ganglion cells responsible for the spinal processing of pain. Ziconotide selectively and reversibly binds to and blocks these channels without interacting with other ion channels or cholinergic, monoaminergic or mu and delta-opioid receptors. Ziconotide thus inhibits the spinal signalling of pain.
European Medicines Agency (EMEA); European Public Assessment Report (EPARs) for Authorized Medicinal Products for Human Use; Scientific Discussion; p.1 (February 28, 2008). Available from, as of May 28, 2008: https://www.emea.europa.eu/humandocs/PDFs/EPAR/Prialt/14122704en6.pdf
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