Marine natural products. in clinical trials and on the market. By: Z. Janahmadi
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1 Marine natural products in clinical trials and on the market By: Z. Janahmadi
2 Presentation outline Marine natural products that are under clinical trials, or that have been approved as drugs: Antitumor Antiviral Analgesic Other applications
3 Antitumor Four drugs: on the market Cytarabine (Cytosar ) Trabectedin ( ET-743, Yondelis ) Eribulin mesylate (ET7389, Halaven ) Brentuximab vedotin (Adcetris ) Nine molecules: in clinical trials monomethylauristatin E monomethylauristatin F Dehydrodidemnin B (plitidepsin, aplidin ) Plinabulin (NPI-2358) Dolastatin-15 Marizomib (NPI-0052, Salinosporamide A) Bryostatin 1 E7974 Lurbinectedin
4 Antiviral drugs Vidarabine Arabinofuranosyladenine, adenine arabinoside, Ara-A Synthetic purine nucleoside Developed from Spongouridine Tethya crypta Streptomyces antibioticus Converted into adenine arabinoside triphosphate Inhibits viral DNA polymerase Inhibits DNA synthesis of herpes, vaccinia, and varicella zoster viruses
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6 1976: FDA approval Indications: Acute keratoconjunctivitis Recurrent epithelial keratitis caused by HSV1,2 Superficial keratitis caused by HSV that has not respond to topical idoxuridine King pharmaceuticals Discontinued in june of 2001 in US Lower therapeutic window of vidarabine relative to newer antiviral compounds currently on the market Ophthalmic oint 3% in Europe
7 Analgesic Neuropathic & chronic pain Especially in morphine unresponsive patients Ziconotide Tetrodotoxin
8 Ziconotide (Prialt ) ω- conotoxin: 25 amino acid peptide Isolated from the venom of the cone snail Conus magus
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10 Ziconotide (Prialt ) Synthesized in 1987 FDA approval: 2004 Intrathecal Management of severe chronic pain associated with cancer, AIDS, and neuropathies that is refractory to other treatment modalities
11 Ziconotide (Prialt ) Selective N-type voltage sensitive calcium channel blocker Reduces excitatory neurotransmitter release from the primary afferent nerve terminals
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15 Ziconotide (Prialt ) Fast titration regimen: serious adverse events Slow titration regimen: FDA approved Initial dose: not exceed 2.4μg/day (0.1μg/h) Optimum dose: should be slowly uptitrated ( no more than 2-3 times/week) Recommended max dose (by day 21): 19.2 μg/day
16 Ziconotide (Prialt ) Highly hydrophilic & large molecule 1mm/2h Lag time for onset & offset of analgesia Onset of pain relief: after 2-4 h Maximum effect: after 8-12 h Offset of pain relief: up to 48 h after discontinuation
17 Side effects: Dizziness Confusion Ataxia memory impairment Nystagmus Hallucination Vertigo Nausea vomiting Ziconotide (Prialt )
18 Ziconotide (Prialt ) Strong antinociceptive effects At leaset 10 times more potent than intratecal morphine No tolerance Elan corporation 2010: $6.1 M
19 Tetrodotoxin (TTX) Voltage dependent sodium channel blocker Isolated from fish, algae, and bacteria In phase III: treatment of neuropathic pain in cancer patients by IM & SQ administration Phase II: peripheral pain Tectin 15 μg/ml TTX, in 2 ml ampoules
20 Other applications Fish omega 3 acid ethyl esters (Lovaza, omacor ) Carreglose Pseudopterosin A methyl ester (VM301) Anabasine Squalamine lactate (MSI-1256F)
21 Other applications Metabolic disease Fish omega 3 acid ethyl esters (Lovaza, omacor ) FDA approval in 2004: to treat hypertriglyceridemia Inhibits TG synthesizing enzymes: decrease synthesis & serum levels of TG Major constituents being ethyl esters of Eicosapentaenoic acid Decosahexanoic acid Much lower mortality rates from cardiovascular diseases in certain ethnic population such as native Alaskans Correlated with high polyunsaturated fatty acids diets content
22 Eicosapentaenoic acid Decosahexanoic acid
23 Carreglose Carrageenans Family of linear sulfated polysaccharides Red edible seaweeds (Rhodophyceae) Food industry: gelling, thickening, and stabilizing properties Iota-carrageenan (Carreglose ) Marinomed Biotechnologie Antiviral nasal spray Protective physical anti-viral barrier in the nasal cavity
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25 Pseudopterosin A methyl ester (VM301) Hemi synthetic derivative of pseudopterosin A Diterpene glycoside Pseudopterogorgia elizabethae Anti-inflammatory & wound healing properties Phase II clinical trial: increased reepithelization, and increased the wound healing process
26 Anabasine Toxic alkaloid Several nemertinean species Paranemertes peregrine Amphiporus lactifloreus DMXBA (GTS-21): synthetic derivative
27 Stimulates α7 nicotinic acetylcholine receptors expressed in neurons and astrocytes in CNS and in peripheral macrophages Improved cognition and sensory deficit in several animal models Neuroprotective effect in vitro & in vivo Anti-inflammatory activity mediated by α7 macrophage receptor Phase I & II of clinical trials: Significant cognitive improvement in healthy young adults and in schizophrenic patients Comentis Inc.
28 Squalamine lactate (MSI-1256F) Aminosterol with antibiotic activity Isolated from the stomach of the shark squalus acanthias Potent angiogenesis inhibitor Clinical trials for cancer Clinical trials of phase II & III: Wet age-related macular degeneration
29 Conclusion Brief history of marine natural products that originated medicine, or are in advanced clinical trials First discovered as toxins In the last 25 years: Increase in the number of bioactive natural products Many more medicines will be derived from marine natural products in the near future
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