A Case Study in Ion Channel Drug Discovery

A Case Study in Ion Channel Drug Discovery
David Triggle
Department of Biochemical Pharmacology, School Of Pharmacy And Pharmaceutical Sciences, SUNY, Buffalo
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Chapter Description:
Some of the of ion channel medicinal chemistry and pharmacology are well illustrated in the consideration of the group of drugs often referred to as "calcium channel antagonists" and that is a major group of therapeutically available cardiovascular drugs (hypertension, angina, peripheral vascular disorders and selected arrhythmias).
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Some of the of ion channel medicinal chemistry and pharmacology are w...
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The classification of voltage-gated calcium channels in terms of stru...
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The L-type class of voltage-sensitive calcium channel is sensitive to...
Image	4
These state-dependent interactions have a number of important therape...
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A variety of second- and third-generation 1,4-dihydropyridines have e...
Image	6
They exhibit increasing affinity for the vasculature relative to card...
Image	7
The enhanced vascular selectivity for the second-generation nisoldipi...
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The 1,4-dihydropyridine nucleus is remarkably flexible in conferring ...
Image	9
For three series of 1,4-dihydropyridines differing only in their subs...
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The correlation between the extent of voltage-dependent binding and v...
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Accordingly, differences in properties DO exist between the first-, s...
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So can drugs be developed for these calcium channel types that might ...
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What do we learn from the story of the L-type calcium channel blocker...
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Can we discover drugs for the non-L channels that will be as successf...
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Targets that have bee explored for possible uses of drugs active at N...
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Diminishing returns in drug discovery
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Mibefradil (Posicor) was a novel calcium channel blocker introduced b...
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Structure of Mibefradil.
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General properties of Mibefradil.
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Although the drug was withdrawn it have (apart from its drug interact...
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We need a good, potent and selective T-channel blocker!!!!
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The general structure of the conotoxins – disulphide–bridged pept...
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These toxins which interact with the N-type channel are effective in ...
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Drugs that interact at N-type channels may have multiple (and potenti...
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Molecules that interact with calcium channels by new routes. Gabapen...
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Thirty years of failure!!!
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Is it possible that for some diseases we need drugs that have multipl...
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Targets of potential interest for the development of new calcium chan...
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And ........it helps to have a champion -someone who really believes...
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Brief Description
The group of drugs known as the “calcium channel blockers” or “calcium channel antagonists” provide an interesting case study from two perspectives: 1. As a mature group of therapeutics agents why are they cardiovascular selective? 2. Given that there are several classes of voltage-gated calcium channels why has it been so difficult to find blockers active at the non-L-type channels?
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Jun 02, 2009	1886	VA:06:02:676:2009
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							<strong>Chapter Description:</strong>
							<div id="imagedesc" style="overflow-x: hidden; overflow-y: scroll; height: 115px; width: 100%;">Some of the of ion channel medicinal chemistry and pharmacology are well illustrated in the consideration of the group of drugs often referred to as "calcium channel antagonists" and that is a major group of therapeutically available cardiovascular drugs (hypertension, angina, peripheral vascular disorders and selected arrhythmias). </div>
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			<span style="display:none;" id="span_1">Some of the of ion channel medicinal chemistry and pharmacology are well illustrated in the consideration of the group of drugs often referred to as \'calcium channel antagonists\' and that is a major group of therapeutically available cardiovascular drugs (hypertension, angina, peripheral vascular disorders and selected arrhythmias). |~|/files/powerpoints_images/node28564/Slide1.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>1</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28568">Some of the of ion channel medicinal chemistry and pharmacology are w...</div></td>
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			<span style="display:none;" id="span_2">The classification of voltage-gated calcium channels in terms of structure, function and pharmacology.|~|/files/powerpoints_images/node28564/Slide2.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>2</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28570">The classification of voltage-gated calcium channels in terms of stru...</div></td>
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			<span style="display:none;" id="span_3">The L-type class of voltage-sensitive calcium channel is sensitive to a number of  classes of structurally distinct antagonists that interact at discrete receptor sites to block via allosteric processes channel function.|~|/files/powerpoints_images/node28564/Slide3.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>3</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28572">The L-type class of voltage-sensitive calcium channel is sensitive to...</div></td>
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			<span style="display:none;" id="span_4">These state-dependent interactions have a number of important therapeutic consequences.  The 1,4-dihydropyridines include a number of calcium channel blockers with cardiovascular activity.  The SAR of this group is illustrated here.|~|/files/powerpoints_images/node28564/Slide4.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>4</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28574">These state-dependent interactions have a number of important therape...</div></td>
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			<span style="display:none;" id="span_5">A variety of second- and third-generation 1,4-dihydropyridines have entered the market following nifedipine.  They all interact with the same voltage-gated calcium channel but have different pharmacological properties.|~|/files/powerpoints_images/node28564/Slide5.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>5</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28576">A variety of second- and third-generation 1,4-dihydropyridines have e...</div></td>
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			<span style="display:none;" id="span_6">They exhibit increasing affinity for the vasculature relative to cardiac muscle - \'vascular selectivity\'.|~|/files/powerpoints_images/node28564/Slide6.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>6</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28578">They exhibit increasing affinity for the vasculature relative to card...</div></td>
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			<span style="display:none;" id="span_7">The enhanced vascular selectivity for the second-generation nisoldipine (Sular) relative to nifedipine (Adalat) is clearly seen.  To the extent that reduced cardiac depression is a useful property this suggests that vascular selective 1,4-dihydropyridines may be therapeutically more beneficial than non-selective agents.|~|/files/powerpoints_images/node28564/Slide7.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>7</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28580">The enhanced vascular selectivity for the second-generation nisoldipi...</div></td>
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			<span style="display:none;" id="span_8">The 1,4-dihydropyridine nucleus is remarkably flexible in conferring pharmacological properties.  In this homologous series of agents there is a transition from \'vascular-selective\' to \'cardiac-selective\' agents.|~|/files/powerpoints_images/node28564/Slide8.JPG|~|563|~|422|~|0</span>
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														<td width="6%"><strong>8</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28582">The 1,4-dihydropyridine nucleus is remarkably flexible in conferring ...</div></td>
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			<span style="display:none;" id="span_9">For three series of 1,4-dihydropyridines differing only in their substitution pattern at C3 and C% of the 1,4-DHP ring there is a very large variation in their degree of voltage-dependent binding tothe L-type channel.  |~|/files/powerpoints_images/node28564/Slide9.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>9</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28584">For three series of 1,4-dihydropyridines differing only in their subs...</div></td>
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		<div id="div_10" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(10);">
			<span style="display:none;" id="span_10">The correlation between the extent of voltage-dependent binding and vascular selectivity suggest that this state-dependent binding property is a critical determinant of vascular selectivity.|~|/files/powerpoints_images/node28564/Slide10.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>10</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28586">The correlation between the extent of voltage-dependent binding and v...</div></td>
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		<div id="div_11" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(11);">
			<span style="display:none;" id="span_11">Accordingly, differences in properties DO exist between the first-, second-, and third-generation 1,4-dihydropyridines - probably with several origins.|~|/files/powerpoints_images/node28564/Slide11.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>11</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28588">Accordingly, differences in properties DO exist between the first-, s...</div></td>
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		<div id="div_12" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(12);">
			<span style="display:none;" id="span_12">So can drugs be developed for these calcium channel types that might be as clinically successful as the existing calcium channel blockers?|~|/files/powerpoints_images/node28564/Slide12.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>12</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28590">So can drugs be developed for these calcium channel types that might ...</div></td>
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		<div id="div_13" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(13);">
			<span style="display:none;" id="span_13">What do we learn from the story of the L-type calcium channel blockers?|~|/files/powerpoints_images/node28564/Slide13.JPG|~|563|~|422|~|0</span>
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								<img height="79" width="105" border="0" src="/files/powerpoints_images/node28564/Slide13.JPG" id="image_13"/>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>13</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28592">What do we learn from the story of the L-type calcium channel blocker...</div></td>
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		<div id="div_14" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(14);">
			<span style="display:none;" id="span_14">Can we discover drugs for the non-L channels that will be as successful as the L channel drugs?|~|/files/powerpoints_images/node28564/Slide14.JPG|~|563|~|422|~|0</span>
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								<img height="79" width="105" border="0" src="/files/powerpoints_images/node28564/Slide14.JPG" id="image_14"/>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>14</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28594">Can we discover drugs for the non-L channels that will be as successf...</div></td>
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		<div id="div_15" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(15);">
			<span style="display:none;" id="span_15">Targets that have bee explored for possible uses of drugs active at NON-L-type calcium channel drugs.|~|/files/powerpoints_images/node28564/Slide15.JPG|~|563|~|422|~|0</span>
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								<img height="79" width="105" border="0" src="/files/powerpoints_images/node28564/Slide15.JPG" id="image_15"/>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>15</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28596">Targets that have bee explored for possible uses of drugs active at N...</div></td>
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		<div id="div_16" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(16);">
			<span style="display:none;" id="span_16">Diminishing returns in drug discovery|~|/files/powerpoints_images/node28564/Slide16.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>16</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28598">Diminishing returns in drug discovery</div></td>
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		<div id="div_17" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(17);">
			<span style="display:none;" id="span_17">Mibefradil (Posicor) was a novel calcium channel blocker introduced by Roche (Basel), but withdrawn because of metabolic drug interactions.  No backup candidate was apparently available.  Mibefradil DOES interact with T-type channels, but also with other channel types including the L-type channel.  Because of this it is not possible to say with certainty what the cardiovascular profile of a selective T-type blocker would be.  |~|/files/powerpoints_images/node28564/Slide17.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>17</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28600">Mibefradil (Posicor) was a novel calcium channel blocker introduced b...</div></td>
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			<span style="display:none;" id="span_18">Structure of Mibefradil.|~|/files/powerpoints_images/node28564/Slide18.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>18</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28602">Structure of Mibefradil.</div></td>
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			<span style="display:none;" id="span_19">General properties of Mibefradil.|~|/files/powerpoints_images/node28564/Slide19.JPG|~|563|~|422|~|0</span>
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								<img height="79" width="105" border="0" src="/files/powerpoints_images/node28564/Slide19.JPG" id="image_19"/>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>19</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28604">General properties of Mibefradil.</div></td>
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			<span style="display:none;" id="span_20">Although the drug was withdrawn it have (apart from its drug interactions) a good CV profile and was well tolerated by patients.|~|/files/powerpoints_images/node28564/Slide20.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>20</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28606">Although the drug was withdrawn it have (apart from its drug interact...</div></td>
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		<div id="div_21" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(21);">
			<span style="display:none;" id="span_21">We need a good, potent and selective T-channel blocker!!!!|~|/files/powerpoints_images/node28564/Slide21.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>21</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28608">We need a good, potent and selective T-channel blocker!!!!</div></td>
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		<div id="div_22" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(22);">
			<span style="display:none;" id="span_22">The general structure of the conotoxins – disulphide–bridged peptides from 30-64 residues (secreted by molluscs of the Conus genus) and exhibiting a wide range of potencies against ion channels and neuronal receptors.|~|/files/powerpoints_images/node28564/Slide22.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>22</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28610">The general structure of the conotoxins – disulphide–bridged pept...</div></td>
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		<div id="div_23" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(23);">
			<span style="display:none;" id="span_23">These toxins which interact with the N-type channel are effective in chronic pain, BUT pain pathways and mechanisms are multiple in both nature and origin.|~|/files/powerpoints_images/node28564/Slide23.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>23</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28612">These toxins which interact with the N-type channel are effective in ...</div></td>
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		<div id="div_24" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(24);">
			<span style="display:none;" id="span_24">Drugs that interact at N-type channels may have multiple (and potentially undesirable) effects.|~|/files/powerpoints_images/node28564/Slide24.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>24</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28614">Drugs that interact at N-type channels may have multiple (and potenti...</div></td>
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		<div id="div_25" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(25);">
			<span style="display:none;" id="span_25">Molecules that interact with calcium channels by new routes.  Gabapentin is believed to interact at the alpha2delat subunit,  praziquantel and Way 141520 at the alpha1-beta interface.  For further discussion see: D. J. Triggle, Drug targets in the voltage-gated calcium channel family: why some are and some are not. ASSAY and Drug Development Technologies: 1: 719-733, 2003.|~|/files/powerpoints_images/node28564/Slide25.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>25</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28616">Molecules that interact with calcium channels by new routes.  Gabapen...</div></td>
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		<div id="div_26" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(26);">
			<span style="display:none;" id="span_26">|~|/files/powerpoints_images/node28564/Slide26.JPG|~|563|~|422|~|0</span>
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								<img height="79" width="105" border="0" src="/files/powerpoints_images/node28564/Slide26.JPG" id="image_26"/>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>26</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28618"></div></td>
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		<div id="div_27" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(27);">
			<span style="display:none;" id="span_27">Thirty years of failure!!!|~|/files/powerpoints_images/node28564/Slide27.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>27</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28620">Thirty years of failure!!!</div></td>
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		<div id="div_28" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(28);">
			<span style="display:none;" id="span_28">|~|/files/powerpoints_images/node28564/Slide28.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>28</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28622"></div></td>
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			<span style="display:none;" id="span_29">Is it possible that for some diseases we need drugs that have multiple sites of action?  If so what challenges does this offer to drug design?|~|/files/powerpoints_images/node28564/Slide29.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>29</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28624">Is it possible that for some diseases we need drugs that have multipl...</div></td>
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		<div id="div_30" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(30);">
			<span style="display:none;" id="span_30">|~|/files/powerpoints_images/node28564/Slide30.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>30</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28626"></div></td>
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		<div id="div_31" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(31);">
			<span style="display:none;" id="span_31">|~|/files/powerpoints_images/node28564/Slide31.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>31</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28628"></div></td>
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			<span style="display:none;" id="span_32">Targets of potential interest for the development of new calcium channel drugs.|~|/files/powerpoints_images/node28564/Slide32.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>32</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28630">Targets of potential interest for the development of new calcium chan...</div></td>
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<tr height="68px">
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		<div id="div_33" style="height: 68px; width: 300px; padding-top: 6px; cursor:hand;" class="cont_ents" onclick="fill_imagedetails(33);">
			<span style="display:none;" id="span_33">And ........it helps to have a champion  -someone who really believes in the project.   In this case - the late Albrecht Fleckenstein, Professor of Physiology, University of Freiburg, Germany.|~|/files/powerpoints_images/node28564/Slide33.JPG|~|563|~|422|~|0</span>
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														<td width="94%" align="left"><strong>Image</strong></td>
														<td width="6%"><strong>33</strong></td>
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														<td height="42" valign="top" colspan="2" align="left" text-align="left"><div id="imagedesc_28632">And ........it helps to have a champion  -someone who really believes...</div></td>
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A Case Study in Ion Channel Drug Discovery

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