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'''Zosuquidar''' is an experimental [[antineoplastic]] [[drug]] currently under development. It has completed [[Phases of clinical research|Phase 3]] clinical trials in the United States. It [[Enzyme inhibition|inhibits]] [[P-glycoprotein]]s. Other drugs with this mechanism include [[tariquidar]] and [[laniquidar]]. P-glycoproteins are trans-membrane [[protein]]s that pump foreign substances out of cells in an [[Adenosine triphosphate|ATP]] dependent fashion. Cancers overexpressing P-glycoproteins are able to pump out therapeutic molecules before they are able to reach their target, effectively making the cancer multi-drug resistant. Zosuquidar inhibits P-glycoproteins, inhibiting the efflux pump and restoring sensitivity to chemotherapeutic agents. |
'''Zosuquidar''' is an experimental [[antineoplastic]] [[drug]] currently under development. It has completed [[Phases of clinical research|Phase 3]] clinical trials in the United States. It [[Enzyme inhibition|inhibits]] [[P-glycoprotein]]s. Other drugs with this mechanism include [[tariquidar]] and [[laniquidar]]. P-glycoproteins are trans-membrane [[protein]]s that pump foreign substances out of cells in an [[Adenosine triphosphate|ATP]] dependent fashion. Cancers overexpressing P-glycoproteins are able to pump out therapeutic molecules before they are able to reach their target, effectively making the cancer multi-drug resistant. Zosuquidar inhibits P-glycoproteins, inhibiting the efflux pump and restoring sensitivity to chemotherapeutic agents. |
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==Chemistry== |
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[[File:Zosuquidar synthesis.png|700px]] |
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Reaction of [[dibenzosuberone]] (1) with the [[difluorocarbene]] from [[chlorodifluoroacetate]] (2) affords the cyclopropyl adduct (3). Reduction of the ketone with borohydride proceeds to afford the derivative wherein the fused cyclpropyl and alcohol are on the same side of the seven-membered ring (4). The carbinol is then converted to the halide with thionyl chloride apparently with retention of configuration (5). Displacement with piperazine monoformamide (6) leads to the alkylated product in which the groups are now anti. Hydrolysis of the formamide grouping then affords secondary amine (7). In a convergent sequence, [[5-hydroxyquinoline]] (8) is allowed to react with the tosyl derivative of chiral [[glycidol]] (9), thus affording the final product in good yield.<ref>{{Cite doi|10.1016/0960-894X(95)00426-T}}</ref> |
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==References== |
==References== |
Revision as of 10:53, 8 April 2015
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ECHA InfoCard | 100.236.552 |
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Formula | C32H31F2N3O2 |
Molar mass | 527.61 g/mol g·mol−1 |
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Zosuquidar is an experimental antineoplastic drug currently under development. It has completed Phase 3 clinical trials in the United States. It inhibits P-glycoproteins. Other drugs with this mechanism include tariquidar and laniquidar. P-glycoproteins are trans-membrane proteins that pump foreign substances out of cells in an ATP dependent fashion. Cancers overexpressing P-glycoproteins are able to pump out therapeutic molecules before they are able to reach their target, effectively making the cancer multi-drug resistant. Zosuquidar inhibits P-glycoproteins, inhibiting the efflux pump and restoring sensitivity to chemotherapeutic agents.