Rimantadine

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(New page: <applet load="" size="480" color="" frame="true" spin="on" Scene ="Tacrine/Tacrine/3" align="right" caption="Tacrine, also known as Cognex"/> ===Better Known as: Cognex=== * Marketed By...)
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<applet load="" size="480" color="" frame="true" spin="on" Scene ="Tacrine/Tacrine/3" align="right" caption="Tacrine, also known as Cognex"/>
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<StructureSection load='' size='340' side='right' caption='Rimantadine, also known as Flumadine, ([[2rlf]])' scene='Rimantadine/Rimantainde/1'>
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===Better Known as: Cognex===
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===Better Known as: Flumadine===
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* Marketed By: Parke Davis Pharmaceuticals <br />
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* Marketed By: Forest Labs<br />
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* Major Indication: [[Alzheimer's Disease]]<br />
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* Major Indication: [[Influenza]] Infection<br />
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* Drug Class: [[Acetylcholinesterase]] Inhibitor
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* Drug Class: [[M2 Proton Channel]] Inhibitor
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* Date of FDA Approval (Patent Expiration): 1993 (N/A)<br />
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* Date of FDA Approval (Patent Expiration): 1993 (2001)<br />
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* 1994 Sales: $100 Million
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* 1994 Sales: N/A
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* Importance: One of the the first treatments for the symptoms of [[Alzheimer's Disease]], although no definitive proof exists as to whether it alters the progression of the disease.
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* Importance: One of the the first treatments for [[Influenza]] Infections. Since 1994, nearly 100% of influenza viruses had developed resistance to rimantadine, and it is no longer recommended as a treatment for the flu.
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* The following is a list of Pharmacokinetic Parameters. See: [[Pharmaceutical Drugs]] for more information
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* See [[Pharmaceutical Drugs]] for more information about other drugs and disorders.
===Mechanism of Action===
===Mechanism of Action===
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Tacrine is an [[Acetylcholinesterase]] (AChE) inhibitor. It binds to the active site of <scene name='Tacrine/Ache/1'>AChE</scene>, utilizing many of the same residues which <scene name='Tacrine/Ac/1'>bind and break down acetylcholine</scene>. By inhibiting AChE, the important neurotransmitter, [[acetylcholine]], is degraded at a slower rate, helping reverse the marked decrease in neuronal function evident in [[Alzheimer's Disease]] patients. Tacrine <scene name='Tacrine/Bound/2'>primarily interacts with residues</scene> Phe 330, His 440, Trp 84, & Ser 200 in tightly binding to the AChE binding site via pi stacking interactions. It is clearly visible how <scene name='Tacrine/Inter/3'>Tacrine interferes</scene> with the binding of acetylcholine, outcompeting acetylcholine for nearly the same space in the active site. <ref>PMID:8415649</ref>
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The [[Influenza]] A Virus viral envelope is dotted with various [[ion channels]] including [[M2 Proton Channel|M2 Proton Channels]]. The <scene name='Rimantadine/M2/1'>M2 protein</scene> plays a critical role in the life cycle of the Influenza virus. It enables hydrogen ions to enter the virion form the endosome. The result of this is a more acidic environment within the virus, causing dissociation of the viral matrix protein M1 from the ribonucleoprotein RNP. Dissociation of the viral matrix protein is a crucial step in uncoating of the virus and exposing its contents to the cytoplasm of the host cell, allowing the virus to hijack the cellular machinery to replicate. <scene name='Rimantadine/Four/1'>Rimantadine binds in multiple places</scene> outside the pore formed by the M2 protein, <scene name='Rimantadine/M2b/1'>utilizing residues</scene> Leu 43, Leu 40, Asp 44, Arg 45, Trp 41 from one chain and Ile 42 from the neighboring chain. This effectively disables the protein from transferring protons into the viral particle.<ref>PMID: 18235503</ref>
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</StructureSection>
===Pharmacokinetics===
===Pharmacokinetics===
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{| class="wikitable" border="1" width="52%" style="text-align:center"
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<table style="background: cellspacing="0px" align="" cellpadding="0px" width="42%">
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|-
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<tr>
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! colspan="7" align="center"| M2 Proton Channel Inhibitor [[Pharmaceutical_Drugs#Pharmacokinetics_Translated|Pharmacokinetics]]<ref>PMID:3662473</ref>
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<td style="width:100%; vertical-align:top;border-width:0px; border-style:inset">
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|-
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<div style="height:100%; width: 100%">
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! Parameter
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{{:M2 Proton Channel Inhibitor Pharmacokinetics}}
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! [[Rimantadine]]
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</div>
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! [[Amantadine]]
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</td>
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|-
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</tr>
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! [[Pharmaceutical_Drugs#Tmax|T<sub>max</sub>]] (hr)
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</table>
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! 4.3
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Cmax|C<sub>max</sub>]] (ng/ml)
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! 310
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Bioavailability_.28F.29|Bioavailability]] (%)
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! [[Rimantadine]]
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Protein_Binding|Protein Binding]] (%)
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! [[Rimantadine]]
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Half_Life_.28T1.2F2.29|T<sub>1/2</sub>]] (hr)
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! 27.7
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Area_Under_the_Curve_.28AUC.29|AUC]] (ng/ml/hr)
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! 11917
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Clearance_.28Cl.29|Clearance]] (L/h)
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! [[Rimantadine]]
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! [[Amantadine]]
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|-
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! [[Pharmaceutical_Drugs#Inhibitory_Concentration_.28IC50.29|IC<sub>50</sub>]] (nM)
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! [[Rimantadine]]
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! [[Amantadine]]
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|-
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! Dosage (mg)
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! 100
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! [[Amantadine]]
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|-
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! Metabolism
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! [[Rimantadine]]
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! [[Amantadine]]
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|}
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===References===
===References===

Current revision

Rimantadine, also known as Flumadine, (2rlf)

Drag the structure with the mouse to rotate

Pharmacokinetics

M2 Proton Channel Inhibitor Pharmacokinetics
Parameter Rimantadine Amantadine
Tmax (hr) 4.3 2.5
Cmax (ng/ml) 310 402
Bioavailability (%) >90 >90
Protein Binding (%) 40 67
T1/2 (hr) 27.7 ~15
AUC (ng/ml/hr) 11917 5420
Dosage (mg) 100 100
Metabolism Negligible Negligible

For Pharmacokinetic Data References, See: References

References

  1. ↑ Schnell JR, Chou JJ. Structure and mechanism of the M2 proton channel of influenza A virus. Nature. 2008 Jan 31;451(7178):591-5. PMID:18235503 doi:10.1038/nature06531


Proteopedia Page Contributors and Editors (what is this?)

David Canner, Alexander Berchansky

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