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20-September-2008 09:55:57 - IDRA-21 IDRA-21 Systematic IUPAC name 7-chloro-3-methyl-3,4-dihydro-2H-benzoe1,2,4thiadiazine 1,1-dioxide Identifiers CAS number 163936-78-5 ATC code ? PubChem 3688 Chemical data Formula C8H9ClN2O2S Mol. mass 232.68726 g/mol SMILES eMolecules PubChem Synonyms IDRA-21 Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Investigational New Medicine Routes ? IDRA-21 is an ampakine drug derived from aniracetam. IDRA-21 is a chiral molecule, with +-IDRA-21 being the active form.1 IDRA-21 shows nootropic effects in animal studies, significantly improving learning and memory. It is around 10-30x more potent than aniracetam in reversing cognitive deficits induced by alprazolam or scopolamine,23 and produces sustained effects lasting for up to three days after a single dose.4 The mechanism for this action is thought to be through promoting the induction of long-term potentiation between synapses in the brain.5 IDRA-21 does not produce neurotoxicity under normal conditions,6 although it may worsen neuronal damage following global ischemia after stroke or seizures.7 In comparison to the benzoylpiperidine derived ampakine drugs, IDRA-21 was more potent than CX-516, but less potent than CX-546.8 Newer benzothiadiazide derivatives with greatly increased potency compared to IDRA-21 have been developed,910 but these have not been researched to the same extent, with the benzoylpiperidine and benzoylpyrrolidine CX- series of drugs being favoured for clinical development, most likely due to more favourable toxicity profiles at high doses.11 References ^ Uzunov DP, Zivkovich I, Pirkle WH, Costa E, Guidotti A. Enantiomeric resolution with a new chiral stationary phase of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide, a cognition-enhancing benzothiadiazine derivative. Journal of Pharmaceutical Sciences. 1995 Aug;848:937-42. PMID 7500277 ^ Thompson DM, Guidotti A, DiBella M, Costa E. 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide IDRA 21, a congener of aniracetam, potently abates pharmacologically induced cognitive impairments in patas monkeys. Proceedings of the National Academy of Sciences U S A. 1995 Aug 15;9217:7667-71. PMID 7644474 ^ Zivkovic I, Thompson DM, Bertolino M, Uzunov D, DiBella M, Costa E, Guidotti A. 7-Chloro-3-methyl-3-4-dihydro-2H-1,2,4 benzothiadiazine S,S-dioxide IDRA 21: a benzothiadiazine derivative that enhances cognition by attenuating DL-alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid AMPA receptor desensitization. Journal of Pharmacology and Experimental Therapeutics. 1995 Jan;2721:300-9. PMID 7815345 ^ Buccafusco JJ, Weiser T, Winter K, Klinder K, Terry AV. The effects of IDRA 21, a positive modulator of the AMPA receptor, on delayed matching performance by young and aged rhesus monkeys. Neuropharmacology. 2004 Jan;461:10-22. PMID 14654093 ^ Arai A, Guidotti A, Costa E, Lynch G. Effect of the AMPA receptor modulator IDRA 21 on LTP in hippocampal slices. Neuroreport. 1996 Sep 2;713:2211-5. PMID 8930991 ^ Impagnatiello F, Oberto A, Longone P, Costa E, Guidotti A. 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide: a partial modulator of AMPA receptor desensitization devoid of neurotoxicity. Proceedings of the National Academy of Sciences U S A. 1997 Jun 24;9413:7053-8. PMID 9192690 ^ Yamada KA, Covey DF, Hsu CY, Hu R, Hu Y, He YY. The diazoxide derivative IDRA 21 enhances ischemic hippocampal neuron injury. Annals of Neurology. 1998 May;435:664-9. PMID 9585363 ^ Nagarajan N, Quast C, Boxall AR, Shahid M, Rosenmund C. Mechanism and impact of allosteric AMPA receptor modulation by the ampakine CX546. Neuropharmacology. 2001 Nov;416:650-63. PMID 11640919 ^ Phillips D, Sonnenberg J, Arai AC, Vaswani R, Krutzik PO, Kleisli T, Kessler M, Granger R, Lynch G, Richard Chamberlin A. 5'-alkyl-benzothiadiazides: a new subgroup of AMPA receptor modulators with improved affinity. Bioorganic and Medicinal Chemistry. 2002 May;105:1229-48. PMID 11886787 ^ Arai AC, Xia YF, Kessler M, Phillips D, Chamberlin R, Granger R, Lynch G. Effects of 5'-alkyl-benzothiadiazides on R,S-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid AMPA receptor biophysics and synaptic responses. Molecular Pharmacology. 2002 Sep;623:566-77. PMID 12181433 ^ Black MD. Therapeutic potential of positive AMPA modulators and their relationship to AMPA receptor subunits. A review of preclinical data. Psychopharmacology Berlin. 2005 Apr;1791:154-63. PMID 15672275 Tablets This pharmacology-related article is a stub. v d e Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics N06B Centrally acting sympathomimetics Amphetamine - Amphetaminil - Atomoxetine - Dextroamphetamine - Dextromethamphetamine - Fencamfamin - Fenozolone - Fenetylline - Methylphenidate - Mesocarb - Pemoline - Pipradrol - Prolintane Xanthine derivatives Caffeine - Propentofylline Glutamate receptor Racetams Aniracetam - Nefiracetam - Oxiracetam - Phenylpiracetam - Piracetam - Pramiracetam Ampakines CX-516 - CX-546 - CX-614 - CX-691 - CX-717 - IDRA-21 - LY-503,430 - PEPA Eugeroics / Benzhydryl compounds Adrafinil - Armodafinil - Modafinil Histamine H3 receptor antagonists ABT-239 - Ciproxifan Other psychostimulants and nootropics Acetylcarnitine - Citicoline - Cyprodenate - Idebenone - Ispronicline - Deanol - Dimebon - Fipexide - Linopirdine - Meclofenoxate - Nizofenone - Pirisudanol - Pyritinol - Sulbutiamine - Taltirelin - Tricyanoaminopropene - Vinpocetine v d e Glutamate receptor ligands Ionotropic NMDA Agonists; NMDA Tetrazolylglycine Antagonists; Competitive antagonists; AP7 APV CGP-37849 Midafotel CPPene PEAQX Perzinfotel PPDA Sdz 220-581 Selfotel; Noncompetitive antagonists; Aptiganel Dizocilpine FPL-12495 FR-115,427 Gacyclidine Hodgkinsine HU-211 Indantadol Psychotridine Remacemide; Uncompetitive channel blockers; 2-MDP Amantadine Budipine Delucemine Dexoxadrol Dextromethorphan Dextrorphan Endopsychosin Etoxadrol Eticyclidine Ibogaine Ketamine Memantine Neramexane Nitrous oxide Phencyclidine Rhynchophylline Riluzole Rolicyclidine Tenocyclidine Tiletamine Xenon; Glycine site antagonists; 1-Aminocyclopropanecarboxylic acid ACEA-1021 7-Chlorokynurenate CGP-39653 DCKA Gavestinel GV-150,526 Kynurenic acid L-689,560 ZD-9379; Polyamine site antagonists; Besonprodil CP-101,606 Eliprodil Ifenprodil Ro25-6981 Traxoprodil; Indirect antagonists; Lubeluzole AMPA Agonists; AMPA Domoic acid 5-Fluorowillardiine; Positive allosteric modulators; Aniracetam Cyclothiazide CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-392,098 LY-404,187 LY-451,646 LY-503,430 Oxiracetam PEPA Piracetam Pramiracetam Antagonists; ATPO CNQX DNQX NBQX Tezampanel LY-293,558; Negative allosteric modulators; GYKI-53,655 Kainate Agonists; 5-Iodowillardiine ATPA Domoic acid Kainic acid LY-339,434 SYM-2081 Antagonists; CNQX DNQX LY-382,884 NBQX NS102 UBP-302; Negative allosteric modulators; NS-3763 Metabotropic Group I Agonists; Unselective; ACPD Dihydroxyphenylglycine; mGlu1 selective; Ro01-6128; mGlu5 selective; CHPG DFB Antagonists; Unselective; MCPG; mGlu1 selective; BAY 36-7620 CPCCOEt LY-367,385; mGlu5 selective; LY-344,545 MPEP MTEP Group II Agonists; Eglumegad LY-354,740 LY-487,379 Antagonists; EGLU LY-341,495 Group III Agonists; Unselective; AP4; mGlu4 selective; PHCCC; mGlu8 selective; DCPG Antagonists; CPPG UBP-1112 Retrieved from http://en..org/wiki/IDRA-21 Categories: Pharmacology stubs | Ampakines Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 20 June 2008, at 05:48
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