IDRA-21
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MedKoo CAT#: 530569

CAS#: 22503-72-6

Description: IDRA-21 is a positive AMPA receptor modulator. IDRA-21 inhibits synaptic and extrasynaptic NMDA receptor mediated events in cultured cerebellar granule cells. IDRA 21 enhances ischemic hippocampal neuron injury.


Chemical Structure

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IDRA-21
CAS# 22503-72-6

Theoretical Analysis

MedKoo Cat#: 530569
Name: IDRA-21
CAS#: 22503-72-6
Chemical Formula: C8H9ClN2O2S
Exact Mass: 232.0073
Molecular Weight: 232.682
Elemental Analysis: C, 41.30; H, 3.90; Cl, 15.24; N, 12.04; O, 13.75; S, 13.78

Price and Availability

Size Price Availability Quantity
100.0mg USD 250.0 2 Weeks
200.0mg USD 450.0 2 Weeks
500.0mg USD 950.0 2 Weeks
1.0g USD 1750.0 2 Weeks
2.0g USD 2950.0 2 Weeks
5.0g USD 4950.0 2 Weeks
10.0g USD 5950.0 2 Weeks
20.0g USD 8950.0 2 Weeks
50.0g USD 16550.0 2 Weeks
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Synonym: IDRA-21; IDRA 21; IDRA21.

IUPAC/Chemical Name: 7-Chloro-3-methyl-3-4-dihydro-2H-1,2,4 benzothiadiazine S,S-dioxide

InChi Key: VZRNTCHTJRLTMU-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H9ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-5,10-11H,1H3

SMILES Code: CC(NC1=CC=C(Cl)C=C12)NS2(=O)=O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 232.682 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Malkova L, Kozikowski AP, Gale K. The effects of huperzine A and IDRA 21 on visual recognition memory in young macaques. Neuropharmacology. 2011 Jun;60(7-8):1262-8. doi: 10.1016/j.neuropharm.2010.12.018. Epub 2010 Dec 23. PubMed PMID: 21185313; PubMed Central PMCID: PMC3073152.

2: 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;46(1):10-22. PubMed PMID: 14654093.

3: Losi G, Puia G, Braghiroli D, Baraldi M. IDRA-21, a positive AMPA receptor modulator, inhibits synaptic and extrasynaptic NMDA receptor mediated events in cultured cerebellar granule cells. Neuropharmacology. 2004 Jun;46(8):1105-13. PubMed PMID: 15111017.

4: Yamada KA, Covey DF, Hsu CY, Hu R, Hu Y, He YY. The diazoxide derivative IDRA 21 enhances ischemic hippocampal neuron injury. Ann Neurol. 1998 May;43(5):664-9. PubMed PMID: 9585363.

5: Krintel C, Frydenvang K, Olsen L, Kristensen MT, de Barrios O, Naur P, Francotte P, Pirotte B, Gajhede M, Kastrup JS. Thermodynamics and structural analysis of positive allosteric modulation of the ionotropic glutamate receptor GluA2. Biochem J. 2012 Jan 1;441(1):173-8. doi: 10.1042/BJ20111221. PubMed PMID: 21895609.

6: Ptak CP, Ahmed AH, Oswald RE. Probing the allosteric modulator binding site of GluR2 with thiazide derivatives. Biochemistry. 2009 Sep 15;48(36):8594-602. doi: 10.1021/bi901127s. PubMed PMID: 19673491; PubMed Central PMCID: PMC2756660.

7: 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. J Pharmacol Exp Ther. 1995 Jan;272(1):300-9. PubMed PMID: 7815345.

8: 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. Proc Natl Acad Sci U S A. 1995 Aug 15;92(17):7667-71. PubMed PMID: 7644474; PubMed Central PMCID: PMC41206.

9: 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;7(13):2211-5. PubMed PMID: 8930991.

10: 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. Bioorg Med Chem. 2002 May;10(5):1229-48. PubMed PMID: 11886787.

11: Puia G, Losi G, Razzini G, Braghiroli D, Di Bella M, Baraldi M. Modulation of kainate--activated currents by diazoxide and cyclothiazide analogues (IDRA) in cerebellar granule neurons. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):1007-15. PubMed PMID: 11041540.

12: 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. Proc Natl Acad Sci U S A. 1997 Jun 24;94(13):7053-8. PubMed PMID: 9192690; PubMed Central PMCID: PMC21283.

13: Padmanabhan B. Identification of novel modulators for ionotropic glutamate receptor, iGluA2 by in-silico screening. Theor Biol Med Model. 2013 Jul 15;10:46. doi: 10.1186/1742-4682-10-46. PubMed PMID: 23855825; PubMed Central PMCID: PMC3718743.

14: Vandesquille M, Carrié I, Louis C, Beracochea D, Lestage P. Effects of positive modulators of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)-type glutamate receptors in a benzodiazepine-induced deficit of spatial discrimination in mice. J Psychopharmacol. 2012 Jun;26(6):845-56. doi: 10.1177/0269881111416692. Epub 2011 Sep 2. PubMed PMID: 21890586.

15: 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. Mol Pharmacol. 2002 Sep;62(3):566-77. PubMed PMID: 12181433.

16: 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;41(6):650-63. PubMed PMID: 11640919.

17: Lockhart BP, Rodriguez M, Mourlevat S, Peron P, Catesson S, Villain N, Galizzi JP, Boutin JA, Lestage P. S18986: a positive modulator of AMPA-receptors enhances (S)-AMPA-mediated BDNF mRNA and protein expression in rat primary cortical neuronal cultures. Eur J Pharmacol. 2007 Apr 30;561(1-3):23-31. Epub 2007 Feb 1. PubMed PMID: 17331496.

18: 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. J Pharm Sci. 1995 Aug;84(8):937-42. PubMed PMID: 7500277.

19: Kertész S, Kapus G, Lévay G. Interactions of allosteric modulators of AMPA/kainate receptors on spreading depression in the chicken retina. Brain Res. 2004 Oct 29;1025(1-2):123-9. PubMed PMID: 15464752.

20: Cannazza G, Jozwiak K, Parenti C, Braghiroli D, Carrozzo MM, Puia G, Losi G, Baraldi M, Lindner W, Wainer IW. A novel class of allosteric modulators of AMPA/Kainate receptors. Bioorg Med Chem Lett. 2009 Feb 15;19(4):1254-7. doi: 10.1016/j.bmcl.2008.12.094. Epub 2008 Dec 30. PubMed PMID: 19162477; PubMed Central PMCID: PMC2656388.

IDRA-21

100.0mg / USD 250.0