WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 317146
Description: Indiplon is a nonbenzodiazepine, hypnotic sedative. Indiplon works by enhancing the action of the inhibitory neurotransmitter GABA, like most other nonbenzodiazepine sedatives. It primarily binds to the α1 subunits of the GABAA receptors in the brain. Indiplon was approved for the treatment of insomnia. Like other non-benzodiazepine hypnotics, its mechanism of action is to modulate subunits, especially the alpha-1 subunit, of the GABA receptor complex in order to induce sedation. Indiplon was developed in two different formulations to address two different types of insomnia complaint: indiplon-IR (immediate release) was designed for sleep onset difficulties, while indiplon-MR (modified release) was developed for sleep maintenance insomnia. While there are currently few peer reviewed articles about indiplon clinical trial results, the early information that is available seems to indicate that both formulations have been well tolerated and have proven effective at improving both patient reported and objectively measured sleep parameters in both adult and elderly insomnia patients. In May 2006, the FDA indicated that indiplon-IR was approvable and plans are to resubmit the application in 2007. Indiplon-MR was unapprovable and may require further evaluation.
MedKoo Cat#: 317146
Chemical Formula: C20H16N4O2S
Exact Mass: 376.0994
Molecular Weight: 376.43
Elemental Analysis: C, 63.81; H, 4.28; N, 14.88; O, 8.50; S, 8.52
Synonym: NBI-34060; NBI34060; NBI 34060; CL285,489; CL-285,489; CL 285,489; CL-285489; CL 285489; CL285489; Indiplon
IUPAC/Chemical Name: N-methyl-N-[3-[3-(thiophene-2-carbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]acetamide
InChi Key: CBIAWPMZSFFRGN-UHFFFAOYSA-N
InChi Code: InChI=1S/C20H16N4O2S/c1-13(25)23(2)15-6-3-5-14(11-15)17-8-9-21-20-16(12-22-24(17)20)19(26)18-7-4-10-27-18/h3-12H,1-2H3
SMILES Code: CC(N(C)C1=CC=CC(C2=CC=NC3=C(C(C4=CC=CS4)=O)C=NN23)=C1)=O
Appearance: 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, not in water
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
The following data is based on the product molecular weight 376.43 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.
|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|
1: Shimizu M, Fukami T, Ito Y, Kurokawa T, Kariya M, Nakajima M, Yokoi T. Indiplon is hydrolyzed by arylacetamide deacetylase in human liver. Drug Metab Dispos. 2014 Apr;42(4):751-8. doi: 10.1124/dmd.113.056184. Epub 2014 Jan 24. PubMed PMID: 24464802.
2: Xu L, Wang J, Xiao B, Yang J, Liu Y, Huang R. Preparation and characterization of a novel polymorph of indiplon, Form α. Bioorg Med Chem Lett. 2012 Jan 15;22(2):963-8. doi: 10.1016/j.bmcl.2011.12.013. Epub 2011 Dec 9. PubMed PMID: 22209207.
3: Lemon MD, Strain JD, Hegg AM, Farver DK. Indiplon in the management of insomnia. Drug Des Devel Ther. 2009 Sep 21;3:131-42. PubMed PMID: 19920929; PubMed Central PMCID: PMC2769245.
4: Marrs JC. Indiplon: a nonbenzodiazepine sedative-hypnotic for the treatment of insomnia. Ann Pharmacother. 2008 Jul;42(7):1070-9. doi: 10.1345/aph.1K683. Epub 2008 Jul 1. PubMed PMID: 18594049.
5: Farber RH, Burke PJ. Post-bedtime dosing with indiplon in adults and the elderly: results from two placebo-controlled, active comparator crossover studies in healthy volunteers. Curr Med Res Opin. 2008 Mar;24(3):837-46. doi: 10.1185/030079908X273327. Epub 2008 Feb 6. PubMed PMID: 18257978.
6: Roth T, Zammit GK, Scharf MB, Farber R. Efficacy and safety of as-needed, post bedtime dosing with indiplon in insomnia patients with chronic difficulty maintaining sleep. Sleep. 2007 Dec;30(12):1731-8. PubMed PMID: 18246982; PubMed Central PMCID: PMC2276136.
7: Lankford A. Indiplon in the treatment of sleep disorders. Neuropsychiatr Dis Treat. 2007 Dec;3(6):765-73. PubMed PMID: 19300612; PubMed Central PMCID: PMC2656319.
8: Wegner F, Deuther-Conrad W, Scheunemann M, Brust P, Fischer S, Hiller A, Diekers M, Strecker K, Wohlfarth K, Allgaier C, Steinbach J, Hoepping A. GABAA receptor pharmacology of fluorinated derivatives of the novel sedative-hypnotic pyrazolopyrimidine indiplon. Eur J Pharmacol. 2008 Feb 2;580(1-2):1-11. Epub 2007 Oct 22. PubMed PMID: 18035350.
9: Walsh JK, Moscovitch A, Burke J, Farber R, Roth T. Efficacy and tolerability of indiplon in older adults with primary insomnia. Sleep Med. 2007 Nov;8(7-8):753-9. Epub 2007 Sep 6. PubMed PMID: 17825616.
10: Rosenberg R, Roth T, Scharf MB, Lankford DA, Farber R. Efficacy and tolerability of indiplon in transient insomnia. J Clin Sleep Med. 2007 Jun 15;3(4):374-9. PubMed PMID: 17694726; PubMed Central PMCID: PMC1978303.
11: Madan A, Fisher A, Jin L, Chapman D, Bozigian HP. In vitro metabolism of indiplon and an assessment of its drug interaction potential. Xenobiotica. 2007 Jul;37(7):736-52. PubMed PMID: 17620220.
12: Hoepping A, Scheunemann M, Fischer S, Deuther-Conrad W, Hiller A, Wegner F, Diekers M, Steinbach J, Brust P. Radiosynthesis and biological evaluation of an 18F-labeled derivative of the novel pyrazolopyrimidine sedative-hypnotic agent indiplon. Nucl Med Biol. 2007 Jul;34(5):559-70. Epub 2007 Jun 8. PubMed PMID: 17591556.
13: Scharf MB, Black J, Hull S, Landin R, Farber R. Long-term nightly treatment with indiplon in adults with primary insomnia: results of a double-blind, placebo-controlled, 3-month study. Sleep. 2007 Jun;30(6):743-52. PubMed PMID: 17580596; PubMed Central PMCID: PMC1978349.
14: Lydiard RB, Lankford DA, Seiden DJ, Landin R, Farber R, Walsh JK. Efficacy and tolerability of modified-release indiplon in elderly patients with chronic insomnia: results of a 2-week double-blind, placebo-controlled trial. J Clin Sleep Med. 2006 Jul 15;2(3):309-15. PubMed PMID: 17561543.
15: Carter LP, Griffiths RR, Suess PE, Casada JH, Wallace CL, Roache JD. Relative abuse liability of indiplon and triazolam in humans: a comparison of psychomotor, subjective, and cognitive effects. J Pharmacol Exp Ther. 2007 Aug;322(2):749-59. Epub 2007 May 14. PubMed PMID: 17502431.
16: Lankford A, Ancoli-Israel S. Indiplon: the development of a novel therapy for the treatment of sleep onset and sleep maintenance insomnia. Int J Clin Pract. 2007 Jun;61(6):1037-45. Epub 2007 Mar 26. Review. PubMed PMID: 17386060.
17: Petroski RE, Pomeroy JE, Das R, Bowman H, Yang W, Chen AP, Foster AC. Indiplon is a high-affinity positive allosteric modulator with selectivity for alpha1 subunit-containing GABAA receptors. J Pharmacol Exp Ther. 2006 Apr;317(1):369-77. Epub 2006 Jan 6. PubMed PMID: 16399882.
18: Neubauer DN. Indiplon: the development of a new hypnotic. Expert Opin Investig Drugs. 2005 Oct;14(10):1269-76. Review. PubMed PMID: 16185169.
19: Sullivan SK, Petroski RE, Verge G, Gross RS, Foster AC, Grigoriadis DE. Characterization of the interaction of indiplon, a novel pyrazolopyrimidine sedative-hypnotic, with the GABAA receptor. J Pharmacol Exp Ther. 2004 Nov;311(2):537-46. Epub 2004 Jul 15. PubMed PMID: 15256540.
20: Foster AC, Pelleymounter MA, Cullen MJ, Lewis D, Joppa M, Chen TK, Bozigian HP, Gross RS, Gogas KR. In vivo pharmacological characterization of indiplon, a novel pyrazolopyrimidine sedative-hypnotic. J Pharmacol Exp Ther. 2004 Nov;311(2):547-59. Epub 2004 Jul 15. PubMed PMID: 15256538.