MedKoo Cat#: 317146 | Name: Indiplon
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Indiplon
Indiplon
CAS#325715-02-4

Theoretical Analysis

MedKoo Cat#: 317146

Name: Indiplon

CAS#: 325715-02-4

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

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 weeks
50mg USD 450.00 2 weeks
100mg USD 750.00 2 weeks
200mg USD 1,250.00 2 weeks
500mg USD 2,650.00 2 weeks
1g USD 3,650.00 2 weeks
2g USD 6,250.00 2 weeks
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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
More Info
Product Data
Biological target:
Positive allosteric modulator of GABAA; acts at benzodiazepine site.
In vitro activity:
Likewise, a reduction to 46.7% and 14.9% in the percentage of inhibition with Indiplon 125 μM and 10 μM was obtained, respectively (Fig. 2). Under these conditions, Indiplon inhibited the platelet aggregation induced by ADP in a concentration-dependent manner with an estimated IC50 of 260 μM. Reference: Biomed Pharmacother. 2019 Mar;111:378-385. https://pubmed.ncbi.nlm.nih.gov/30594050/
In vivo activity:
Relative to aCSF controls, PFC infusion of Indiplon significantly reduced the freezing response in MK-801-treated rats to control levels (Fig. 6b). Collectively, the results provide a mechanistic link between deficits in prefrontal GABAergic function and the age-dependent behavioral disruption observed following adolescent MK-801 exposure. Reference: J Neurosci. 2020 Jun 17;40(25):4881-4887. https://pubmed.ncbi.nlm.nih.gov/32430298/
Solvent mg/mL mM
Solubility
DMF 25.0 66.41
DMF:PBS (pH 7.2) (1:1) 0.5 1.33
DMSO 14.0 37.19
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

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
Formulation protocol:
1. Burgos CF, Sanchéz C, Sepúlveda C, Fuentes E, Palomo I, Alarcón M. Anti-aggregation effect on platelets of Indiplon a hypnotic sedative non-benzodiazepine drug. Biomed Pharmacother. 2019 Mar;111:378-385. doi: 10.1016/j.biopha.2018.12.087. Epub 2018 Dec 26. PMID: 30594050. 2. Flores-Barrera E, Thomases DR, Tseng KY. MK-801 Exposure during Adolescence Elicits Enduring Disruption of Prefrontal E-I Balance and Its Control of Fear Extinction Behavior. J Neurosci. 2020 Jun 17;40(25):4881-4887. doi: 10.1523/JNEUROSCI.0581-20.2020. Epub 2020 May 19. PMID: 32430298; PMCID: PMC7326362. 3. Nys J, Smolders K, Laramée ME, Hofman I, Hu TT, Arckens L. Regional Specificity of GABAergic Regulation of Cross-Modal Plasticity in Mouse Visual Cortex after Unilateral Enucleation. J Neurosci. 2015 Aug 12;35(32):11174-89. doi: 10.1523/JNEUROSCI.3808-14.2015. PMID: 26269628; PMCID: PMC6605129.
In vitro protocol:
1. Burgos CF, Sanchéz C, Sepúlveda C, Fuentes E, Palomo I, Alarcón M. Anti-aggregation effect on platelets of Indiplon a hypnotic sedative non-benzodiazepine drug. Biomed Pharmacother. 2019 Mar;111:378-385. doi: 10.1016/j.biopha.2018.12.087. Epub 2018 Dec 26. PMID: 30594050.
In vivo protocol:
1. Flores-Barrera E, Thomases DR, Tseng KY. MK-801 Exposure during Adolescence Elicits Enduring Disruption of Prefrontal E-I Balance and Its Control of Fear Extinction Behavior. J Neurosci. 2020 Jun 17;40(25):4881-4887. doi: 10.1523/JNEUROSCI.0581-20.2020. Epub 2020 May 19. PMID: 32430298; PMCID: PMC7326362. 2. Nys J, Smolders K, Laramée ME, Hofman I, Hu TT, Arckens L. Regional Specificity of GABAergic Regulation of Cross-Modal Plasticity in Mouse Visual Cortex after Unilateral Enucleation. J Neurosci. 2015 Aug 12;35(32):11174-89. doi: 10.1523/JNEUROSCI.3808-14.2015. PMID: 26269628; PMCID: PMC6605129.
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.