Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H16N4O2S |
| Molecular Weight | 376.432 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C(C)=O)C1=CC(=CC=C1)C2=CC=NC3=C(C=NN23)C(=O)C4=CC=CS4
InChI
InChIKey=CBIAWPMZSFFRGN-UHFFFAOYSA-N
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
DescriptionCurator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800010511
https://en.wikipedia.org/wiki/Indiplon
Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800010511
https://en.wikipedia.org/wiki/Indiplon
Indiplon is a nonbenzodiazepine, hypnotic sedative that was proposed for the treatment of insomnia. It is a high-affinity allosteric potentiator of GABAA responses that demonstrates preference for α1 subunit-containing GABAA receptors. There is minimal potential for adverse effects, residual daytime sedation, tolerance, respiratory depression. The simultaneous administration of indiplon and alcohol did not result in any significant pharmacokinetic changes. There is little risk of pharmacokinetic interaction between indiplon and any co-administered drugs. Developer (Neurocrine) decided to discontinue all clinical and marketing development of Indiplon in the United States.
CNS Activity
Approval Year
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 h |
single, oral |
INDIPLON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDIPLON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Somnolence, Headache... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | 6.7% | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Somnolence | 7.8% | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Indiplon. Indiplon modified-release, indiplon MR, NBI 34060, NBI 34060 modified-release, NBI 34060 MR. | 2002 |
|
| Gaboxadol: in vitro interaction studies with benzodiazepines and ethanol suggest functional selectivity. | 2003 Apr 25 |
|
| Rotarod studies in the rat of the GABAA receptor agonist gaboxadol: lack of ethanol potentiation and benzodiazepine cross-tolerance. | 2003 Dec 15 |
|
| Neurocrine Biosciences, Inc. Soporific science. | 2003 May |
|
| Gateways to clinical trials. | 2003 Oct |
|
| Sleeping pills without regrets. They've long been the risky quick fixes of sleep medicine. Soon some sleeping pills may be sold as long-term solutions. | 2004 Aug |
|
| Gateways to clinical trials. | 2004 Dec |
|
| Characterization of the interaction of indiplon, a novel pyrazolopyrimidine sedative-hypnotic, with the GABAA receptor. | 2004 Nov |
|
| In vivo pharmacological characterization of indiplon, a novel pyrazolopyrimidine sedative-hypnotic. | 2004 Nov |
|
| Gateways to clinical trials. | 2004 Oct |
|
| Sleep disturbances, psychiatric disorders, and psychotropic drugs. | 2005 |
|
| Gateways to clinical trials. | 2005 Apr |
|
| Gateways to clinical trials. | 2005 Jul-Aug |
|
| Gateways to clinical trials. | 2005 Oct |
|
| Indiplon: the development of a new hypnotic. | 2005 Oct |
|
| Gateways to clinical trials. | 2005 Sep |
|
| Gateways to clinical trials. | 2006 Dec |
|
| Efficacy and tolerability of modified-release indiplon in elderly patients with chronic insomnia: results of a 2-week double-blind, placebo-controlled trial. | 2006 Jul 15 |
|
| The new cancer fighter (and other hot drugs on the way). | 2006 Mar 20 |
|
| Gateways to clinical trials. | 2006 Oct |
|
| Relative abuse liability of indiplon and triazolam in humans: a comparison of psychomotor, subjective, and cognitive effects. | 2007 Aug |
|
| Efficacy and safety of as-needed, post bedtime dosing with indiplon in insomnia patients with chronic difficulty maintaining sleep. | 2007 Dec |
|
| Auto-modulation of neuroactive steroids on GABA A receptors: a novel pharmacological effect. | 2007 Feb |
|
| [Recent and potential drugs for treatment of insomnia]. | 2007 Jan |
|
| New perspectives for the treatment of disorders of sleep and arousal. | 2007 Jul |
|
| Radiosynthesis and biological evaluation of an 18F-labeled derivative of the novel pyrazolopyrimidine sedative-hypnotic agent indiplon. | 2007 Jul |
|
| Lack of generalisation between the GABAA receptor agonist, gaboxadol, and allosteric modulators of the benzodiazepine binding site in the rat drug discrimination procedure. | 2007 Jul |
|
| Long-term nightly treatment with indiplon in adults with primary insomnia: results of a double-blind, placebo-controlled, 3-month study. | 2007 Jun |
|
| Indiplon: the development of a novel therapy for the treatment of sleep onset and sleep maintenance insomnia. | 2007 Jun |
|
| Gaboxadol, a selective extrasynaptic GABA(A) agonist, does not generalise to other sleep-enhancing drugs: a rat drug discrimination study. | 2007 Mar |
|
| GABAA receptor pharmacology of fluorinated derivatives of the novel sedative-hypnotic pyrazolopyrimidine indiplon. | 2008 Feb 2 |
|
| Indiplon: a nonbenzodiazepine sedative-hypnotic for the treatment of insomnia. | 2008 Jul |
|
| Discriminative stimulus effects of tiagabine and related GABAergic drugs in rats. | 2008 May |
Sample Use Guides
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C28197
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NCI_THESAURUS |
C29756
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CHEMBL262075
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6450813
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m6254
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DTXSID80186270
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8200
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300000034229
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DB12590
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8BT63DA42E
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325715-02-4
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Indiplon
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MM-52
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C74385
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C469870
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ACTIVE MOIETY
