INDIPLON

Investigational

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C20H16N4O2S
Molecular Weight	376.432
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16185169
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA receptor alpha-1 subunit 19 Target ID: CHEMBL1962 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16185169 \| https://www.ncbi.nlm.nih.gov/pubmed/16399882	Positive Allosteric Modulator 186		2.6 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16185169 https://www.ncbi.nlm.nih.gov/pubmed/18246982	Primary		Phase III 665	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.5 h REVIEW https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1978303/	single, oral		INDIPLON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2 h REVIEW https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1978303/	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: https://pubmed.ncbi.nlm.nih.gov/18246982	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18246982	Other AEs: Somnolence, Headache... Other AEs: Somnolence (7.8%) Headache (6.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/18246982

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: https://pubmed.ncbi.nlm.nih.gov/18246982	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18246982
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: https://pubmed.ncbi.nlm.nih.gov/18246982	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18246982

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00C6ZW	https://www.1pchem.com/search?query=1P00C6ZW
Alfa Chemistry	25069	http://www.alfa-chemistry.com/search.aspx?q=25069
Alfa Chemistry	ACM1001083379	http://www.alfa-chemistry.com/search.aspx?q=ACM1001083379
Angene	AGN-PC-0WH2DI	http://www.angenechemical.com/productshow/AGN-PC-0WH2DI.html
Axon MedChem	1121	https://www.axonmedchem.com/product/1121
BOC Sciences	325715-02-4	http://www.bocsci.com/description.asp?cas=325715-02-4
Capot Chemical	25604	https://www.capotchem.com/search.do?q=25604
Cayman Chemical	11638	http://www.caymanchem.com/app/template/Product.vm/catalog/11638
eMolecules	10705189	https://orderbb.emolecules.com/search/#?query=10705189
Hairui	HR148973	http://www.hairuichem.com/en/product/search.do?q=HR148973
mcule	MCULE-5857056440	https://mcule.com/MCULE-5857056440/
Molnova	M14055	https://www.molnova.com/en/serch-list.html?keywords=M14055
MuseChem	R048117	https://www.musechem.com/product/R048117.html
Princeton BioMolecular Research	PBMR221877	http://www.princetonbio.com/order_online?common_id=PBMR221877
ShangHai Biochempartner	BCP04475	http://www.biochempartner.com/search_BCP04475
Tocris	3597	https://www.tocris.com/search.php?Type=QuickSearch&Value=3597
Toronto Research Chemicals	I527200	https://www.trc-canada.com/product-detail/?CatNum=I527200
Wonderchem	WD05W1O	http://www.wonder-chem.com/search.html?text=WD05W1O

PubMed

Title	Date	PubMed
The societal costs of insomnia.	2010-12-20	21326650
[The newer sedative-hypnotics].	2010-09	20945020
Diagnosis and treatment of chronic insomnia.	2010-04	20814491
Indiplon in the management of insomnia.	2009-09-21	19920929
Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders.	2009	19228178
Gateways to clinical trials.	2008-09	18985183
Indiplon: a nonbenzodiazepine sedative-hypnotic for the treatment of insomnia.	2008-07	18594049
Gaboxadol -- a different hypnotic profile with no tolerance to sleep EEG and sedative effects after repeated daily dosing.	2008-07	18304623
Discriminative stimulus effects of tiagabine and related GABAergic drugs in rats.	2008-05	18264695
Post-bedtime dosing with indiplon in adults and the elderly: results from two placebo-controlled, active comparator crossover studies in healthy volunteers.	2008-03	18257978
[New hypnotics: perspectives from sleep physiology].	2008-02-13	18265473
GABAA receptor pharmacology of fluorinated derivatives of the novel sedative-hypnotic pyrazolopyrimidine indiplon.	2008-02-02	18035350
Indiplon in the treatment of sleep disorders.	2007-12	19300612
Efficacy and safety of as-needed, post bedtime dosing with indiplon in insomnia patients with chronic difficulty maintaining sleep.	2007-12	18246982
Efficacy and tolerability of indiplon in older adults with primary insomnia.	2007-11	17825616
Relative abuse liability of indiplon and triazolam in humans: a comparison of psychomotor, subjective, and cognitive effects.	2007-08	17502431
New perspectives for the treatment of disorders of sleep and arousal.	2007-07	17652996
In vitro metabolism of indiplon and an assessment of its drug interaction potential.	2007-07	17620220
Radiosynthesis and biological evaluation of an 18F-labeled derivative of the novel pyrazolopyrimidine sedative-hypnotic agent indiplon.	2007-07	17591556
Lack of generalisation between the GABAA receptor agonist, gaboxadol, and allosteric modulators of the benzodiazepine binding site in the rat drug discrimination procedure.	2007-07	17361395
Efficacy and tolerability of indiplon in transient insomnia.	2007-06-15	17694726
Long-term nightly treatment with indiplon in adults with primary insomnia: results of a double-blind, placebo-controlled, 3-month study.	2007-06	17580596
Will insomnia treatments produce overall cost savings to commercial managed-care plans? A predictive analysis in the United States.	2007-06	17559740
Indiplon: the development of a novel therapy for the treatment of sleep onset and sleep maintenance insomnia.	2007-06	17386060
Gaboxadol, a selective extrasynaptic GABA(A) agonist, does not generalise to other sleep-enhancing drugs: a rat drug discrimination study.	2007-03	17196996
Auto-modulation of neuroactive steroids on GABA A receptors: a novel pharmacological effect.	2007-02	17084864
[Recent and potential drugs for treatment of insomnia].	2007-01	17220574
Gateways to clinical trials.	2006-12	17235418
Gateways to clinical trials.	2006-10	17136234
Gateways to clinical trials.	2006-09	17003851
Gateways to clinical trials.	2006-08-09	16894408
Synthesis, pharmacology and molecular modeling of N-substituted 2-phenyl-indoles and benzimidazoles as potent GABA(A) agonists.	2006-08	16764969
Efficacy and tolerability of modified-release indiplon in elderly patients with chronic insomnia: results of a 2-week double-blind, placebo-controlled trial.	2006-07-15	17561543
Insomnia in the elderly: cause, approach, and treatment.	2006-06	16750956
Indiplon is a high-affinity positive allosteric modulator with selectivity for alpha1 subunit-containing GABAA receptors.	2006-04	16399882
The new cancer fighter (and other hot drugs on the way).	2006-03-20	17621712
Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs.	2005-11	16095764
Gateways to clinical trials.	2005-10	16273137
Indiplon: the development of a new hypnotic.	2005-10	16185169
Gateways to clinical trials.	2005-09-24	16179960
Gateways to clinical trials.	2005-09	16258596
Diagnosis and management of insomnia in older people.	2005-07	15982376
Gateways to clinical trials.	2005-04	15834452
Sleep disturbances, psychiatric disorders, and psychotropic drugs.	2005	16416708
Sleep and aging: prevalence of disturbed sleep and treatment considerations in older adults.	2005	16336039
Gateways to clinical trials.	2004-12	15672123
Characterization of the interaction of indiplon, a novel pyrazolopyrimidine sedative-hypnotic, with the GABAA receptor.	2004-11	15256540
Gateways to clinical trials.	2004-10	15605126
Gateways to clinical trials.	2004-09-07	15349141
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.	2004-08	15325984

Patents

Sample Use Guides

In Vivo Use Guide

10 mg or 20 mg indiplon capsules (4 weeks)

Route of Administration: Oral

In Vitro Use Guide

Indiplon inhibited the binding of [(3)H]Ro 15-1788 (flumazenil) to rat cerebellar and cerebral cortex membranes with high affinity (K(i) values of 0.55 and 0.45 nM, respectively).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:59 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:59 GMT 2025`
Record UNII	8BT63DA42E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALENTHYS

Preferred Name

English

INDIPLON

Official Name

English

CL-285489

Code

English

Indiplon [WHO-DD]

Common Name

English

INDIPLON [MI]

Common Name

English

INDIPLON [USAN]

Common Name

English

N-METHYL-N-(3-(3-(2-THIENYLCARBONYL)-PYRAZOLO(1,5-A)-PYRIMIDIN-7-YL)PHENYL)ACETAMIDE

Systematic Name

English

indiplon [INN]

Common Name

English

3-(2-THIENYLCARBONYL)-7-(3-N-METHYLACETAMIDE)-PYRAZOLO(1,5-.ALPHA.)PYRIMIDINE

Common Name

English

NBI-34060

Code

English

N-Methyl-N-[3-3-(thiophen-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]acetamide

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197