INDIPLON

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

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 179		2.6 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16185169 https://www.ncbi.nlm.nih.gov/pubmed/18246982	Primary		Phase III 656	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral (unknown) 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 n = 91 Health Status: unhealthy Condition: insomnia Sex: M+F Food Status: UNKNOWN Population Size: 91 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 (unknown) 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 n = 91 Health Status: unhealthy Condition: insomnia Sex: M+F Food Status: UNKNOWN Population Size: 91 Sources: https://pubmed.ncbi.nlm.nih.gov/18246982
Somnolence	7.8%	20 mg 1 times / day multiple, oral (unknown) 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 n = 91 Health Status: unhealthy Condition: insomnia Sex: M+F Food Status: UNKNOWN Population Size: 91 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
Hairui	HR148973	http://www.hairuichem.com/en/product/search.do?q=HR148973
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
eMolecules	10705189	https://orderbb.emolecules.com/search/#?query=10705189
mcule	MCULE-5857056440	https://mcule.com/MCULE-5857056440/

PubMed

Title	Date	PubMed
		252159878
Indiplon. Indiplon modified-release, indiplon MR, NBI 34060, NBI 34060 modified-release, NBI 34060 MR.	2002	12099167
Gateways to clinical trials.	2004 Jul-Aug	15349141
In vivo pharmacological characterization of indiplon, a novel pyrazolopyrimidine sedative-hypnotic.	2004 Nov	15256538
Gateways to clinical trials.	2004 Oct	15605126
Sleep and aging: prevalence of disturbed sleep and treatment considerations in older adults.	2005	16336039
Gateways to clinical trials.	2005 Apr	15834452
Gateways to clinical trials.	2006 Oct	17136234
Gateways to clinical trials.	2006 Sep	17003851
Relative abuse liability of indiplon and triazolam in humans: a comparison of psychomotor, subjective, and cognitive effects.	2007 Aug	17502431
Efficacy and safety of as-needed, post bedtime dosing with indiplon in insomnia patients with chronic difficulty maintaining sleep.	2007 Dec	18246982
Auto-modulation of neuroactive steroids on GABA A receptors: a novel pharmacological effect.	2007 Feb	17084864
In vitro metabolism of indiplon and an assessment of its drug interaction potential.	2007 Jul	17620220
Radiosynthesis and biological evaluation of an 18F-labeled derivative of the novel pyrazolopyrimidine sedative-hypnotic agent indiplon.	2007 Jul	17591556
[New hypnotics: perspectives from sleep physiology].	2007 Jul-Aug	18265473
Efficacy and tolerability of indiplon in transient insomnia.	2007 Jun 15	17694726
Gaboxadol, a selective extrasynaptic GABA(A) agonist, does not generalise to other sleep-enhancing drugs: a rat drug discrimination study.	2007 Mar	17196996
Indiplon: a nonbenzodiazepine sedative-hypnotic for the treatment of insomnia.	2008 Jul	18594049
Gaboxadol -- a different hypnotic profile with no tolerance to sleep EEG and sedative effects after repeated daily dosing.	2008 Jul	18304623
Post-bedtime dosing with indiplon in adults and the elderly: results from two placebo-controlled, active comparator crossover studies in healthy volunteers.	2008 Mar	18257978
Gateways to clinical trials.	2008 Sep	18985183

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).

Name

Type

Language

INDIPLON

Official Name

English

CL-285489

Code

English

Indiplon [WHO-DD]

Common Name

English

INDIPLON [MI]

Common Name

English

CALENTHYS

Brand 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