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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 of INDIPLON

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
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.

Originator

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/16185169

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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:
unhealthy
n = 91
Health Status: unhealthy
Condition: insomnia
Sex: M+F
Food Status: UNKNOWN
Population Size: 91
Sources:
Other AEs: Somnolence, Headache...
Other AEs:
Somnolence (7.8%)
Headache (6.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
n = 91
Health Status: unhealthy
Condition: insomnia
Sex: M+F
Food Status: UNKNOWN
Population Size: 91
Sources:
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:
unhealthy
n = 91
Health Status: unhealthy
Condition: insomnia
Sex: M+F
Food Status: UNKNOWN
Population Size: 91
Sources:
PubMed

PubMed

TitleDatePubMed
Indiplon. Indiplon modified-release, indiplon MR, NBI 34060, NBI 34060 modified-release, NBI 34060 MR.
2002
Gateways to clinical trials.
2004 Dec
Gateways to clinical trials.
2004 Jul-Aug
Characterization of the interaction of indiplon, a novel pyrazolopyrimidine sedative-hypnotic, with the GABAA receptor.
2004 Nov
Gateways to clinical trials.
2004 Oct
Sleep and aging: prevalence of disturbed sleep and treatment considerations in older adults.
2005
Gateways to clinical trials.
2005 Apr
Diagnosis and management of insomnia in older people.
2005 Jul
Gateways to clinical trials.
2005 Jul-Aug
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 Nov
Indiplon: the development of a new hypnotic.
2005 Oct
Gateways to clinical trials.
2005 Sep
Indiplon is a high-affinity positive allosteric modulator with selectivity for alpha1 subunit-containing GABAA receptors.
2006 Apr
Insomnia in the elderly: cause, approach, and treatment.
2006 Jun
Gateways to clinical trials.
2006 Sep
Indiplon in the treatment of sleep disorders.
2007 Dec
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
Efficacy and tolerability of indiplon in transient insomnia.
2007 Jun 15
Efficacy and tolerability of indiplon in older adults with primary insomnia.
2007 Nov
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
Gaboxadol -- a different hypnotic profile with no tolerance to sleep EEG and sedative effects after repeated daily dosing.
2008 Jul
Post-bedtime dosing with indiplon in adults and the elderly: results from two placebo-controlled, active comparator crossover studies in healthy volunteers.
2008 Mar
Discriminative stimulus effects of tiagabine and related GABAergic drugs in rats.
2008 May
Gateways to clinical trials.
2008 Sep
Indiplon in the management of insomnia.
2009 Sep 21
[The newer sedative-hypnotics].
2010 Sep
Patents

Sample Use Guides

10 mg or 20 mg indiplon capsules (4 weeks)
Route of Administration: Oral
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 Fri Dec 15 15:54:45 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:45 GMT 2023
Record UNII
8BT63DA42E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDIPLON
DASH   INN   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL262075
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
PUBCHEM
6450813
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
MERCK INDEX
m6254
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID80186270
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
INN
8200
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
SMS_ID
300000034229
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
DRUG BANK
DB12590
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
FDA UNII
8BT63DA42E
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
CAS
325715-02-4
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
WIKIPEDIA
Indiplon
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
USAN
MM-52
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
NCI_THESAURUS
C74385
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
MESH
C469870
Created by admin on Fri Dec 15 15:54:45 GMT 2023 , Edited by admin on Fri Dec 15 15:54:45 GMT 2023
PRIMARY
Related Record Type Details
TARGET->MODULATOR
Related Record Type Details
ACTIVE MOIETY