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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.

CNS Activity

Originator

American Cyanamid
37
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/16185169

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
 2.6 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
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:
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

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:
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
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
Neurocrine Biosciences, Inc. Soporific science.
2003 May
Gateways to clinical trials.
2003 Oct
Sleep and aging: prevalence of disturbed sleep and treatment considerations in older adults.
2005
Diagnosis and management of insomnia in older people.
2005 Jul
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
Gateways to clinical trials.
2006 Dec
Gateways to clinical trials.
2006 Jul-Aug
The new cancer fighter (and other hot drugs on the way).
2006 Mar 20
Relative abuse liability of indiplon and triazolam in humans: a comparison of psychomotor, subjective, and cognitive effects.
2007 Aug
Indiplon in the treatment of sleep disorders.
2007 Dec
Radiosynthesis and biological evaluation of an 18F-labeled derivative of the novel pyrazolopyrimidine sedative-hypnotic agent indiplon.
2007 Jul
Indiplon: the development of a novel therapy for the treatment of sleep onset and sleep maintenance insomnia.
2007 Jun
GABAA receptor pharmacology of fluorinated derivatives of the novel sedative-hypnotic pyrazolopyrimidine indiplon.
2008 Feb 2
Gateways to clinical trials.
2008 Sep
Patents

Patents

JP2006505569A
69
JP2007513956A
15
JP2007517040A
6

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 Fri Dec 15 15:54:45 UTC 2023
Edited
by admin
on Fri Dec 15 15:54:45 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL262075
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
PUBCHEM
6450813
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
MERCK INDEX
m6254
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID80186270
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
INN
8200
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
SMS_ID
300000034229
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
DRUG BANK
DB12590
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
FDA UNII
8BT63DA42E
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
CAS
325715-02-4
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
WIKIPEDIA
Indiplon
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
USAN
MM-52
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
NCI_THESAURUS
C74385
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
MESH
C469870
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
Related Record Type Details
GAMMA-AMINOBUTYRIC ACID RECEPTOR SUBUNIT ALPHA-1
TARGET->MODULATOR
Related Record Type Details
Structure of INDIPLON
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
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