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Details

Stereochemistry ACHIRAL
Molecular Formula C20H15FN4O2S
Molecular Weight 394.422
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOREDIPLON

SMILES

CN(C(C)=O)C1=C(F)C=CC(=C1)C2=CC=NC3=C(C=NN23)C(=O)C4=CC=CS4

InChI

InChIKey=NQPOCLFSADOXBR-UHFFFAOYSA-N
InChI=1S/C20H15FN4O2S/c1-12(26)24(2)17-10-13(5-6-15(17)21)16-7-8-22-20-14(11-23-25(16)20)19(27)18-4-3-9-28-18/h3-11H,1-2H3

HIDE SMILES / InChI

Molecular Formula C20H15FN4O2S
Molecular Weight 394.422
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://link.springer.com/chapter/10.1007%2F978-3-319-11514-6_6 | https://www.ncbi.nlm.nih.gov/pubmed/25423562

Lorediplon is a novel non-benzodiazepine, the hypnotic drug acting as a GABAA receptor modulator, differentially active at the alpha1-subunit, associated with promoting sleep. As compared with other selective benzodiazepine receptor agonists, lorediplon has demonstrated in pre-clinical studies a potent hypnotic profile with potential advantages in sleep maintenance and sleep architecture preservation associated with a good safety profile, that is, no induction of tolerance, lack of next-day hangover effect, weak effect on muscular tone, and weak interaction with ethanol. Lorediplon demonstrated a minimum of 10-fold and the 6-fold increase in potency (respectively) in the spontaneous motor activation studies, compared with the currently marketed hypnotics (zolpidem and zaleplon). Additionally, when the electroencephalogram (EEG) effects of lorediplon and zolpidem were compared in the sleep-wake cycle in the mouse, lorediplon demonstrated a 10-fold increase in potency compared with zolpidem in the sleep-wake cycle and 13% greater possibility of fewer wake episodes than zolpidem. At concentrations of 1.2mg/kg, lorediplon demonstrated a 57%increased effect on Slow Wave Sleep (SWS), when compared with a placebo. In clinical trials, the clinical safety and tolerability were excellent for all doses tested. In pharmacokinetic studies, after oral administration, lorediplon is rapidly absorbed from the gastrointestinal tract reaching maximum plasma concentrations at approximately 2 h. Lorediplon demonstrated a dose-dependent improvement in sleep, whereas zolpidem showed a more sustained wake after sleep onset effect. No next-day hangover effects were observed. These sleep effects are also consistent with the pharmacokinetic profile of lorediplon.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A single-dose, randomized, double-blind, double dummy, placebo and positive-controlled, five-way cross-over study to assess the pharmacodynamic effects of lorediplon in a phase advance model of insomnia in healthy Caucasian adult male subjects.
2014 May
Patents

Sample Use Guides

single-dose administration of lorediplon 1, 5, or 10 mg
Route of Administration: Oral
The in vitro potency as well as the efficacy of Lorediplon was studied in an assay measuring the function of the most common GABAA receptor subtypes (namely, α1β2γ2, α2β2/3γ2, α3β2/3γ2, α5β2γ2) expressed in Xenopus laevis. The results showed that Lorediplon is a potent positive allosteric modulator of Cl_ currents mediated by the GABAA sub-receptors studied and a fourfold potency selectivity for α1β2γ2 receptors over other subtypes was observed
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:39:36 GMT 2023
Edited
by admin
on Fri Dec 15 20:39:36 GMT 2023
Record UNII
VKU6Z23NSY
Record Status Validated (UNII)
Record Version
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Name Type Language
LOREDIPLON
INN   WHO-DD  
INN  
Official Name English
lorediplon [INN]
Common Name English
Lorediplon [WHO-DD]
Common Name English
N-(2-FLUORO-5-(3-(THIOPHENE-2-CARBONYL)PYRAZOLO(1,5-A)PYRIMIDIN-7-YL)PHENYL)-N-METHYLACETAMIDE
Systematic Name English
ACETAMIDE, N-(2-FLUORO-5-(3-(2-THIENYLCARBONYL)PYRAZOLO(1,5-A)PYRIMIDIN-7-YL)PHENYL)-N-METHYL-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
LOREDIPLON
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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FDA UNII
VKU6Z23NSY
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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NCI_THESAURUS
C170129
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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PUBCHEM
12004146
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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SMS_ID
300000037019
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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EPA CompTox
DTXSID00238684
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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CAS
917393-39-6
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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ChEMBL
CHEMBL3707317
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
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INN
9348
Created by admin on Fri Dec 15 20:39:36 GMT 2023 , Edited by admin on Fri Dec 15 20:39:36 GMT 2023
PRIMARY
Related Record Type Details
TARGET->MODULATOR
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ACTIVE MOIETY