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eszopiclone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
hypnotic tranquillizers	1068	138729-47-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: eszopiclone esopiclone lunesta	A pyridine, pyrazine, and piperazine derivative that is used as a HYPNOTIC AND SEDATIVE in the treatment of INSOMNIA. Molecular weight: 388.81 Formula: C17H17ClN6O3 CLOGP: 1.25 LIPINSKI: 0 HAC: 9 HDO: 0 TPSA: 91.76 ALOGS: -2.64 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

eszopiclone
esopiclone
lunesta

A pyridine, pyrazine, and piperazine derivative that is used as a HYPNOTIC AND SEDATIVE in the treatment of INSOMNIA.

Molecular weight: 388.81
Formula: C17H17ClN6O3
CLOGP: 1.25
LIPINSKI: 0
HAC: 9
HDO: 0
TPSA: 91.76
ALOGS: -2.64
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
2	mg	O

ADMET properties:

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	5 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.11 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

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Approvals:

Date	Agency	Company	Orphan
Dec. 15, 2004	FDA	SUNOVION PHARMS INC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Dysgeusia	679.94	12.51	298	15667	46412	63426645
Completed suicide	226.67	12.51	228	15737	145445	63327612
Insomnia	117.51	12.51	201	15764	215051	63258006
Middle insomnia	88.27	12.51	49	15916	12594	63460463
Parasomnia	69.98	12.51	18	15947	526	63472531
Depression	68.55	12.51	152	15813	196340	63276717
Suicidal ideation	61.27	12.51	77	15888	62344	63410713
Anxiety	60.41	12.51	154	15811	217387	63255670
Overdose	56.88	12.51	103	15862	114975	63358082
Nightmare	47.35	12.51	39	15926	19155	63453902

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Dysgeusia	284.99	14.60	134	8048	26363	34922386
Completed suicide	182.52	14.60	164	8018	98004	34850745
Parasomnia	76.59	14.60	18	8164	386	34948363
Suicide attempt	69.79	14.60	64	8118	39052	34909697
Insomnia	68.92	14.60	102	8080	103805	34844944
Middle insomnia	65.67	14.60	32	8150	6770	34941979
Initial insomnia	60.55	14.60	24	8158	3100	34945649
Drug ineffective	41.44	14.60	213	7969	456538	34492211
Altered state of consciousness	37.99	14.60	36	8146	22857	34925892
Overdose	33.51	14.60	69	8113	90990	34857759

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Dysgeusia	541.78	12.74	262	17713	56915	79669498
Completed suicide	425.73	12.74	388	17587	245379	79481034
Parasomnia	123.35	12.74	28	17947	533	79725880
Middle insomnia	103.79	12.74	57	17918	16012	79710401
Insomnia	93.05	12.74	184	17791	244986	79481427
Suicide attempt	83.23	12.74	98	17877	82834	79643579
Initial insomnia	75.38	12.74	35	17940	6903	79719510
Overdose	63.59	12.74	133	17842	184073	79542340
Somnambulism	56.43	12.74	27	17948	5694	79720719
Respiratory arrest	56.06	12.74	67	17908	57483	79668930

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N05CF04	NERVOUS SYSTEM PSYCHOLEPTICS HYPNOTICS AND SEDATIVES Benzodiazepine related drugs
CHEBI has role	CHEBI:35488	central nervous system depressants
CHEBI has role	CHEBI:35717	hypnotics
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D006993	Hypnotics and Sedatives

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID
Insomnia	indication	193462001
Suicidal thoughts	contraindication	6471006
Asthenia	contraindication	13791008
Alcohol intoxication	contraindication	25702006
Depressive disorder	contraindication	35489007
Hepatic failure	contraindication	59927004
Sleep automatism	contraindication	247962006
Severe chronic obstructive pulmonary disease	contraindication	313299006

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.95	Basic
pKa2	2.26	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
GABA A receptor alpha-5/beta-2/gamma-3	Ion channel	P31644 P47870 Q99928	GBRA5_HUMAN GBRB2_HUMAN GBRG3_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-2	Ion channel	P47869	GBRA2_HUMAN	POSITIVE ALLOSTERIC MODULATOR	Ki	6.94	CHEMBL	CHEMBL
GABA A receptor alpha-3/beta-2/gamma-3	Ion channel	P34903 P47870 Q99928	GBRA3_HUMAN GBRB2_HUMAN GBRG3_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
GABA A receptor alpha-5/beta-2/gamma-2	Ion channel	P18507 P31644 P47870	GBRG2_HUMAN GBRA5_HUMAN GBRB2_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-4	Ion channel	P48169	GBRA4_HUMAN	POSITIVE ALLOSTERIC MODULATOR	Ki	6.99	CHEMBL	CHEMBL
GABA-A receptor alpha-1/beta-2/gamma-2	Ion channel	P14867 P18507 P47870	GBRA1_HUMAN GBRG2_HUMAN GBRB2_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
GABA-A receptor alpha-1/beta-2/gamma-3	Ion channel	P14867 P47870 Q99928	GBRA1_HUMAN GBRB2_HUMAN GBRG3_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
GABA A receptor alpha-3/beta-2/gamma-2	Ion channel	P18507 P34903 P47870	GBRG2_HUMAN GBRA3_HUMAN GBRB2_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-3	Ion channel	P34903	GBRA3_HUMAN		Ki	6.79	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-1	Ion channel	P14867	GBRA1_HUMAN		Ki	7.30	CHEMBL

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External reference:

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ID	Source
008781	NDDF
19107	MMSL
216714	MMSL
4024906	VUID
4024906	VANDF
409420000	SNOMEDCT_US
409421001	SNOMEDCT_US
461016	RXNORM
64025	MMSL
7429	IUPHAR_LIGAND_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5537	TABLET, FILM COATED	1 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5538	TABLET, FILM COATED	2 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5539	TABLET, FILM COATED	3 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5270	TABLET, FILM COATED	1 mg	ORAL	ANDA	32 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5270	TABLET, FILM COATED	1 mg	ORAL	ANDA	32 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5271	TABLET, FILM COATED	2 mg	ORAL	ANDA	32 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5271	TABLET, FILM COATED	2 mg	ORAL	ANDA	32 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5272	TABLET, FILM COATED	3 mg	ORAL	ANDA	32 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5272	TABLET, FILM COATED	3 mg	ORAL	ANDA	32 sections
Eszopiclone	Human Prescription Drug Label	1	33342-299	TABLET, FILM COATED	1 mg	ORAL	ANDA	31 sections

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