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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:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	5 %	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

Approvals:

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

FDA Adverse Event Reporting System (Female)

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
Somnambulism	45.71	12.51	24	15941	5519	63467538
Respiratory arrest	39.82	12.51	45	15920	32600	63440457
Drug intolerance	36.47	12.51	16	15949	308645	63164412
Treatment failure	36.01	12.51	4	15961	199039	63274018
Amnesia	35.76	12.51	56	15909	55529	63417528
Systemic lupus erythematosus	33.58	12.51	6	15959	208912	63264145
Suicide attempt	33.27	12.51	57	15908	60861	63412196
Maternal exposure during pregnancy	31.94	12.51	8	15957	220054	63253003
Paradoxical drug reaction	31.48	12.51	17	15948	4135	63468922
Joint swelling	31.46	12.51	22	15943	327644	63145413
Initial insomnia	30.20	12.51	19	15946	6138	63466919
Hand deformity	29.36	12.51	3	15962	159454	63313603
Abnormal dreams	27.27	12.51	22	15943	10494	63462563
Glossodynia	26.94	12.51	6	15959	178870	63294187
Cardio-respiratory arrest	26.27	12.51	51	15914	59908	63413149
Brain death	25.96	12.51	14	15951	3396	63469661
Abnormal sleep-related event	25.49	12.51	9	15956	784	63472273
Tremor	25.34	12.51	82	15883	132157	63340900
Cardiac arrest	25.09	12.51	65	15900	92480	63380577
Somnolence	25.03	12.51	100	15865	178585	63294472
Arthropathy	23.55	12.51	15	15950	234777	63238280
Hallucination	23.25	12.51	46	15919	54771	63418286
Alopecia	22.75	12.51	31	15934	337505	63135552
Concussion	21.18	12.51	18	15947	9226	63463831
Intentional overdose	21.05	12.51	53	15912	74099	63398958
Wound	20.01	12.51	8	15957	163255	63309802
Seizure	20.00	12.51	76	15889	132558	63340499
Toxicity to various agents	19.88	12.51	118	15847	247132	63225925
Hypersensitivity	19.59	12.51	27	15938	292658	63180399
Agitation	19.41	12.51	45	15920	59712	63413345
Infusion related reaction	19.25	12.51	20	15945	245501	63227556
Hangover	19.18	12.51	9	15956	1627	63471430
Blastocystis infection	18.98	12.51	4	15961	47	63473010
Unresponsive to stimuli	18.93	12.51	32	15933	33784	63439273
Electrocardiogram QRS complex prolonged	18.83	12.51	14	15951	5924	63467133
Fall	18.14	12.51	164	15801	392170	63080887
Product substitution issue	17.74	12.51	21	15944	15975	63457082
Hallucination, visual	17.65	12.51	23	15942	19275	63453782
General physical health deterioration	17.43	12.51	15	15950	201387	63271670
Areflexia	16.25	12.51	10	15955	3108	63469949
Migraine	16.23	12.51	60	15905	103286	63369771
Restlessness	15.34	12.51	27	15938	29426	63443631
Feeling abnormal	14.72	12.51	75	15890	148317	63324740
Ventricular tachyarrhythmia	14.67	12.51	4	15961	147	63472910
Helicobacter infection	14.19	12.51	3	15962	92782	63380275
Irritability	13.93	12.51	27	15938	31667	63441390
Off label use	13.91	12.51	106	15859	674356	62798701
Carbon monoxide poisoning	13.62	12.51	4	15961	193	63472864
Malignant catatonia	13.56	12.51	4	15961	196	63472861
Drug interaction	13.53	12.51	23	15942	229108	63243949
Respiratory acidosis	13.22	12.51	12	15953	6703	63466354
Product use issue	13.15	12.51	22	15943	220498	63252559
Anterograde amnesia	13.10	12.51	5	15960	542	63472515
Rheumatoid arthritis	12.80	12.51	28	15937	253791	63219266
Abdominal discomfort	12.67	12.51	40	15925	320845	63152212
Palpitations	12.61	12.51	59	15906	112711	63360346
Swelling	12.59	12.51	32	15933	275346	63197711

FDA Adverse Event Reporting System (Male)

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
Suicidal ideation	33.19	14.60	44	8138	40344	34908405
Somnolence	29.53	14.60	74	8108	111042	34837707
Nightmare	28.51	14.60	25	8157	14366	34934383
Somnambulism	28.30	14.60	14	8168	3058	34945691
Anxiety	22.12	14.60	62	8120	99366	34849383
Intentional overdose	19.59	14.60	36	8146	43638	34905111
Abnormal dreams	18.81	14.60	15	8167	7563	34941186
Gun shot wound	16.21	14.60	7	8175	1121	34947628
Amnesia	14.65	14.60	24	8158	26539	34922210

FDA Adverse Event Reporting System (Geriatric)

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
Nightmare	44.84	12.74	41	17934	25820	79700593
Altered state of consciousness	44.30	12.74	52	17923	43770	79682643
Suicidal ideation	44.11	12.74	69	17906	76271	79650142
Anxiety	41.72	12.74	137	17838	248375	79478038
Depression	41.43	12.74	125	17850	216665	79509748
Somnolence	36.81	12.74	128	17847	238853	79487560
Amnesia	35.05	12.74	56	17919	63001	79663412
Intentional overdose	30.30	12.74	71	17904	105889	79620524
Abnormal dreams	29.97	12.74	23	17952	11389	79715024
Cardio-respiratory arrest	29.18	12.74	71	17904	108439	79617974
Cardiac arrest	28.08	12.74	94	17881	172002	79554411
Hepatic function abnormal	27.81	12.74	55	17920	73052	79653361
Paradoxical drug reaction	26.98	12.74	18	17957	7167	79719246
Drug intolerance	23.91	12.74	15	17960	264104	79462309
Anterograde amnesia	23.67	12.74	8	17967	683	79725730
Treatment failure	23.26	12.74	5	17970	170481	79555932
Brain death	23.21	12.74	15	17960	5662	79720751
Contraindicated product administered	22.80	12.74	4	17971	157534	79568879
Off label use	21.82	12.74	118	17857	907097	78819316
Joint swelling	21.53	12.74	20	17955	288626	79437787
Pneumonia aspiration	21.51	12.74	47	17928	66920	79659493
Interstitial lung disease	20.62	12.74	64	17911	112536	79613877
General physical health deterioration	20.61	12.74	19	17956	275219	79451194
Drug interaction	20.53	12.74	39	17936	415144	79311269
Acute kidney injury	19.88	12.74	56	17919	519348	79207065
Blastocystis infection	19.34	12.74	4	17971	48	79726365
Hallucination	18.82	12.74	52	17923	85693	79640720
Toxicity to various agents	18.51	12.74	160	17815	421380	79305033
Delirium	18.26	12.74	51	17924	84576	79641837
Abnormal sleep-related event	18.08	12.74	7	17968	882	79725531
Hangover	17.93	12.74	9	17966	2103	79724310
Restlessness	17.70	12.74	35	17940	46457	79679956
Drug ineffective	17.21	12.74	340	17635	1080573	78645840
Infusion related reaction	17.11	12.74	16	17959	230221	79496192
Fall	16.42	12.74	175	17800	487454	79238959
Poisoning	16.22	12.74	24	17951	25248	79701165
Gun shot wound	16.22	12.74	7	17968	1163	79725250
Systemic lupus erythematosus	15.64	12.74	4	17971	121145	79605268
Thrombocytopenia	14.86	12.74	23	17952	265236	79461177
Electrocardiogram QRS complex prolonged	14.68	12.74	15	17960	10818	79715595
Hand deformity	14.27	12.74	3	17972	103916	79622497
Areflexia	14.20	12.74	11	17964	5523	79720890
Hallucination, visual	14.14	12.74	26	17949	32703	79693710
Product use in unapproved indication	13.74	12.74	22	17953	250337	79476076
Arthropathy	13.52	12.74	12	17963	177099	79549314
Maternal exposure during pregnancy	13.43	12.74	7	17968	136531	79589882
Sleep talking	13.39	12.74	6	17969	1090	79725323
Irritability	13.35	12.74	29	17946	41115	79685298
Road traffic accident	13.29	12.74	30	17945	43634	79682779

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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

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

🐶 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:

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

External reference:

ID	Source
4024906	VUID
N0000175354	NUI
D02624	KEGG_DRUG
4024906	VANDF
C1436328	UMLSCUI
CHEBI:53760	CHEBI
ZPC	PDB_CHEM_ID
CHEMBL1522	ChEMBL_ID
DB00402	DRUGBANK_ID
D000069582	MESH_DESCRIPTOR_UI
887	PUBCHEM_CID
7429	IUPHAR_LIGAND_ID
8258	INN_ID
UZX80K71OE	UNII
461016	RXNORM
19107	MMSL
216714	MMSL
64025	MMSL
d05421	MMSL
008781	NDDF
409420000	SNOMEDCT_US
409421001	SNOMEDCT_US

Pharmaceutical products:

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
Lunesta	HUMAN PRESCRIPTION DRUG LABEL	1	21695-225	TABLET, COATED	2 mg	ORAL	NDA	30 sections
Lunesta	HUMAN PRESCRIPTION DRUG LABEL	1	21695-226	TABLET, COATED	3 mg	ORAL	NDA	30 sections
Eszopiclone	Human Prescription Drug Label	1	33342-299	TABLET, FILM COATED	1 mg	ORAL	ANDA	31 sections
Eszopiclone	Human Prescription Drug Label	1	33342-299	TABLET, FILM COATED	1 mg	ORAL	ANDA	31 sections
Eszopiclone	Human Prescription Drug Label	1	33342-300	TABLET, FILM COATED	2 mg	ORAL	ANDA	31 sections
Eszopiclone	Human Prescription Drug Label	1	33342-300	TABLET, FILM COATED	2 mg	ORAL	ANDA	31 sections
Eszopiclone	Human Prescription Drug Label	1	33342-301	TABLET, FILM COATED	3 mg	ORAL	ANDA	31 sections
Eszopiclone	Human Prescription Drug Label	1	33342-301	TABLET, FILM COATED	3 mg	ORAL	ANDA	31 sections
ESZOPICLONE	HUMAN PRESCRIPTION DRUG LABEL	1	42043-320	TABLET, FILM COATED	1 mg	ORAL	ANDA	29 sections
ESZOPICLONE	HUMAN PRESCRIPTION DRUG LABEL	1	42043-321	TABLET, FILM COATED	2 mg	ORAL	ANDA	29 sections
ESZOPICLONE	HUMAN PRESCRIPTION DRUG LABEL	1	42043-322	TABLET, FILM COATED	3 mg	ORAL	ANDA	29 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43063-795	TABLET, FILM COATED	3 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43063-795	TABLET, FILM COATED	3 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43063-795	TABLET, FILM COATED	3 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43353-097	TABLET, FILM COATED	3 mg	ORAL	ANDA	31 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43353-101	TABLET, FILM COATED	2 mg	ORAL	ANDA	31 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43353-185	TABLET, FILM COATED	3 mg	ORAL	ANDA	32 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	43353-200	TABLET, FILM COATED	2 mg	ORAL	ANDA	32 sections
ESZOPICLONE	HUMAN PRESCRIPTION DRUG LABEL	1	45865-828	TABLET, FILM COATED	3 mg	ORAL	ANDA	30 sections
ESZOPICLONE	HUMAN PRESCRIPTION DRUG LABEL	1	45865-829	TABLET, FILM COATED	2 mg	ORAL	ANDA	30 sections
ESZOPICLONE	HUMAN PRESCRIPTION DRUG LABEL	1	45865-830	TABLET, FILM COATED	1 mg	ORAL	ANDA	30 sections