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eszopiclone 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:

None

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	669.24	12.85	295	13315	40196	46632256
Insomnia	310.87	12.85	306	13304	164618	46507834
Completed suicide	146.84	12.85	196	13414	145724	46526728
Middle insomnia	94.56	12.85	49	13561	9466	46662986
Parasomnia	72.18	12.85	18	13592	397	46672055
Depression	55.19	12.85	140	13470	169964	46502488
Suicidal ideation	50.91	12.85	72	13538	56310	46616142
Anxiety	48.22	12.85	139	13471	181818	46490634
Nightmare	47.27	12.85	39	13571	16559	46655893
Somnambulism	41.77	12.85	23	13587	5014	46667438
Paradoxical drug reaction	38.11	12.85	17	13593	2359	46670093
Amnesia	37.32	12.85	53	13557	41578	46630874
Initial insomnia	33.30	12.85	19	13591	4433	46668019
Overdose	29.01	12.85	80	13530	101899	46570553
Suicide attempt	28.86	12.85	55	13555	54981	46617471
Respiratory arrest	28.77	12.85	42	13568	33774	46638678
Abnormal sleep-related event	28.49	12.85	10	13600	737	46671715
Abnormal dreams	24.87	12.85	22	13588	10257	46662195
Drug ineffective	21.99	12.85	297	13313	677541	45994911
Blastocystis infection	21.94	12.85	4	13606	17	46672435
Concussion	21.08	12.85	17	13593	6986	46665466
Somnolence	20.39	12.85	95	13515	156426	46516026
Drug interaction	18.67	12.85	19	13591	203075	46469377
Cardiac arrest	17.44	12.85	62	13548	90337	46582115
Rheumatoid arthritis	17.36	12.85	27	13583	240188	46432264
Hangover	16.81	12.85	8	13602	1287	46671165
Ventricular tachyarrhythmia	16.41	12.85	4	13606	80	46672372
Cardio-respiratory arrest	16.06	12.85	46	13564	59823	46612629
Drug intolerance	15.62	12.85	12	13598	147037	46525415
Treatment failure	15.50	12.85	4	13606	93083	46579369
Agitation	15.28	12.85	43	13567	55372	46617080
Hallucination	15.01	12.85	40	13570	49911	46622541
Tremor	14.91	12.85	70	13540	115569	46556883
Maternal exposure during pregnancy	14.28	12.85	6	13604	102543	46569909
Acute kidney injury	13.93	12.85	30	13580	235825	46436627
Electrocardiogram QRS complex prolonged	13.86	12.85	12	13598	5437	46667015
Intentional overdose	13.80	12.85	46	13564	64898	46607554
Product substitution issue	13.26	12.85	19	13591	15012	46657440

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	292.67	14.57	134	6929	24667	29920748
Insomnia	190.86	14.57	165	6898	93171	29852244
Completed suicide	149.17	14.57	148	6915	99344	29846071
Parasomnia	82.16	14.57	18	7045	276	29945139
Middle insomnia	70.46	14.57	32	7031	5741	29939674
Initial insomnia	68.46	14.57	25	7038	2564	29942851
Suicide attempt	63.09	14.57	59	7004	36638	29908777
Drug ineffective	61.13	14.57	197	6866	340190	29605225
Altered state of consciousness	34.15	14.57	32	7031	19887	29925528
Suicidal ideation	32.03	14.57	41	7022	36073	29909342
Somnolence	29.22	14.57	68	6995	96695	29848720
Nightmare	27.92	14.57	23	7040	12053	29933362
Somnambulism	27.60	14.57	14	7049	3200	29942215
Overdose	24.07	14.57	58	7005	84279	29861136
Anxiety	19.70	14.57	56	7007	89815	29855600
Abnormal dreams	17.81	14.57	15	7048	8100	29937315
Gun shot wound	15.76	14.57	7	7056	1191	29944224
Intentional overdose	15.74	14.57	32	7031	41449	29903966

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	cns depressants
CHEBI has role	CHEBI:35717	sedatives

Drug Use (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

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-1/beta-2/gamma-2	Ion channel	P14867 P18507 P47870	GBRA1_HUMAN GBRB2_HUMAN GBRG2_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
GABA A receptor alpha-3/beta-2/gamma-2	Ion channel	P18507 P34903 P47870	GBRA3_HUMAN GBRB2_HUMAN GBRG2_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	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-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-5/beta-2/gamma-2	Ion channel	P18507 P31644 P47870	GBRA5_HUMAN GBRB2_HUMAN GBRG2_HUMAN	POSITIVE ALLOSTERIC MODULATOR			WOMBAT-PK	CHEMBL
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-4	Ion channel	P48169	GBRA4_HUMAN	POSITIVE ALLOSTERIC MODULATOR	Ki	6.99	CHEMBL	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-2	Ion channel	P47869	GBRA2_HUMAN	POSITIVE ALLOSTERIC MODULATOR	Ki	6.94	CHEMBL	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-1	Ion channel	P14867	GBRA1_HUMAN		Ki	7.30	CHEMBL
Gamma-aminobutyric acid receptor subunit alpha-3	Ion channel	P34903	GBRA3_HUMAN		Ki	6.79	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
969472	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	31 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5538	TABLET, FILM COATED	2 mg	ORAL	ANDA	31 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5539	TABLET, FILM COATED	3 mg	ORAL	ANDA	31 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	0378-5272	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	33342-300	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	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	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
ESZOPICLONE	Human Prescription Drug Label	1	47335-586	TABLET, FILM COATED	1 mg	ORAL	ANDA	30 sections
ESZOPICLONE	Human Prescription Drug Label	1	47335-587	TABLET, FILM COATED	2 mg	ORAL	ANDA	30 sections
ESZOPICLONE	Human Prescription Drug Label	1	47335-588	TABLET, FILM COATED	3 mg	ORAL	ANDA	30 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2606	TABLET, FILM COATED	1 mg	ORAL	ANDA	31 sections
ESZOPICLONE	Human Prescription Drug Label	1	50090-3514	TABLET, FILM COATED	3 mg	ORAL	ANDA	31 sections
ESZOPICLONE	Human Prescription Drug Label	1	50090-3553	TABLET, FILM COATED	1 mg	ORAL	ANDA	31 sections
Eszopiclone	HUMAN PRESCRIPTION DRUG LABEL	1	50090-3989	TABLET, FILM COATED	1 mg	ORAL	ANDA	30 sections
ESZOPICLONE	Human Prescription Drug Label	1	50090-4202	TABLET, FILM COATED	2 mg	ORAL	ANDA	31 sections