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

Stem definition	Drug id	CAS RN
hypnotic tranquillizers	2873	43200-80-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: zopiclone zimovane imovane	S(+)-enantiomer of racemic zopiclone; azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; was term of zopiclone 2004-2007 Molecular weight: 388.81 Formula: C17H17ClN6O3 CLOGP: 1.25 LIPINSKI: 0 HAC: 9 HDO: 0 TPSA: 91.76 ALOGS: -2.64 ROTB: 3

Molecule

Description

Molfile Inchi Smiles

Synonyms:

zopiclone
zimovane
imovane

S(+)-enantiomer of racemic zopiclone; azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; was term of zopiclone 2004-2007

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

Drug dosage:

Dose	Unit	Route
7.50	mg	O

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	5.20 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	4.50 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	3.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	1.30 L/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.28 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
fu (Fraction unbound in plasma)	0.20 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.12 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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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
Lower respiratory tract infection	722.44	11.49	1035	113842	131272	63242873
Intentional overdose	697.36	11.49	762	114115	73390	63300755
Coma	595.70	11.49	656	114221	63708	63310437
Intentional self-injury	593.93	11.49	439	114438	25248	63348897
Folliculitis	457.21	11.49	599	114278	69718	63304427
Muscle injury	450.45	11.49	573	114304	64772	63309373
Muscle spasticity	445.29	11.49	346	114531	21448	63352697
Ill-defined disorder	431.81	11.49	630	114247	81125	63293020
Poisoning deliberate	410.88	11.49	255	114622	10963	63363182
Ear pain	403.28	11.49	407	114470	35711	63338434

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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
Depression	944.72	11.96	852	42323	96246	34817510
Drug interaction	661.28	11.96	1075	42100	224871	34688885
Poisoning deliberate	427.76	11.96	204	42971	7640	34906116
Coma	412.06	11.96	385	42790	45293	34868463
Loss of personal independence in daily activities	208.15	11.96	230	42945	32949	34880807
Intentional overdose	189.32	11.96	251	42924	43423	34870333
Psychiatric decompensation	186.80	11.96	85	43090	2852	34910904
Depression suicidal	154.61	11.96	71	43104	2434	34911322
Psychomotor skills impaired	149.56	11.96	80	43095	3826	34909930
Suicidal ideation	149.31	11.96	215	42960	40173	34873583

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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
Coma	934.82	10.45	1007	137295	99642	79506444
Poisoning deliberate	798.09	10.45	463	137839	18365	79587721
Intentional overdose	575.22	10.45	809	137493	105151	79500935
Intentional self-injury	363.13	10.45	359	137943	32060	79574026
Somnolence	361.79	10.45	1071	137231	237910	79368176
Lower respiratory tract infection	339.49	10.45	715	137587	128505	79477581
Depression	339.05	10.45	983	137319	215807	79390279
Ear pain	235.71	10.45	288	138014	32581	79573505
Muscle spasticity	226.11	10.45	230	138072	21245	79584841
Suicide attempt	208.59	10.45	451	137851	82481	79523605

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N05CF01	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 MODULATOR	Ki	6.75	WOMBAT-PK	DRUG LABEL
GABA-A receptor alpha-1/beta-2/gamma-2	Ion channel	P14867 P18507 P47870	GBRA1_HUMAN GBRG2_HUMAN GBRB2_HUMAN	POSITIVE MODULATOR	Ki	7.18	WOMBAT-PK	DRUG LABEL
GABA-A receptor alpha-5/beta-3/gamma-2	Ion channel	P18507 P28472 P31644	GBRG2_HUMAN GBRB3_HUMAN GBRA5_HUMAN	POSITIVE MODULATOR	Ki	7.28	WOMBAT-PK	DRUG LABEL
GABA-A receptor alpha-1/beta-2/gamma-3	Ion channel	P14867 P47870 Q99928	GBRA1_HUMAN GBRB2_HUMAN GBRG3_HUMAN	POSITIVE MODULATOR	Ki	7.16	WOMBAT-PK	DRUG LABEL
GABA A receptor alpha-3/beta-2/gamma-2	Ion channel	P18507 P34903 P47870	GBRG2_HUMAN GBRA3_HUMAN GBRB2_HUMAN	POSITIVE MODULATOR	Ki	6.58	WOMBAT-PK	DRUG LABEL
GABA A receptor alpha-3/beta-2/gamma-3	Ion channel	P34903 P47870 Q99928	GBRA3_HUMAN GBRB2_HUMAN GBRG3_HUMAN	POSITIVE MODULATOR	Ki	6.49	WOMBAT-PK	DRUG LABEL
GABA A receptor alpha-5/beta-3/gamma-3	Ion channel	P28472 P31644 Q99928	GBRB3_HUMAN GBRA5_HUMAN GBRG3_HUMAN	POSITIVE MODULATOR	Ki	6.75	WOMBAT-PK	DRUG LABEL
GABA A receptor alpha-5/beta-2/gamma-2	Ion channel	P18507 P31644 P47870	GBRG2_HUMAN GBRA5_HUMAN GBRB2_HUMAN	POSITIVE MODULATOR	Ki	7.28	WOMBAT-PK	DRUG LABEL
GABA-A receptor; anion channel	Ion channel		GBRP_RAT GBRB1_RAT GBRD_RAT GBRG2_RAT GBRA5_RAT GBRA3_RAT GBRG1_RAT GBRA2_RAT GBRA4_RAT GBRG3_RAT GBRA6_RAT GBRA1_RAT GBRB3_RAT GBRB2_RAT Q91ZM7_RAT GBRE_RAT		IC50	7.54	CHEMBL

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External reference:

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ID	Source
003775	NDDF
03A5ORL08Q	UNII
152527	RXNORM
321174005	SNOMEDCT_US
395929002	SNOMEDCT_US
4462	INN_ID
5735	PUBCHEM_CID
7430	IUPHAR_LIGAND_ID
C1436328	UMLSCUI
C515050	MESH_SUPPLEMENTAL_RECORD_UI

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Pharmaceutical products:

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