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flunitrazepam Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
diazepam derivatives	1202	1622-62-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: flunitrazepam flunidazepam fluridrazepam flunipam	A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug. Molecular weight: 313.29 Formula: C16H12FN3O3 CLOGP: 1.78 LIPINSKI: 0 HAC: 6 HDO: 0 TPSA: 78.49 ALOGS: -4.56 ROTB: 2

Molecule

Description

Molfile Inchi Smiles

Synonyms:

flunitrazepam
flunidazepam
fluridrazepam
flunipam

A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.

Molecular weight: 313.29
Formula: C16H12FN3O3
CLOGP: 1.78
LIPINSKI: 0
HAC: 6
HDO: 0
TPSA: 78.49
ALOGS: -4.56
ROTB: 2

Drug dosage:

Dose	Unit	Route
1	mg	O
1	mg	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.00 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	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
BA (Bioavailability)	80 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	1.90 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.40 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.17 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	25 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 1, 1976	YEAR INTRODUCED

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
Intentional overdose	136.60	24.75	83	4526	64861	46616592
Suicide attempt	130.48	24.75	76	4533	54960	46626493
Neuroleptic malignant syndrome	127.13	24.75	46	4563	11076	46670377
Altered state of consciousness	125.28	24.75	56	4553	23292	46658161
Overdose	122.35	24.75	92	4517	101887	46579566
Psychiatric symptom	80.34	24.75	26	4583	4471	46676982
Salivary hypersecretion	60.21	24.75	23	4586	6422	46675031
Hepatic function abnormal	59.71	24.75	39	4570	34382	46647071
Blood creatine phosphokinase increased	59.62	24.75	36	4573	27688	46653765
Extrapyramidal disorder	57.12	24.75	26	4583	11242	46670211
Parkinsonism	55.53	24.75	23	4586	7925	46673528
Delusion	51.05	24.75	24	4585	11164	46670289
Stevens-Johnson syndrome	49.43	24.75	30	4579	23267	46658186
Pneumonia aspiration	48.05	24.75	33	4576	31572	46649881
Carcinoid tumour of the stomach	47.75	24.75	9	4600	158	46681295
Hypothermia	46.13	24.75	23	4586	12160	46669293
Hypergastrinaemia	44.62	24.75	8	4601	105	46681348
Depressed level of consciousness	44.18	24.75	37	4572	47532	46633921
Toxicity to various agents	43.33	24.75	76	4533	211690	46469763
Rhabdomyolysis	41.85	24.75	34	4575	41875	46639578
Enterochromaffin cell hyperplasia	41.66	24.75	7	4602	61	46681392
White blood cell count increased	40.25	24.75	34	4575	44185	46637268
Electrocardiogram QT prolonged	39.76	24.75	36	4573	51289	46630164
Loss of consciousness	36.47	24.75	49	4560	108189	46573264
Lip erosion	33.72	24.75	9	4600	790	46680663
Drowning	33.62	24.75	8	4601	441	46681012
Water intoxication	33.41	24.75	8	4601	453	46681000
Neuroendocrine tumour	31.38	24.75	8	4601	587	46680866
Peritoneal perforation	30.90	24.75	6	4603	124	46681329
Pyrexia	30.27	24.75	89	4520	348713	46332740
Liver disorder	28.59	24.75	26	4583	37220	46644233
Electrocardiogram J wave abnormal	28.18	24.75	4	4605	9	46681444
Sudden death	27.54	24.75	15	4594	9489	46671964
Aspiration	27.50	24.75	15	4594	9516	46671937
Brain injury	27.46	24.75	13	4596	6137	46675316
Schizophrenia	26.16	24.75	14	4595	8554	46672899
Ileus paralytic	25.18	24.75	11	4598	4312	46677141
Pain	25.07	24.75	8	4601	476940	46204513
Respiratory depression	24.75	24.75	15	4594	11585	46669868

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
Neuroleptic malignant syndrome	192.58	21.50	80	5001	16215	29931182
Rhabdomyolysis	89.56	21.50	79	5002	63501	29883896
Water intoxication	89.30	21.50	20	5061	482	29946915
Hepatic function abnormal	88.47	21.50	66	5015	41879	29905518
Pneumonia aspiration	74.23	21.50	57	5024	37723	29909674
Altered state of consciousness	69.91	21.50	43	5038	19876	29927521
Salivary hypersecretion	59.67	21.50	28	5053	7538	29939859
Psychiatric symptom	58.87	21.50	22	5059	3357	29944040
Asphyxia	55.24	21.50	24	5057	5401	29941996
Blood creatine phosphokinase increased	52.89	21.50	50	5031	43798	29903599
Polydipsia	46.89	21.50	19	5062	3594	29943803
White blood cell count increased	41.76	21.50	42	5039	39631	29907766
Delusion	39.81	21.50	25	5056	11964	29935433
Overdose	37.68	21.50	58	5023	84279	29863118
Suicide attempt	37.07	21.50	38	5043	36659	29910738
Toxicity to various agents	35.85	21.50	87	4994	177096	29770301
Lymphocyte percentage increased	34.70	21.50	8	5073	220	29947177
Parkinsonism	34.23	21.50	19	5062	7250	29940147
Stupor	33.14	21.50	14	5067	2939	29944458
Sciatic nerve neuropathy	30.57	21.50	6	5075	74	29947323
Sciatic nerve injury	29.00	21.50	6	5075	98	29947299
Insomnia	27.00	21.50	53	5028	93283	29854114
Persecutory delusion	26.90	21.50	11	5070	2129	29945268
Liver disorder	26.83	21.50	29	5052	29693	29917704
Hallucination, auditory	26.59	21.50	18	5063	9771	29937626
Somnolence	25.67	21.50	53	5028	96710	29850687
Mania	25.26	21.50	17	5064	9137	29938260
Intentional overdose	23.57	21.50	32	5049	41449	29905948
Sudden death	23.25	21.50	20	5061	15472	29931925
Seizure	22.74	21.50	51	5030	98424	29848973
Delirium	22.56	21.50	31	5050	40600	29906797
Depressed level of consciousness	22.50	21.50	30	5051	38192	29909205
Neonatal asphyxia	22.13	21.50	6	5075	323	29947074

Pharmacologic Action:

Source	Code	Description
ATC	N05CD03	NERVOUS SYSTEM PSYCHOLEPTICS HYPNOTICS AND SEDATIVES Benzodiazepine derivatives
MeSH PA	D014151	Anti-Anxiety Agents
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D018682	GABA Agents
MeSH PA	D018757	GABA Modulators
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D011619	Psychotropic Drugs
MeSH PA	D014149	Tranquilizing Agents
CHEBI has role	CHEBI:35474	minor tranquilisers
CHEBI has role	CHEBI:35717	sedatives
CHEBI has role	CHEBI:91016	gabaa receptor agonists

Drug Use (View source of the data)

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	1.89	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
Gamma-aminobutyric acid receptor subunit alpha-3	Ion channel	P34903	GBRA3_HUMAN	ALLOSTERIC MODULATOR	Ki	7.80	IUPHAR	IUPHAR
Gamma-aminobutyric acid receptor subunit alpha-5	Ion channel	P31644	GBRA5_HUMAN	ALLOSTERIC MODULATOR	Ki	8.26	IUPHAR	IUPHAR
Gamma-aminobutyric acid receptor subunit alpha-1	Ion channel	P14867	GBRA1_HUMAN	ALLOSTERIC MODULATOR	Ki	8.28	IUPHAR	IUPHAR
Gamma-aminobutyric acid receptor subunit alpha-2	Ion channel	P47869	GBRA2_HUMAN	ALLOSTERIC MODULATOR	Ki	8.28	IUPHAR	IUPHAR
GABA-A receptor alpha-2/beta-3/gamma-2	Ion channel	P18507 P28472 P47869	GBRA2_HUMAN GBRB3_HUMAN GBRG2_HUMAN		Ki	8.70	WOMBAT-PK
GABA A receptor alpha-3/beta-2/gamma-2	Ion channel	P18507 P34903 P47870	GBRA3_HUMAN GBRB2_HUMAN GBRG2_HUMAN		Ki	8.82	WOMBAT-PK
GABA-A receptor alpha-3/beta-3/gamma-2	Ion channel	P18507 P28472 P34903	GBRA3_HUMAN GBRB3_HUMAN GBRG2_HUMAN		Ki	8.35	WOMBAT-PK
GABA A receptor alpha-3/beta-2/gamma-3	Ion channel	P34903 P47870 Q99928	GBRA3_HUMAN GBRB2_HUMAN GBRG3_HUMAN		Ki	7.50	WOMBAT-PK
GABA A receptor alpha-5/beta-2/gamma-2	Ion channel	P18507 P31644 P47870	GBRA5_HUMAN GBRB2_HUMAN GBRG2_HUMAN		Ki	9	WOMBAT-PK
GABA A receptor alpha-5/beta-2/gamma-3	Ion channel	P31644 P47870 Q99928	GBRA5_HUMAN GBRB2_HUMAN GBRG3_HUMAN		Ki	8.42	WOMBAT-PK
GABA A receptor alpha-5/beta-3/gamma-3	Ion channel	P28472 P31644 Q99928	GBRA5_HUMAN GBRB3_HUMAN GBRG3_HUMAN		Ki	8.42	WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-3	Ion channel	P14867 P47870 Q99928	GBRA1_HUMAN GBRB2_HUMAN GBRG3_HUMAN		Ki	7.46	WOMBAT-PK
GABA-A receptor alpha-1/beta-3/gamma-2	Ion channel	P14867 P18507 P28472	GBRA1_HUMAN GBRB3_HUMAN GBRG2_HUMAN		Ki	8.47	WOMBAT-PK
GABA-A receptor alpha-5/beta-3/gamma-2	Ion channel	P18507 P28472 P31644	GBRA5_HUMAN GBRB3_HUMAN GBRG2_HUMAN		Ki	8.84	WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-2	Ion channel	P14867 P18507 P47870	GBRA1_HUMAN GBRB2_HUMAN GBRG2_HUMAN		Ki	8.70	WOMBAT-PK
GABA-A receptor; anion channel	Ion channel		GBRA1_RAT GBRA2_RAT GBRA3_RAT GBRA4_RAT GBRA5_RAT GBRA6_RAT GBRB1_RAT GBRB2_RAT GBRB3_RAT GBRD_RAT GBRE_RAT GBRG1_RAT GBRG2_RAT GBRG3_RAT GBRP_RAT Q91ZM7_RAT		IC50	8.82	CHEMBL

External reference:

ID	Source
N0000166924	NUI
D01230	KEGG_DRUG
C0016296	UMLSCUI
CHEBI:31622	CHEBI
CHEMBL13280	ChEMBL_ID
DB01544	DRUGBANK_ID
D005445	MESH_DESCRIPTOR_UI
4193	IUPHAR_LIGAND_ID
2951	INN_ID
620X0222FQ	UNII
3380	PUBCHEM_CID
4460	RXNORM
004091	NDDF
387573007	SNOMEDCT_US
96237009	SNOMEDCT_US

Pharmaceutical products:

None