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

Stem definitionDrug idCAS RN
diazepam derivatives 1218 17617-23-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • flurazepam
  • stauroderm
  • flurazepam hydrochloride
  • flurazepam HCl
A benzodiazepine derivative used mainly as a hypnotic.
  • Molecular weight: 387.88
  • Formula: C21H23ClFN3O
  • CLOGP: 4.22
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 35.91
  • ALOGS: -4.59
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
30 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 500 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.10 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 83 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
April 7, 1970 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Sopor 765.48 29.48 196 3602 20888 53324380
Drug abuse 662.24 29.48 226 3572 65300 53279968
Intentional self-injury 366.58 29.48 115 3683 25169 53320099
Suicide attempt 269.69 29.48 114 3684 58054 53287214
Intentional overdose 228.54 29.48 106 3692 67099 53278169
Overdose 140.20 29.48 90 3708 107646 53237622
Bradyphrenia 137.56 29.48 40 3758 6710 53338558
Toxicity to various agents 117.50 29.48 108 3690 219490 53125778
Coma 78.67 29.48 51 3747 61732 53283536
Bradykinesia 67.90 29.48 21 3777 4332 53340936
Anoxia 52.28 29.48 10 3788 268 53345000
Substance abuse 43.06 29.48 15 3783 4479 53340789
Hypokinesia 42.40 29.48 20 3778 13007 53332261
Completed suicide 39.71 29.48 49 3749 138152 53207116
Mydriasis 38.75 29.48 18 3780 11308 53333960
Cerebellar infarction 37.27 29.48 11 3787 1935 53343333
Sedation 36.50 29.48 24 3774 29651 53315617
Confusional state 36.39 29.48 56 3742 194165 53151103
Hypotension 33.97 29.48 63 3735 254013 53091255
Drug interaction 31.35 29.48 56 3742 219273 53125995

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 200.07 29.25 99 2007 80144 32431276
Sopor 186.21 29.25 56 2050 11693 32499727
Intentional self-injury 94.29 29.25 35 2071 13865 32497555
Toxicity to various agents 52.73 29.25 61 2045 177980 32333440
Completed suicide 52.08 29.25 45 2061 92472 32418948
Psychomotor hyperactivity 47.78 29.25 19 2087 9020 32502400
Suicide attempt 44.99 29.25 29 2077 38215 32473205
Intentional overdose 40.39 29.25 28 2078 41573 32469847
Bradyphrenia 40.16 29.25 14 2092 4615 32506805
Sciatic nerve neuropathy 36.12 29.25 6 2100 77 32511343
Hepatic fibrosis 35.50 29.25 12 2094 3606 32507814
Sciatic nerve injury 34.77 29.25 6 2100 98 32511322
Electrocardiogram QT prolonged 30.10 29.25 23 2083 39618 32471802
Bronchial aspiration procedure 29.76 29.25 5 2101 69 32511351
Stupor 29.60 29.25 10 2096 2999 32508421

Pharmacologic Action:

SourceCodeDescription
ATC N05CD01 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Benzodiazepine derivatives
FDA CS M0002356 Benzodiazepines
CHEBI has role CHEBI:35474 minor tranquilisers
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:35717 sedatives
CHEBI has role CHEBI:91016 GABAA receptor agonists
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 D006993 Hypnotics and Sedatives
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
FDA EPC N0000175694 Benzodiazepine

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Insomnia indication 193462001
Suicidal thoughts contraindication 6471006
Disorder of lung contraindication 19829001 DOID:850
Borderline personality disorder contraindication 20010003 DOID:10930
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Depressive disorder contraindication 35489007
Substance abuse contraindication 66214007
Psychotic disorder contraindication 69322001
Sleep apnea contraindication 73430006 DOID:0050847
Decreased respiratory function contraindication 80954004
Kidney disease contraindication 90708001 DOID:557
Hypoalbuminemia contraindication 119247004
Disease of liver contraindication 235856003 DOID:409
Sleep automatism contraindication 247962006
Pregnancy, function contraindication 289908002
Coma contraindication 371632003
Breastfeeding (mother) contraindication 413712001
Porphyria contraindication 418470004
Behavioral Disorders contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.24 Basic
pKa2 1.92 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR IC50 8.10 WOMBAT-PK CHEMBL
Solute carrier family 22 member 2 Transporter IC50 4.22 WOMBAT-PK

External reference:

IDSource
4019763 VUID
N0000147854 NUI
D00329 KEGG_DRUG
1172-18-5 SECONDARY_CAS_RN
4017827 VANDF
4019763 VANDF
C0016375 UMLSCUI
CHEBI:5128 CHEBI
FL7 PDB_CHEM_ID
CHEMBL3989724 ChEMBL_ID
CHEMBL968 ChEMBL_ID
DB00690 DRUGBANK_ID
D005479 MESH_DESCRIPTOR_UI
3393 PUBCHEM_CID
7188 IUPHAR_LIGAND_ID
2551 INN_ID
IHP475989U UNII
4501 RXNORM
4752 MMSL
70 MMSL
d00238 MMSL
001463 NDDF
004584 NDDF
19403009 SNOMEDCT_US
27928002 SNOMEDCT_US
387109000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Flurazepam Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-4415 CAPSULE 15 mg ORAL ANDA 27 sections
Flurazepam Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-4430 CAPSULE 30 mg ORAL ANDA 27 sections
Flurazepam HUMAN PRESCRIPTION DRUG LABEL 1 21695-363 CAPSULE 30 mg ORAL ANDA 19 sections
Flurazepam HUMAN PRESCRIPTION DRUG LABEL 1 52959-236 CAPSULE 30 mg ORAL ANDA 19 sections
Flurazepam Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-0092 CAPSULE 15 mg ORAL ANDA 14 sections
Flurazepam Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-0093 CAPSULE 30 mg ORAL ANDA 14 sections
Flurazepam Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55289-038 CAPSULE 30 mg ORAL ANDA 26 sections