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Fludiazepam

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Fludiazepam
Clinical data


Trade names	Erispan (JP,TW)
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral (tablets)
Drug class	Benzodiazepine
ATC code	N05BA17 (WHO)
Legal status
Legal status	BR: Class B1 (Psychoactive drugs)^[1] CA: Schedule IV DE: Anlage III (Special prescription form required) US: Schedule IV
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name 7-chloro-5-(2-fluorophenyl)-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
CAS Number	3900-31-0^Y
PubChemCID	3369
DrugBank	DB01567^Y
ChemSpider	3252^Y
UNII	7F64A2K16Z
KEGG	D01354^Y
ChEBI	CHEBI:31618^Y
ChEMBL	ChEMBL13291^Y
CompTox Dashboard(EPA)	DTXSID00192277
ECHA InfoCard	100.292.343
Chemical and physical data
Formula	C₁₆H₁₂ClFN₂O
Molar mass	302.73 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1CN=C(C2=CC=CC=C2F)C3=CC(Cl)=CC=C3N1C
InChI InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3^Y Key:ROYOYTLGDLIGBX-UHFFFAOYSA-N^Y
(verify)

Fludiazepam,^[2] marketed under the brand nameErispan (エリスパン)^[3]^[4] is a potentbenzodiazepine and 2ʹ-fluoro derivative ofdiazepam,^[5] originally developed byHoffmann-La Roche in the 1960s.^[6] It is marketed inJapan andTaiwan.^{[citation needed]} It exerts its pharmacological properties via enhancement of GABAergic inhibition.^[7] Fludiazepam has 4 times more binding affinity forbenzodiazepine receptors thandiazepam.^[8] It possessesanxiolytic,^[9]^[10]^[11]anticonvulsant,sedative,hypnotic andskeletal muscle relaxant properties.^[12] Fludiazepam has been used recreationally.^[13]

References

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^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
^ US Patent 3371085 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones
^Su TP, Chen TJ, Hwang SJ, Chou LF, Fan AP, Chen YC (August 2002). "Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000".Zhonghua Yi Xue Za Zhi (Chinese Medical Journal; Free China Ed).65 (8):378–91.PMID 12455808.
^"Benzodiazepine Names". non-benzodiazepines.org.uk. Archived fromthe original on 2008-12-08. Retrieved2008-12-29.
^Neville GA, Beckstead HD, Shurvell HF (February 1994). "A Fourier transform-Raman and infrared vibrational study of delorazepam, fludiazepam, flurazepam, and tetrazepam".Journal of Pharmaceutical Sciences.83 (2):143–51.doi:10.1002/jps.2600830207.PMID 7909552.
^US Patent 3299053 -ARYL-JH-L,X-BENZODIAZEPIN-Z(LH)-ONES
^Tsuchiya T, Fukushima H (April 1978). "Effects of benzodiazepines and pentobarbitone on the gaba-ergic recurrent inhibition of hippocampal neurons".European Journal of Pharmacology.48 (4):421–4.doi:10.1016/0014-2999(78)90169-3.PMID 648585.
^Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A (January 1985). "Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity".Life Sciences.36 (2):113–9.doi:10.1016/0024-3205(85)90089-X.PMID 2857046.
^Okada S, Ichiki K, Tanokuchi S, Ishii K, Hamada H, Ota Z (1994). "Effect of an anxiolytic on lipid profile in non-insulin-dependent diabetes mellitus".The Journal of International Medical Research.22 (6):338–42.doi:10.1177/030006059402200605.PMID 7895897.S2CID 9591519.
^Okada S, Ichiki K, Tanokuchi S, Ishii K, Hamada H, Ota Z (1995). "Improvement of stress reduces glycosylated haemoglobin levels in patients with type 2 diabetes".The Journal of International Medical Research.23 (2):119–22.doi:10.1177/030006059502300205.PMID 7601294.S2CID 12865838.
^Okada S, Ichiki K, Tanokuchi S, Ishii K, Hamada H, Ota Z (1995). "How blood pressure in patients with non-insulin-dependent diabetes mellitus is influenced by stress".The Journal of International Medical Research.23 (5):377–80.doi:10.1177/030006059502300508.PMID 8529781.S2CID 42485678.
^Inoue H, Maeno Y, Iwasa M, Matoba R, Nagao M (September 2000). "Screening and determination of benzodiazepines in whole blood using solid-phase extraction and gas chromatography/mass spectrometry".Forensic Science International.113 (1–3):367–73.doi:10.1016/S0379-0738(00)00226-7.PMID 10978650.
^Shimamine M, Masunari T, Nakahara Y (1993). "[Studies on identification of drugs of abuse by diode array detection. I. Screening-test and identification of benzodiazepines by HPLC-DAD with ICOS software system]".Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences (111):47–56.PMID 7920567.

External links

[edit]

"エリスパンフルジアゼパム錠0.25mg，細粒0.1% Erispan (fludiazepam tablets 0.25 mg, fine granules 0.1%) Prescribing Information" (in Japanese). Sumitomo Dainippon Pharma.^{[permanent dead link]}
(in Japanese)Official Dainippon Sumitomo Pharma Website Archived 2020-07-01 at theWayback Machine

v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite ofRilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (notGABA_A receptor ligands)

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptoragonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines:Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam;Others:Alpidem^‡ Barbiturates (e.g.,phenobarbital) Carbamates (e.g.,meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g.,escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g.,duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g.,trazodone) TCAsTooltip Tricyclic antidepressants (e.g.,clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g.,mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g.,phenelzine);Others:Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g.,prazosin) Alpha-2 agonists (e.g.,clonidine,dexmedetomidine,guanfacine) Beta blockers (e.g.,propranolol,atenolol,betaxolol,nadolol,oxprenolol,pindolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e GABA_A receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g.,baicalin) Wogonin
Imidazoles	Etomidate Metomidate Methoxyetomidate Propoxate Isopropoxate Butomidate Iso-butomidate Sec-butomidate CF2-Etomidate CF3-Etomidate CF3-Propoxate Flutomidate 2,6-Dichloro-3-fluoroetomidate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certainanabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones:Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines:Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines:Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others:Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) Miltirone (rosmariquinone) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Cipepofol Fospropofol Propofol Propofol hemisuccinate Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g.,ivermectin) Bromide compounds (e.g.,lithium bromide,potassium bromide,sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g.,dihydroergocryptine,dihydroergosine,dihydroergotamine,ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g.,flufenamic acid,mefenamic acid,niflumic acid,tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g.,4-O-methylhonokiol,honokiol,magnolol,obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Nicotinic acid Nicotinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g.,sulfonmethane (sulfonal),tetronal,trional) Terpenoids (e.g.,borneol) Topiramate Valerian constituents (e.g.,isovaleric acid,isovaleramide,valerenic acid,valerenol) Unsorted benzodiazepine site positive modulators:α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also:Receptor/signaling modulators •GABA receptor modulators •GABA metabolism/transport modulators