Fludiazepam

Fludiazepam,^[2] marketed under the brand name Erispan (エリスパン)^[3]^[4] is a potent benzodiazepine and 2ʹ-fluoro derivative of diazepam,^[5] originally developed by Hoffmann-La Roche in the 1960s.^[6] It is marketed in Japan and Taiwan. ^{[citation needed]} It exerts its pharmacological properties via enhancement of GABAergic inhibition.^[7] Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam.^[8] It possesses anxiolytic,^[9]^[10]^[11] anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties.^[12] Fludiazepam has been used recreationally.^[13]

Trade namesErispan (JP, TW)

AHFS/Drugs.comInternational Drug Names

Routes of
administrationOral (tablets)

Drug classBenzodiazepine

Quick facts Clinical data, Trade names ...

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
PubChem CID	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
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References

[1]
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. Retrieved 2023-08-16.
[2]
US Patent 3371085 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones
[3]
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.
[4]
"Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2008-12-29.
[5]
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.
[6]
US Patent 3299053 -ARYL-JH-L,X-BENZODIAZEPIN-Z(LH)-ONES
[7]
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.
[8]
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.
[9]
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.
[10]
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.
[11]
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.
[12]
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.
[13]
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.

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