Flutemazepam

Flutemazepam

Legal status
Legal status	CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 7-chloro-5-(2-fluorophenyl)-3-hydroxy-1-methyl-3H-1,4-benzodiazepin-2-one
CAS Number	52391-89-6^N
PubChem CID	40344
ChemSpider	36859^Y
UNII	J8U5694BCW
ChEMBL	ChEMBL291770^Y
CompTox Dashboard (EPA)	DTXSID10866255
ECHA InfoCard	100.052.612
Chemical and physical data
Formula	C16H12ClFN2O2
Molar mass	318.73 g·mol^−1
3D model (JSmol)	Interactive image
SMILES FC1=CC=CC=C1C2=NC(C(N(C)C3=C2C=C(C=C3)Cl)=O)O
InChI InChI=1S/C16H12ClFN2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3^Y Key:RMFYWNFETXNTIQ-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

Flutemazepam was initially first synthesized in 1965,^[1] but was not further described until a team at Stabilimenti Chimici Farmaceutici Riuniti SpA in the mid-1970s.^[2][3] It is a short-acting (9–25 hr elimination half-life) fluorinated analogue of temazepam that has powerful hypnotic, sedative, amnesiac, anxiolytic, anticonvulsant and skeletal muscle relaxant properties. As a result, flutemazepam has been shown to have similar pharmacological properties to temazepam. It has been found to be effective for the treatment of the most severe states of anxiety, panic attacks, and insomnia. Furthermore, it is potent with 1 mg of flutemazepam being equivalent to 10 mg of diazepam.^[4][5][6][7] Flutemazepam is highly effective for acute psychotic states, especially stimulant psychosis, violent behaviour, and aggression.^[8]

It was first synthesized and described in 1965 by Leo Sternbach.^[1] In a test which compared a series of 3-fluorobenzodiazepine compounds in 1976, one of which was the 3-hydroxy benzodiazepine, flutemazepam. There were nine compounds tested (all nine were 3-fluorobenzodiazepines) including, a well known compound known as N-Desalkyl-3-hydroxyflurazepam, or also called norflurazepam ). Flutemazepam was the most potent: 20x more potent than temazepam, 10x more potent than diazepam and nitrazepam, and roughly equipotent to a related 3-hydroxy benzodiazepine, lorazepam. Equipotent to another fluorinated analogue (of nitrazepam), flunitrazepam. Via oral adminitration, 1 mg flutemazepam is equivalent to 10 mg diazepam. Of the nine compounds, flutemazepam was the most rapid-acting compound of the series via oral administration, with noticeable sedative-hypnotic effects beginning 10-15 minutes post-ingestion. At equipotent doses, it was the most active and effective anxiolytic, myorelaxant, tranquilizer, sedative-hypnotic, and anti-convulsive agent at doses as low as 0.5–1 mg range. It had motor-impairing, amnesic, ataxia, and loss of balance as side effects (1–5%), the highest in the series.^[9]

See also

• Benzodiazepine
• Nitemazepam – 7-nitro analogue of temazepam
• Temazepam

References

1. "PubChem Compound Summary for CID 40344, Flutemazepam". National Center for Biotechnology Information (2022). Retrieved 30 July 2022.
2. GB 1431282, "Benzodiazepine Compounds for Therapeutical Use", issued 7 April 1976, assigned to Schiapparelli Farma SpA 
3. "Flutemazepam". PubChem. National Library of Medicine. Retrieved 2022-03-31.
4. "Flutemazepam". US Biologic. United States Biological. Retrieved 22 July 2022.
5. "Temazepam Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD". www.webmd.com. Retrieved 2022-03-31.
6. "flutemazepam". psychotropics.dk. Retrieved 11 February 2009.
7. Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents. Springer. ISBN 978-0-7514-0499-9.
8. Esmailian M, Ahmadi O, Taheri M, Zamani M (September 2015). "Comparison of haloperidol and midazolam in restless management of patients referred to the Emergency Department: A double-blinded, randomized clinical trial". Journal of Research in Medical Sciences. 20 (9): 844–849. doi:10.1002/14651858.CD003079.pub4. PMC 6486117. PMID 29219171.
9. Bingham, EM. "Process for the preparation of 3-fluorobenzodiazepines". Google Patents. US Patent US4120856A. Retrieved 30 July 2022.