Flutemazepam
Flutemazepam structure.svg
Clinical data
Pregnancy
category
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 7-chloro-5-(2-fluorophenyl)-3-hydroxy-1-methyl-3H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.052.612 Edit this at Wikidata
Chemical and physical data
FormulaC16H12ClFN2O2
Molar mass318.730 g·mol−1
3D model (JSmol)
  • FC1=CC=CC=C1C2=NC(C(N(C)C3=C2C=C(C=C3)Cl)=O)O
  • 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 checkY
  • Key:RMFYWNFETXNTIQ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Flutemazepam, initially first synthesized in 1965,[1] but wasn't further developed and described until a team at Stabilimenti Chimici Farmaceutici Riuniti SpA in the mid 1970s.[2][3] It is the fluorinated analogue of temazepam that has powerful hypnotic, sedative, amnesiac, anxiolytic, anticonvulsant and skeletal muscle relaxant properties.[4] It is most closely related in structure to temazepam, and as a result flutemazepam has been shown to have similar properties to temazepam, but is approximately 20x more potent by weight than it's parent drug. It has been found to be effective for the treatment of the most severe states of anxiety, panic attacks, and severe insomnia. Furthermore, it is highly potent with approximately 1 mg of flutemazepam being equivalent to 10 mg of diazepam.[5][6][7][8] Flutemazepam is highly effective for acute psychotic states, especially stimulant psychosis, violent behaviour, and aggression.[9]

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. The compound, flutemazepam, is the fluoro instead of chloro analogue of the powerful hypnotic benzodiazepine, temazepam. Of the tested compounds (9 different 3-fluorobenzodiazepines including, a powerful compound known as N-Desalkyl-3-hydroxyflurazepam). Flutemazepam was the most potent: 20x more potent than temazepam, 10x more potent than diazepam, and roughly equipotent to a related 3-hydroxy benzodiazepine, lorazepam. It was also the most rapid-acting compound of the series via oral administration, as well as the most active and powerful anxiolytic, myorelaxant, tranquilizer, motor-impairing, amnesic, sedative-hypnotic, and anti-convulsive agent at doses as low as 0.5-1 mg range.[10]


See also

References

  1. ^ a b "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. ^ "Universal Guide for Temazepam". fastukmeds.com. Retrieved 2022-03-31.
  5. ^ "Flutemazepam". US Biologic. United States Biological. Retrieved 22 July 2022.
  6. ^ "Temazepam Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD". www.webmd.com. Retrieved 2022-03-31.
  7. ^ "flutemazepam". psychotropics.dk. Retrieved 11 February 2009.
  8. ^ Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents. Springer. ISBN 978-0-7514-0499-9.
  9. ^ 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.pub4/14651858.CD003079.pub4. PMC 6486117.
  10. ^ Bingham, EM. "Process for the preparation of 3-fluorobenzodiazepines". Google Patents. US Patent US4120856A. Retrieved 30 July 2022.