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Flutemazepam

Chemical compound


Chemical compound

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid477394733
IUPAC_name7-chloro-5-(2-fluorophenyl)-3-hydroxy-1-methyl-3*H*-1,4-benzodiazepin-2-one
imageFlutemazepam structure.svg
image_classskin-invert-image
width200
pregnancy_AU
pregnancy_US
legal_CASchedule IV
legal_DENpSG
legal_UKPSA
CAS_number_Ref
CAS_number52391-89-6
ChEMBL_Ref
ChEMBL291770
PubChem40344
DrugBank_Ref
UNII_Ref
UNIIJ8U5694BCW
ChemSpiderID_Ref
ChemSpiderID36859
smilesFC1=CC=CC=C1C2=NC(C(N(C)C3=C2C=C(C=C3)Cl)=O)O
StdInChI_Ref
StdInChI1S/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
StdInChIKey_Ref
StdInChIKeyRMFYWNFETXNTIQ-UHFFFAOYSA-N
C16H=12Cl=1F=1N=2O=2

| elimination_half-life =

Flutemazepam was initially first synthesized in 1965, but was not further described until a team at Stabilimenti Chimici Farmaceutici Riuniti SpA in the mid-1970s. 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. Flutemazepam has been shown to have similar pharmacological properties to temazepam, but with more powerful sedative-hypnotic and anxiolytic properties. 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. Flutemazepam is highly effective for acute psychotic states, especially stimulant psychosis, violent behaviour, and aggression.

It was first synthesized and described in 1965 by Leo Sternbach. 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 administration, 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.

References

References

  1. "Benzodiazepine Compounds for Therapeutical Use".
  2. "Flutemazepam". National Library of Medicine.
  3. "Flutemazepam". United States Biological.
  4. "Temazepam Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD".
  5. "flutemazepam". psychotropics.dk.
  6. (1999). "Concise Dictionary of Pharmacological Agents". Springer.
  7. (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.
  8. "PubChem Compound Summary for CID 40344, Flutemazepam". National Center for Biotechnology Information (2022).
  9. "Process for the preparation of 3-fluorobenzodiazepines". US Patent US4120856A.
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