Flutemazepam

Last updated
Flutemazepam
Flutemazepam structure.svg
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 InfoCard 100.052.612 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H12ClFN2O2
Molar mass 318.730 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 Yes check.svgY
  • Key:RMFYWNFETXNTIQ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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 the 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. 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 nitrazepam, 5x more potent than nimetazepam 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. [9]

See also

Related Research Articles

<span class="mw-page-title-main">Benzodiazepine</span> Class of depressant drugs

Benzodiazepines, colloquially called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, insomnia, and seizures. The first benzodiazepine, chlordiazepoxide (Librium), was discovered accidentally by Leo Sternbach in 1955 and was made available in 1960 by Hoffmann–La Roche, who soon followed with diazepam (Valium) in 1963. By 1977, benzodiazepines were the most prescribed medications globally; the introduction of selective serotonin reuptake inhibitors (SSRIs), among other factors, decreased rates of prescription, but they remain frequently used worldwide.

<span class="mw-page-title-main">Diazepam</span> Benzodiazepine sedative

Diazepam, first marketed as Valium, is a medicine of the benzodiazepine family that acts as an anxiolytic. It is commonly used to treat a range of conditions, including anxiety, seizures, alcohol withdrawal syndrome, muscle spasms, insomnia, and restless legs syndrome. It may also be used to cause memory loss during certain medical procedures. It can be taken orally, as a suppository inserted into the rectum, intramuscularly, intravenously or used as a nasal spray. When injected intravenously, effects begin in one to five minutes and last up to an hour. Orally, effects begin after 15 to 60 minutes.

<span class="mw-page-title-main">Temazepam</span> Insomnia medication

Temazepam, sold under the brand name Restoril among others, is a medication of the benzodiazepine class which is generally used to treat severe or debilitating insomnia. It is taken by mouth. Temazepam is rapidly absorbed, and significant hypnotic effects begin in less than 30 minutes and can last for up to eight hours. Prescriptions for hypnotics such as temazepam have seen a dramatic decrease since 2010, while anxiolytics such as alprazolam, clonazepam, and lorazepam have increased or remained stable. Temazepam and similar hypnotics, such as triazolam (Halcion) are generally reserved for severe and debilitating insomnia. They have largely been replaced by z-drugs and atypical antidepressants as first line treatment for insomnia.

<span class="mw-page-title-main">Oxazepam</span> Benzodiazepine medication

Oxazepam is a short-to-intermediate-acting benzodiazepine. Oxazepam is used for the treatment of anxiety and insomnia and in the control of symptoms of alcohol withdrawal syndrome.

<span class="mw-page-title-main">Estazolam</span> Tranquilizer

Estazolam, sold under the brand name Prosom among others, is a tranquilizer medication of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. Estazolam is an intermediate-acting oral benzodiazepine. It is used for short-term treatment of insomnia.

<span class="mw-page-title-main">Nordazepam</span> Benzodiazepine derivative medication

Nordazepam is a 1,4-benzodiazepine derivative. Like other benzodiazepine derivatives, it has amnesic, anticonvulsant, anxiolytic, muscle relaxant, and sedative properties. However, it is used primarily in the treatment of anxiety disorders. It is an active metabolite of diazepam, chlordiazepoxide, clorazepate, prazepam, pinazepam, and medazepam.

<span class="mw-page-title-main">Clorazepate</span> Benzodiazepine medication

Clorazepate, sold under the brand name Tranxene among others, is a benzodiazepine medication. It possesses anxiolytic, anticonvulsant, sedative, hypnotic, and skeletal muscle relaxant properties. Clorazepate is an unusually long-lasting benzodiazepine and serves as a prodrug for the equally long-lasting desmethyldiazepam, which is rapidly produced as an active metabolite. Desmethyldiazepam is responsible for most of the therapeutic effects of clorazepate.

<span class="mw-page-title-main">Loprazolam</span> Benzodiazepine

Loprazolam (triazulenone) marketed under many brand names is a benzodiazepine medication. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. It is licensed and marketed for the short-term treatment of moderately-severe insomnia.

<span class="mw-page-title-main">Nimetazepam</span> Benzodiazepine medication

Nimetazepam is an intermediate-acting hypnotic drug which is a benzodiazepine derivative. It was first synthesized by a team at Hoffmann-La Roche in 1964. It possesses powerful hypnotic, anxiolytic, sedative, and skeletal muscle relaxant properties. Nimetazepam is also a particularly potent anticonvulsant. It is marketed in 5 mg tablets known as Erimin, which is the brand name manufactured and marketed by the large Japanese corporation Sumitomo. Japan is the sole manufacturer of nimetazepam in the world. Outside of Japan, Erimin is available in much of East and Southeast Asia and was widely prescribed for the short-term treatment of severe insomnia in patients who have difficulty falling asleep or maintaining sleep. Sumitomo has ceased manufacturing Erimin since November 2015. It is still available as a generic drug or as Lavol.

<span class="mw-page-title-main">Camazepam</span> Chemical compound

Camazepam is a benzodiazepine psychoactive drug, marketed under the brand names Albego, Limpidon and Paxor. It is the dimethyl carbamate ester of temazepam, a metabolite of diazepam. While it possesses anxiolytic, anticonvulsant, skeletal muscle relaxant and hypnotic properties it differs from other benzodiazepines in that its anxiolytic properties are particularly prominent but has comparatively limited anticonvulsant, hypnotic and skeletal muscle relaxant properties.

<span class="mw-page-title-main">Etizolam</span> Chemical compound

Etizolam is a thienodiazepine derivative which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring and triazole ring has been fused, making the drug a thienotriazolodiazepine.

<span class="mw-page-title-main">Clotiazepam</span> Chemical compound

Clotiazepam is a thienodiazepine drug which is a benzodiazepine analog. The clotiazepam molecule differs from benzodiazepines in that the benzene ring has been replaced by a thiophene ring. It possesses anxiolytic, skeletal muscle relaxant, anticonvulsant, sedative properties. Stage 2 NREM sleep is significantly increased by clotiazepam.

<span class="mw-page-title-main">Lormetazepam</span> Benzodiazepine medication

Lormetazepam, sold under the brand name Noctamid among others, is a drug which is a short to intermediate acting 3-hydroxy benzodiazepine derivative and temazepam analogue. It possesses hypnotic, anxiolytic, anticonvulsant, sedative, and skeletal muscle relaxant properties.

<span class="mw-page-title-main">Brotizolam</span> Benzodiazepine

Brotizolam is a sedative-hypnotic thienotriazolodiazepine drug which is a benzodiazepine analog. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties, and is considered to be similar in effect to other short-acting hypnotic benzodiazepines such as triazolam or midazolam. It is used in the short-term treatment of severe insomnia. Brotizolam is a highly potent and short-acting hypnotic, with a typical dose ranging from 0.125 to 0.25 milligrams, which is rapidly eliminated with an average half-life of 4.4 hours.

<span class="mw-page-title-main">Chlordiazepoxide</span> Benzodiazepine class sedative and hypnotic medication

Chlordiazepoxide, trade name Librium among others, is a sedative and hypnotic medication of the benzodiazepine class; it is used to treat anxiety, insomnia and symptoms of withdrawal from alcohol and other drugs.

<span class="mw-page-title-main">Delorazepam</span> Benzodiazepine medication

Delorazepam, also known as chlordesmethyldiazepam and nordiclazepam, is a drug which is a benzodiazepine and a derivative of desmethyldiazepam. It is marketed in Italy, where it is available under the trade name EN and Dadumir. Delorazepam (chlordesmethyldiazepam) is also an active metabolite of the benzodiazepine drugs diclazepam and cloxazolam. Adverse effects may include hangover type effects, drowsiness, behavioural impairments and short-term memory impairments. Similar to other benzodiazepines delorazepam has anxiolytic, skeletal muscle relaxant, hypnotic and anticonvulsant properties.

<span class="mw-page-title-main">Benzoctamine</span> Chemical compound

Benzoctamine is a drug that possesses sedative and anxiolytic properties. Marketed as Tacitin by Ciba-Geigy, it is different from most sedative drugs because in most clinical trials it does not produce respiratory depression, but actually stimulates the respiratory system. As a result, when compared to other sedative and anxiolytic drugs such as benzodiazepines like diazepam, it is a safer form of tranquilizing. However, when co-administered with other drugs that cause respiratory depression, like morphine, it can cause increased respiratory depression.

<span class="mw-page-title-main">Fosazepam</span> Benzodiazepam

Fosazepam is a drug which is a benzodiazepine derivative; it is a water soluble derivative of diazepam. It has sedative and anxiolytic effects, and is a derivative of diazepam which has been substituted with a dimethylphosphoryl group to improve solubility in water.

<span class="mw-page-title-main">Metaclazepam</span> Chemical compound

Metaclazepam is a drug which is a benzodiazepine derivative. It is a relatively selective anxiolytic with less sedative or muscle relaxant properties than other benzodiazepines such as diazepam or bromazepam. It has an active metabolite N-desmethylmetaclazepam, which is the main metabolite of metaclazepam. There is no significant difference in metabolism between younger and older individuals.

<span class="mw-page-title-main">Premazepam</span> Chemical compound

Premazepam is a Pyrrolodiazepine class of drug. It is a partial agonist of benzodiazepine receptors and was shown in 1984 to possess both anxiolytic and sedative properties in humans but was never marketed.

References

  1. 1 2 "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.