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Routes of administration | Oral |
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Metabolism | Hepatic |
Excretion | Renal |
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Chemical and physical data | |
Formula | C19H18ClN3O |
Molar mass | 339.82 g·mol−1 |
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Cyprazepam [1] is a drug which is a sedative-hypnotic benzodiazepine derivative. [2] [3] [4] [5] It has anxiolytic properties, [6] and presumably also has hypnotic, skeletal muscle relaxant, anticonvulsant and amnestic properties.
The lactam moiety in benzodiazepams is active towards nucleophiles and numerous analogues have been made by exploiting this fact.
For example, heating demoxepam with N-cyclopropylmethylamine leads to amidine formation, the minor tranquilizer cyprazepam.
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.
Flunitrazepam, also known as Rohypnol among other names, is a benzodiazepine used to treat severe insomnia and assist with anesthesia. As with other hypnotics, flunitrazepam has been advised to be prescribed only for short-term use or by those with chronic insomnia on an occasional basis.
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.
Temazepam 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. Many studies, some going as far back as the early 1980s out of Australia and the United Kingdom, both of which have had serious temazepam abuse epidemics and related mortality, have all mostly corroborated each other and proven that the potential for abuse and physical dependence is very high, even in comparison to many other benzodiazepines. As a result, prescriptions for hypnotics such as temazepam have seen a dramatic decrease since 2010, while anxiolytics such as alprazolam (Xanax), clonazepam, and lorazepam (Ativan) 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.
Alprazolam, sold under the brand name Xanax, is a fast-acting, potent tranquilizer of moderate duration within the triazolobenzodiazepine group of chemicals called benzodiazepines. Alprazolam is most commonly used in management of anxiety disorders, specifically panic disorder or generalized anxiety disorder (GAD). Other uses include the treatment of chemotherapy-induced nausea, together with other treatments. GAD improvement occurs generally within a week. Alprazolam is generally taken orally.
Zolpidem, sold under the brand name Ambien among others, is a medication primarily used for the short-term treatment of sleeping problems. Guidelines recommend that it be used only after cognitive behavioral therapy for insomnia and behavioral changes, such as sleep hygiene, have been tried. It decreases the time to sleep onset by about fifteen minutes and at larger doses helps people stay asleep longer. It is taken by mouth and is available in conventional tablets, sublingual tablets, or oral spray.
Triazolam, sold under the brand name Halcion among others, is a central nervous system (CNS) depressant tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepine (BZD) derivatives. It possesses pharmacological properties similar to those of other benzodiazepines, but it is generally only used as a sedative to treat severe insomnia. In addition to the hypnotic properties, triazolam's amnesic, anxiolytic, sedative, anticonvulsant, and muscle relaxant properties are pronounced as well.
Zopiclone, sold under the brand name Imovane among others, is a nonbenzodiazepine used to treat difficulty sleeping. Zopiclone is molecularly distinct from benzodiazepine drugs and is classed as a cyclopyrrolone. However, zopiclone increases the normal transmission of the neurotransmitter gamma-aminobutyric acid (GABA) in the central nervous system, via modulating GABAA receptors similarly to the way benzodiazepine drugs do.
Nitrazepam, sold under the brand name Mogadon among others, is a hypnotic drug of the benzodiazepine class used for short-term relief from severe, disabling anxiety and insomnia. It also has sedative (calming) properties, as well as amnestic, anticonvulsant, and skeletal muscle relaxant effects.
Flurazepam is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. It produces a metabolite with a long half-life, which may stay in the bloodstream for days. Flurazepam was patented in 1968 and came into medical use the same year. Flurazepam, developed by Roche Pharmaceuticals was one of the first benzo hypnotics to be marketed.
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.
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.
Fludiazepam, marketed under the brand name Erispan (エリスパン) is a potent benzodiazepine and 2ʹ-fluoro derivative of diazepam, originally developed by Hoffmann-La Roche in the 1960s. It is marketed in Japan and Taiwan. It exerts its pharmacological properties via enhancement of GABAergic inhibition. Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam. It possesses anxiolytic, anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties. Fludiazepam has been used recreationally.
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.
Zolazepam (Flupyrazapon) is a pyrazolodiazepinone derivative structurally related to the benzodiazepine drugs, which is used as an anaesthetic for a wide range of animals in veterinary medicine. Zolazepam is usually administered in combination with other drugs such as the NMDA antagonist tiletamine or the α2 adrenergic receptor agonist xylazine, depending on what purpose it is being used for. It is around four times the potency of diazepam but it is both water-soluble and un-ionized at physiological pH meaning that its onset is very fast.
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.
Flutazolam is a drug which is a benzodiazepine derivative. It was invented in Japan, and this is the main country in which it has been used medically. It has sedative, muscle relaxant, anticonvulsant, and anxiolytic effects similar to those produced by other benzodiazepine derivatives, and though it is around the same potency as diazepam, it produces a more marked sedation and impaired coordination. It is indicated for the treatment of insomnia. Its major active metabolite is n-desalkylflurazepam, also known as norflurazepam, which is also a principal metabolite of flurazepam. While flutazolam has a very short half-life of only 3.5 hours, n-desalkylflurazepam has a long half-life of between 47–100 hours.
Flutoprazepam (Restas) is a drug which is a benzodiazepine. It was patented in Japan by Sumitomo in 1972 and its medical use remains mostly confined to that country. Its muscle relaxant properties are approximately equivalent to those of diazepam - however, it has more powerful sedative, hypnotic, anxiolytic and anticonvulsant effects and is around four times more potent by weight compared to diazepam. It is longer acting than diazepam due to its long-acting active metabolites, which contribute significantly to its effects. Its principal active metabolite is n-desalkylflurazepam, also known as norflurazepam, which is also a principal metabolite of flurazepam.
Sulazepam is a benzodiazepine derivative. It is the thioamide derivative of diazepam. It is metabolised into diazepam, desmethyldiazepam and oxydiazepam. It has sedative, muscle relaxant, hypnotic, anticonvulsant and anxiolytic properties like those of other benzodiazepines. It was never marketed.
JM-1232 is a sedative and hypnotic drug being researched as a potential anesthetic. It has similar effects to sedative-hypnotic benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine hypnotic. It was developed by a team at Maruishi Pharmaceutica.