Oxazepam
Encyclopedia
Oxazepam is a drug which is a short to intermediate acting 3-hydroxy benzodiazepine
derivative. Oxazepam is a benzodiazepine used extensively since the 1960s for the treatment of anxiety and insomnia and in the control of symptoms of alcohol withdrawal. It is a metabolite of diazepam
, prazepam
and temazepam
. Oxazepam has moderate amnesic, anxiolytic
, anticonvulsant
, hypnotic
, sedative
and skeletal muscle relaxant properties compared to other benzodiazepines.
. Physicians may use Oxazepam outside its approved indications to treat social phobia
, posttraumatic stress disorder, insomnia
, premenstrual syndrome, and other conditions.
In Finland, oxazepam is available generically in the form of 15 mg, 30 mg and 50 mg tablets.
In France, oxazepam is available in the form of 10 mg and 50 mg tablets.
In Australia, oxazepam is available in the form of 5 mg, 7.5 mg, 10 mg, 15 mg and 30 mg tablets.
, retrograde amnesia, but does not affect transient global amnesia
. Side effects due to rapid decrease in dose or abrupt withdrawal from oxazepam may include abdominal and muscle cramps, convulsions, depression, inability to fall asleep or stay asleep, sweating, tremors, or vomiting.
, chronic obstructive pulmonary disease
and limited pulmonary reserve, as well as severe hepatic disease.
in the neonate with symptoms including hypotonia
, and reluctance to suck, to apnoeic spells, cyanosis
, and impaired metabolic responses to cold stress. Floppy infant syndrome and sedation in the new born may also occur. Symptoms of floppy infant syndrome and the neonatal benzodiazepine withdrawal syndrome have been reported to persist from hours to months after birth.
drugs can cause tolerance, physical dependence
, addiction
and what is known as the benzodiazepine withdrawal syndrome
. Withdrawal from oxazepam or other benzodiazepines often leads to withdrawal symptoms which are similar to those seen during alcohol and barbiturate
withdrawal. The higher the dose and the longer the drug is taken the greater the risk of experiencing unpleasant withdrawal symptoms. Withdrawal symptoms can however occur at standard dosages and also after short term use. Benzodiazepine treatment should be discontinued as soon as possible via a slow and gradual dose reduction regimen.
to the GABAA receptor which results in inhibitory effects on the central nervous system
. The half-life
of oxazepam is 4–15 hours. Oxazepam has been shown to suppress cortisol
levels. Oxazepam is the most slowly absorbed benzodiazepine and has the slowest onset of action of all the common benzodiazepines according to one British study.
Oxazepam is an active metabolite formed during the breakdown of diazepam
, nordazepam
, and certain similar drugs. Oxazepam may be safer than many other benzodiazepines in patients with impaired liver function because it does not require hepatic oxidation, but rather it is simply metabolized via glucuronidation
. This means that oxazepam is less likely to accumulate and cause adverse reactions in the elderly or people with liver disease. Oxazepam is similar to lorazepam
in this respect. (1)
There is preferential storage of oxazepam in some organs including the heart of the neonate. Absorption by any administered route and the risk of accumulation is significantly increased in the neonate and it is recommended to withdraw oxazepam during pregnancy and breast feeding as oxazepam is excreted in breast milk.
, there is likely an overlap in possible interactions with other drugs or food, with exception of the pharmacokinetic CYP450 interactions (e.g. with cimetidine
). Take precautions, and follow closely the prescription of your doctor, when taking oxazepam (or other benozodiazepines) in combinations with antidepressant medication (SSRI
s such as Prozac, Zoloft, and Paxil, or multiple reuptake inhibitors such as Wellbutrin, Cymbalta, or Effexor), potent painkillers
(opioids, e.g. morphine
, oxycodone
or methadone
). Concurrent use of these medicines (as well as other benzodiazepine
s) can interact in a way that is difficult to predict. Drinking alcohol when taking oxazepam is not recommended. Concomitant use of oxazepam and alcohol can lead to increased sedation
, severe problems with coordination
(ataxia
e), decreased muscle tone and in severe cases or in predisposed patients even to life-threatening intoxications with respiratory depression, coma
and collapse
.
Concomitant use of alcohol and oxazepam (as well as other benzodiazepines) also increases the risk of an addiction
.
, oxazepam, nitrazepam
, and flunitrazepam
, accounted for the largest volume of forged drug prescriptions in Sweden 1982-1986. During this time, a total of 52% of drug forgeries were for benzodiazepines, suggesting benzodiazepines were a major prescription drug class of abuse.
However, due to its slow rate of absorption (the slowest of all benzodiazepines) and its slow onset of action, oxazepam has a relatively low potential for abuse compared to some other benzodiazepines like temazepam
, flunitrazepam
, or triazolam
, which have a high potential for abuse that is similar to barbiturate abuse potential.
.
, and which reminiscents the Polonovski reaction, giving 7-chloro-1,3-dihydro-3-acetoxy-5-phenyl-2H-benzodiazepin-2-one. Subsequent hydrolysis of the product's acetyl group gives oxazepam.
(Group 2b) by the IARC
.
Benzodiazepine
A benzodiazepine is a psychoactive drug whose core chemical structure is the fusion of a benzene ring and a diazepine ring...
derivative. Oxazepam is a benzodiazepine used extensively since the 1960s for the treatment of anxiety and insomnia and in the control of symptoms of alcohol withdrawal. It is a metabolite of diazepam
Diazepam
Diazepam , first marketed as Valium by Hoffmann-La Roche is a benzodiazepine drug. Diazepam is also marketed in Australia as Antenex. It is commonly used for treating anxiety, insomnia, seizures including status epilepticus, muscle spasms , restless legs syndrome, alcohol withdrawal,...
, prazepam
Prazepam
Prazepam is a benzodiazepine derivative drug developed by Warner-Lambert in the 1960s. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Prazepam is a prodrug for desmethyldiazepam which is an active metabolite of prazepam...
and temazepam
Temazepam
Temazepam is an intermediate-acting 3-hydroxy benzodiazepine. It is mostly prescribed for the short-term treatment of sleeplessness in patients who have difficulty maintaining sleep...
. Oxazepam has moderate amnesic, anxiolytic
Anxiolytic
An anxiolytic is a drug used for the treatment of anxiety, and its related psychological and physical symptoms...
, anticonvulsant
Anticonvulsant
The anticonvulsants are a diverse group of pharmaceuticals used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder, since many seem to act as mood stabilizers, and in the treatment of neuropathic pain. The goal of an...
, hypnotic
Hypnotic
Hypnotic drugs are a class of psychoactives whose primary function is to induce sleep and to be used in the treatment of insomnia and in surgical anesthesia...
, sedative
Sedative
A sedative or tranquilizer is a substance that induces sedation by reducing irritability or excitement....
and skeletal muscle relaxant properties compared to other benzodiazepines.
Indications
It is an intermediate acting benzodiazepine with a slow onset of action, so it is usually prescribed to individuals who have trouble staying asleep, rather than falling asleep. It is commonly prescribed for anxiety disorders with associated tension, irritability, and agitation. It is also prescribed for drug and alcohol withdrawal, and for anxiety associated with depressionClinical depression
Major depressive disorder is a mental disorder characterized by an all-encompassing low mood accompanied by low self-esteem, and by loss of interest or pleasure in normally enjoyable activities...
. Physicians may use Oxazepam outside its approved indications to treat social phobia
Social anxiety disorder
Social anxiety disorder , also known as social phobia, is an anxiety disorder characterized by intense fear in social situations causing considerable distress and impaired ability to function in at least some parts of daily life...
, posttraumatic stress disorder, insomnia
Insomnia
Insomnia is most often defined by an individual's report of sleeping difficulties. While the term is sometimes used in sleep literature to describe a disorder demonstrated by polysomnographic evidence of disturbed sleep, insomnia is often defined as a positive response to either of two questions:...
, premenstrual syndrome, and other conditions.
Dosage
- Mild/moderate anxiety - 10 to 15 mg, 3 to 4 times daily
- Severe anxiety - 15 to 30 mg, 3 to 4 times daily
- Symptoms related to alcohol withdrawal - 15 to 30 mg, 3 to 4 times daily
Availability
In the United Kingdom, oxazepam is available generically in the form of 10 mg, 15 mg and 30 mg tablets.In Finland, oxazepam is available generically in the form of 15 mg, 30 mg and 50 mg tablets.
In France, oxazepam is available in the form of 10 mg and 50 mg tablets.
In Australia, oxazepam is available in the form of 5 mg, 7.5 mg, 10 mg, 15 mg and 30 mg tablets.
Usage
Oxazepam along with diazepam, nitrazepam and temazepam, were the four benzodiazepines listed on the pharmaceutical benefits scheme and represented 82% of the benzodiazepine prescriptions in Australia in 1990-1991.Side effects
The side effects of oxazepam are similar in nature to those of other benzodiazepines and may include dizziness, drowsiness, headache, memory impairment, paradoxical excitementParadoxical reaction
A paradoxical reaction or paradoxical effect is when medical treatment, usually a drug, has the opposite effect to that which would normally be expected.An example of a paradoxical reaction is when a pain relief medication causes an increase in pain...
, retrograde amnesia, but does not affect transient global amnesia
Transient global amnesia
Transient global amnesia is a syndrome in clinical neurology whose key defining characteristic is temporary but almost total disruption of short-term memory with a range of problems accessing older memories...
. Side effects due to rapid decrease in dose or abrupt withdrawal from oxazepam may include abdominal and muscle cramps, convulsions, depression, inability to fall asleep or stay asleep, sweating, tremors, or vomiting.
Contraindications
Oxazepam is contraindicated in Myasthenia gravisMyasthenia gravis
Myasthenia gravis is an autoimmune neuromuscular disease leading to fluctuating muscle weakness and fatiguability...
, chronic obstructive pulmonary disease
Chronic obstructive pulmonary disease
Chronic obstructive pulmonary disease , also known as chronic obstructive lung disease , chronic obstructive airway disease , chronic airflow limitation and chronic obstructive respiratory disease , is the co-occurrence of chronic bronchitis and emphysema, a pair of commonly co-existing diseases...
and limited pulmonary reserve, as well as severe hepatic disease.
Special precautions
Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol- or drug-dependent individuals and individuals with comorbid psychiatric disorders. Benzodiazepines including oxazepam are lipophilic drugs and rapidly penetrate membranes and therefore rapidly cross over into the placenta with significant uptake of the drug. Use of benzodiazepines in late pregnancy especially high doses may result in floppy infant syndrome.Pregnancy
Oxazepam when taken during late in pregnancy, the third trimester, causes a definite risk to the neonate including a severe benzodiazepine withdrawal syndromeBenzodiazepine withdrawal syndrome
Benzodiazepine withdrawal syndrome—often abbreviated to benzo withdrawal—is the cluster of symptoms which appear when a person who has taken benzodiazepines long term and has developed benzodiazepine dependence stops taking benzodiazepine drug or during dosage reductions...
in the neonate with symptoms including hypotonia
Hypotonia
Hypotonia is a state of low muscle tone , often involving reduced muscle strength. Hypotonia is not a specific medical disorder, but a potential manifestation of many different diseases and disorders that affect motor nerve control by the brain or muscle strength...
, and reluctance to suck, to apnoeic spells, cyanosis
Cyanosis
Cyanosis is the appearance of a blue or purple coloration of the skin or mucous membranes due to the tissues near the skin surface being low on oxygen. The onset of cyanosis is 2.5 g/dL of deoxyhemoglobin. The bluish color is more readily apparent in those with high hemoglobin counts than it is...
, and impaired metabolic responses to cold stress. Floppy infant syndrome and sedation in the new born may also occur. Symptoms of floppy infant syndrome and the neonatal benzodiazepine withdrawal syndrome have been reported to persist from hours to months after birth.
Tolerance, dependence and withdrawal
Oxazepam as with other benzodiazepineBenzodiazepine
A benzodiazepine is a psychoactive drug whose core chemical structure is the fusion of a benzene ring and a diazepine ring...
drugs can cause tolerance, physical dependence
Physical dependence
Physical dependence refers to a state resulting from chronic use of a drug that has produced tolerance and where negative physical symptoms of withdrawal result from abrupt discontinuation or dosage reduction...
, addiction
Substance dependence
The section about substance dependence in the Diagnostic and Statistical Manual of Mental Disorders does not use the word addiction at all. It explains:...
and what is known as the benzodiazepine withdrawal syndrome
Benzodiazepine withdrawal syndrome
Benzodiazepine withdrawal syndrome—often abbreviated to benzo withdrawal—is the cluster of symptoms which appear when a person who has taken benzodiazepines long term and has developed benzodiazepine dependence stops taking benzodiazepine drug or during dosage reductions...
. Withdrawal from oxazepam or other benzodiazepines often leads to withdrawal symptoms which are similar to those seen during alcohol and barbiturate
Barbiturate
Barbiturates are drugs that act as central nervous system depressants, and can therefore produce a wide spectrum of effects, from mild sedation to total anesthesia. They are also effective as anxiolytics, as hypnotics, and as anticonvulsants...
withdrawal. The higher the dose and the longer the drug is taken the greater the risk of experiencing unpleasant withdrawal symptoms. Withdrawal symptoms can however occur at standard dosages and also after short term use. Benzodiazepine treatment should be discontinued as soon as possible via a slow and gradual dose reduction regimen.
Pharmacology
Oxazepam is an intermediate acting benzodiazepine of the 3-hydroxy family. Oxazepam acts on benzodiazepine receptors resulting in increased effect of GABAGamma-aminobutyric acid
γ-Aminobutyric acid is the chief inhibitory neurotransmitter in the mammalian central nervous system. It plays a role in regulating neuronal excitability throughout the nervous system...
to the GABAA receptor which results in inhibitory effects on the central nervous system
Central nervous system
The central nervous system is the part of the nervous system that integrates the information that it receives from, and coordinates the activity of, all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish...
. The half-life
Biological half-life
The biological half-life or elimination half-life of a substance is the time it takes for a substance to lose half of its pharmacologic, physiologic, or radiologic activity, as per the MeSH definition...
of oxazepam is 4–15 hours. Oxazepam has been shown to suppress cortisol
Cortisol
Cortisol is a steroid hormone, more specifically a glucocorticoid, produced by the adrenal gland. It is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat,...
levels. Oxazepam is the most slowly absorbed benzodiazepine and has the slowest onset of action of all the common benzodiazepines according to one British study.
Oxazepam is an active metabolite formed during the breakdown of diazepam
Diazepam
Diazepam , first marketed as Valium by Hoffmann-La Roche is a benzodiazepine drug. Diazepam is also marketed in Australia as Antenex. It is commonly used for treating anxiety, insomnia, seizures including status epilepticus, muscle spasms , restless legs syndrome, alcohol withdrawal,...
, nordazepam
Nordazepam
Nordazepam , also known as desoxydemoxepam, nordiazepam and desmethyldiazepam, is a 1,4-benzodiazepine derivative. Like other benzodiazepine derivatives, it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties...
, and certain similar drugs. Oxazepam may be safer than many other benzodiazepines in patients with impaired liver function because it does not require hepatic oxidation, but rather it is simply metabolized via glucuronidation
Glucuronidation
Glucuronidation is the addition of glucuronic acid to a substrate. Glucuronidation is often involved in xenobiotic metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids...
. This means that oxazepam is less likely to accumulate and cause adverse reactions in the elderly or people with liver disease. Oxazepam is similar to lorazepam
Lorazepam
Lorazepam is a high-potency short-to-intermediate-acting 3-hydroxy benzodiazepine drug that has all five intrinsic benzodiazepine effects: anxiolytic, amnesic, sedative/hypnotic, anticonvulsant, antiemetic and muscle relaxant...
in this respect. (1)
There is preferential storage of oxazepam in some organs including the heart of the neonate. Absorption by any administered route and the risk of accumulation is significantly increased in the neonate and it is recommended to withdraw oxazepam during pregnancy and breast feeding as oxazepam is excreted in breast milk.
Interactions
As oxazepam is an active metabolite of diazepamDiazepam
Diazepam , first marketed as Valium by Hoffmann-La Roche is a benzodiazepine drug. Diazepam is also marketed in Australia as Antenex. It is commonly used for treating anxiety, insomnia, seizures including status epilepticus, muscle spasms , restless legs syndrome, alcohol withdrawal,...
, there is likely an overlap in possible interactions with other drugs or food, with exception of the pharmacokinetic CYP450 interactions (e.g. with cimetidine
Cimetidine
Cimetidine INN is a histamine H2-receptor antagonist that inhibits the production of acid in the stomach. It is largely used in the treatment of heartburn and peptic ulcers. It is marketed by GlaxoSmithKline under the trade name Tagamet...
). Take precautions, and follow closely the prescription of your doctor, when taking oxazepam (or other benozodiazepines) in combinations with antidepressant medication (SSRI
Selective serotonin reuptake inhibitor
Selective serotonin re-uptake inhibitors or serotonin-specific reuptake inhibitor are a class of compounds typically used as antidepressants in the treatment of depression, anxiety disorders, and some personality disorders. The efficacy of SSRIs is disputed...
s such as Prozac, Zoloft, and Paxil, or multiple reuptake inhibitors such as Wellbutrin, Cymbalta, or Effexor), potent painkillers
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
(opioids, e.g. morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
, oxycodone
Oxycodone
Oxycodone is an opioid analgesic medication synthesized from opium-derived thebaine. It was developed in 1916 in Germany, as one of several new semi-synthetic opioids in an attempt to improve on the existing opioids: morphine, diacetylmorphine , and codeine.Oxycodone oral medications are generally...
or methadone
Methadone
Methadone is a synthetic opioid, used medically as an analgesic and a maintenance anti-addictive for use in patients with opioid dependency. It was developed in Germany in 1937...
). Concurrent use of these medicines (as well as other benzodiazepine
Benzodiazepine
A benzodiazepine is a psychoactive drug whose core chemical structure is the fusion of a benzene ring and a diazepine ring...
s) can interact in a way that is difficult to predict. Drinking alcohol when taking oxazepam is not recommended. Concomitant use of oxazepam and alcohol can lead to increased sedation
Sedation
Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure...
, severe problems with coordination
Motor coordination
thumb|right|Motor coordination is shown in this animated sequence by [[Eadweard Muybridge]] of himself throwing a diskMotor coordination is the combination of body movements created with the kinematic and kinetic parameters that result in intended actions. Such movements usually smoothly and...
(ataxia
Ataxia
Ataxia is a neurological sign and symptom that consists of gross lack of coordination of muscle movements. Ataxia is a non-specific clinical manifestation implying dysfunction of the parts of the nervous system that coordinate movement, such as the cerebellum...
e), decreased muscle tone and in severe cases or in predisposed patients even to life-threatening intoxications with respiratory depression, coma
Coma
In medicine, a coma is a state of unconsciousness, lasting more than 6 hours in which a person cannot be awakened, fails to respond normally to painful stimuli, light or sound, lacks a normal sleep-wake cycle and does not initiate voluntary actions. A person in a state of coma is described as...
and collapse
Collapse (medical)
Collapse is a sudden and often unannounced loss of postural tone , often but not necessarily accompanied by loss of consciousness.If the episode was accompanied by a loss of consciousness, the term syncope is used. The main causes are cardiac , seizures or a psychological cause...
.
Concomitant use of alcohol and oxazepam (as well as other benzodiazepines) also increases the risk of an addiction
Substance dependence
The section about substance dependence in the Diagnostic and Statistical Manual of Mental Disorders does not use the word addiction at all. It explains:...
.
Overdose
Oxazepam is generally less toxic in overdose than other benzodiazepines. Important factors which effect the severity of a benzodiazepine overdose include the dose ingested, the age of the patient, health status prior to overdose. Benzodiazepine overdoses can be much more dangerous if there has been a coingestion of other CNS depressants such as opiates or alcohol. Symptoms of an oxazepam overdose include:- Respiratory depression
- Excessive somnolenceSomnolenceSomnolence is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods . It has two distinct meanings, referring both to the usual state preceding falling asleep, and the chronic condition referring to being in that state independent of a circadian rhythm...
- Altered consciousnessConsciousnessConsciousness is a term that refers to the relationship between the mind and the world with which it interacts. It has been defined as: subjectivity, awareness, the ability to experience or to feel, wakefulness, having a sense of selfhood, and the executive control system of the mind...
- Central nervous system depression
- Occasionally cardiovascular and pulmonary toxicityPulmonary toxicityPulmonary toxicity is the medical name for side effects on the lungs.Although most cases of pulmonary toxicity in medicine are due to side effects of medicinal drugs, many cases can be due to side effects of radiation...
- Rarely deep comaComaIn medicine, a coma is a state of unconsciousness, lasting more than 6 hours in which a person cannot be awakened, fails to respond normally to painful stimuli, light or sound, lacks a normal sleep-wake cycle and does not initiate voluntary actions. A person in a state of coma is described as...
Abuse
Oxazepam is a drug with the potential for misuse. Drug misuse is defined as taking the drug to achieve a high, or continuing to take the drug in the long term against medical advice. Benzodiazepines, including diazepamDiazepam
Diazepam , first marketed as Valium by Hoffmann-La Roche is a benzodiazepine drug. Diazepam is also marketed in Australia as Antenex. It is commonly used for treating anxiety, insomnia, seizures including status epilepticus, muscle spasms , restless legs syndrome, alcohol withdrawal,...
, oxazepam, nitrazepam
Nitrazepam
Nitrazepam is a type of benzodiazepine drug and is marketed in English-speaking countries under the following brand names: Alodorm, Arem, Insoma, Mogadon, Nitrados, Nitrazadon, Ormodon, Paxadorm, Remnos, and Somnite...
, and flunitrazepam
Flunitrazepam
Flunitrazepam is marketed as a potent hypnotic, sedative, anticonvulsant, anxiolytic, amnestic, and skeletal muscle relaxant drug most commonly known as Rohypnol...
, accounted for the largest volume of forged drug prescriptions in Sweden 1982-1986. During this time, a total of 52% of drug forgeries were for benzodiazepines, suggesting benzodiazepines were a major prescription drug class of abuse.
However, due to its slow rate of absorption (the slowest of all benzodiazepines) and its slow onset of action, oxazepam has a relatively low potential for abuse compared to some other benzodiazepines like temazepam
Temazepam
Temazepam is an intermediate-acting 3-hydroxy benzodiazepine. It is mostly prescribed for the short-term treatment of sleeplessness in patients who have difficulty maintaining sleep...
, flunitrazepam
Flunitrazepam
Flunitrazepam is marketed as a potent hypnotic, sedative, anticonvulsant, anxiolytic, amnestic, and skeletal muscle relaxant drug most commonly known as Rohypnol...
, or triazolam
Triazolam
Triazolam is a benzodiazepine drug. It possesses pharmacological properties similar to that of other benzodiazepines, but it is generally only used as a sedative to treat severe insomnia...
, which have a high potential for abuse that is similar to barbiturate abuse potential.
Legal status
Oxazepam is a Schedule IV drug under the Convention on Psychotropic SubstancesConvention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...
.
Chemistry
6-Chloro-2-chloromethyl-4-phenylquinazolin-3-oxide undergoes treatment with sodium hydroxide, giving 7-chloro-5-phenyl-1,2-dihydro-3H-1,4-benzodiazepin-2-on-4-oxide. This undergoes an acetoxylation reaction of the third position of the benzodiazepine ring, using acetic anhydrideAcetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula 2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis...
, and which reminiscents the Polonovski reaction, giving 7-chloro-1,3-dihydro-3-acetoxy-5-phenyl-2H-benzodiazepin-2-one. Subsequent hydrolysis of the product's acetyl group gives oxazepam.
Carcinogenicity
Oxazepam is listed as a possible carcinogenCarcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
(Group 2b) by the IARC
International Agency for Research on Cancer
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organisation of the United Nations....
.
See also
- BenzodiazepineBenzodiazepineA benzodiazepine is a psychoactive drug whose core chemical structure is the fusion of a benzene ring and a diazepine ring...
- Benzodiazepine dependenceBenzodiazepine dependenceBenzodiazepine dependence or benzodiazepine addiction is a condition during which a person is dependent on benzodiazepine drugs. Dependence can be either a psychological dependence, physical dependence, or a combination of the two...
- Benzodiazepine withdrawal syndromeBenzodiazepine withdrawal syndromeBenzodiazepine withdrawal syndrome—often abbreviated to benzo withdrawal—is the cluster of symptoms which appear when a person who has taken benzodiazepines long term and has developed benzodiazepine dependence stops taking benzodiazepine drug or during dosage reductions...
- Long-term effects of benzodiazepines