Oxazepam

• IUPAC: (RS)- 7-chloro -3-hydroxy -5-phenyl -2 ,3- dihydro-1H- 1,4- benzodiazepin- 2-one
• (±)- 7-chloro -3-hydroxy -5-phenyl -2 ,3- dihydro-1H- 1,4- benzodiazepin- 2-one
• Rac- 7-chloro -3-hydroxy -5-phenyl -2 ,3- dihydro-1H- 1,4- benzodiazepin- 2-one
• Latin: Oxazepamum

N05BA04

White to off- white crystalline powder

Benzodiazepines, anxiolytics

205-206 ° C

• Water: 179 mg · l-1 (25 ° C)
• Readily soluble in dioxane, sparingly soluble in dichloromethane and ethanol

Attention

1540 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Oxazepam is a drug of the benzodiazepine group with moderately long duration of action. The indications, contraindications, side effects and interactions are similar to those of all benzodiazepines. Oxazepam was established in 1965 by Dr. Karl Thomae GmbH (now Boehringer Ingelheim) on the market. It can lead to psychological and physical dependence after a short application.

Pharmacology

Oxazepam is a pharmacologically active metabolite of diazepam and itself forms no active metabolites more. Onset of action occurs in oxazepam slower than most other benzodiazepines, making it somewhat less suitable for acute situations as, for example, the similar lorazepam. The duration of action of 8-12 hours. Oxazepam and lorazepam are not degraded via the cytochrome P450 ( CYP2C19 ) and therefore does not change at a CYP2C19 mutation (2-5% of the German population ) their duration of action. This is a significant advantage of these substances compared with other benzodiazepines. Since the metabolism takes place only via a glucuronidation, is itself unlikely to have more advanced liver damage with a significantly prolonged duration of action, which is a further advantage. However, in liver cirrhosis therapy mirror control is useful.

Use in pregnancy and lactation

The use of benzodiazepines during pregnancy may cause unwanted effects in the unborn child. Oxazepam may therefore be used during pregnancy unless clearly necessary. It can cause hypotension, hypothermia, hypoactivity and respiratory depression in the newborn. Withdrawal symptoms may also appear later. In animal models, there is evidence of behavioral problems of the offspring of maternal animals exposed to benzodiazepines were administered.

Isomerism

Oxazepam contains a stereocenter. Consequently, there are two enantiomers, (R) - and (S)- isomer, which bind to serum albumin significantly different.

In the synthesis of the racemate produced oxazepam. The enantiomers are unstable and racemized rapidly in aqueous solution, with ring opening to the tautomeric Iminoaldehyd so that the pharmaceutical use of a pure enantiomer is unnecessary.