OXAZEPAM
- CAS No.
- 604-75-1
- Chemical Name:
- OXAZEPAM
- Synonyms
- Oxazepine;Serax;Zaxopam;7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one;2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-;QUEN;Uskan;Vaben;Bonare;Isodin
- CBNumber:
- CB6444321
- Molecular Formula:
- C15H11ClN2O2
- Molecular Weight:
- 286.71
- MDL Number:
- MFCD00057903
- MOL File:
- 604-75-1.mol
| Melting point | 205-206° |
|---|---|
| Boiling point | 506.5±50.0 °C(Predicted) |
| Density | 1.3052 (rough estimate) |
| refractive index | 1.5200 (estimate) |
| Flash point | 11 °C |
| storage temp. | −20°C |
| solubility | Practically insoluble in water, slightly soluble in ethanol (96 per cent). |
| pka | pKa 1.6/11.6(5% MeOH in H2O,t =20,I=0.15) (Uncertain) |
| Water Solubility | 20mg/L(22 ºC) |
| CAS DataBase Reference | 604-75-1(CAS DataBase Reference) |
| EWG's Food Scores | 2 |
| FDA UNII | 6GOW6DWN2A |
| IARC | 2B (Vol. Sup 7, 66) 1996 |
| Proposition 65 List | Oxazepam |
| ATC code | N05BA04 |
| EPA Substance Registry System | Oxazepam (604-75-1) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H336-H351 | |||||||||
| Precautionary statements | P202-P261-P271-P280-P304+P340+P312-P308+P313 | |||||||||
| Hazard Codes | Xn,T,F | |||||||||
| Risk Statements | 40-39/23/24/25-23/24/25-11 | |||||||||
| Safety Statements | 7-16-36/37-45 | |||||||||
| RIDADR | UN 1230 3/PG 2 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | DF1400000 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 2933910000 | |||||||||
| Toxicity | LD50 in mice, rats (mg/kg): >5010, >5010 orally (Goldenthal) | |||||||||
| NFPA 704 |
|
OXAZEPAM Chemical Properties,Uses,Production
Chemical Properties
Off-White Solid
Originator
Serax,Wyeth,US,1965
Uses
Anxiolytic; muscle relaxant (skeletal); anticonvulsant; ligand for the GABAA receptor benzodiazepine modulatory site. Controlled substance (depressant).
Definition
ChEBI: A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.
Manufacturing Process
(A) Suspend 10 g of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2one 4-oxide in 150 ml of acetic anhydride and warm on a steam bath with stirring until all the solid has dissolved. Cool and filter off crystalline, analytically pure 3-acetoxy-7-chloro-1,3-dihydro-5-phenyl-2H-1,4benzodiazepin-2-one, melting point 242°C to 243°C.
(B) Add to a suspension of 3.4 g of 3-acetoxy-7-chloro-1,3-dihydro-5-phenyl2H-1,4-benzodiazepin-2-one in 80 ml of alcohol.6 ml of 4 N sodium hydroxide. Allow to stand after complete solution takes place to precipitate a solid. Redissolve the solid by the addition of 80 ml of water. Acidify the solution with acetic acid to give white crystals. Recrystallize from ethanol to obtain 7chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, melting point 203°C to 204°C.
brand name
Serax (Alpharma); Zaxopam (Quantum Pharmics).
Therapeutic Function
Tranquilizer
General Description
Odorless creamy-white to pale-yellow powder or white crystalline solid. Bitter taste. pH (2% aqueous suspension) 4.8-7.
General Description
Oxazepam, 7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazpin-2-one (Serax), isan active metabolite of both chlordiazepoxide and diazepamand can be considered a prototype for the 3-hydroxy benzo-diazepines. It is much more polar than diazepam. Oxazepam is rapidlyinactivated to glucuronidated metabolites that are excretedin the urine. Thus, the half-life of oxazepam is about 4 to 8hours, and it is marketed as a short-acting anxiolytic. As aresult, its cumulative effects with chronic therapy are muchless than with long-acting benzodiazepine such as chlordiazepoxideand diazepam.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
OXAZEPAM is stable in light and is non hygroscopic. OXAZEPAM is stable in neutral solution. OXAZEPAM is hydrolyzed by acids and bases.
Fire Hazard
Flash point data for OXAZEPAM are not available; however, OXAZEPAM is probably combustible.
Pharmacokinetics
The half-life of oxazepam is approximately 4 to 8 hours, and cumulative effects with chronic therapy are much less than with long-acting benzodiazepines, such as chlordiazepoxide and diazepam. Lorazepam is the 2′-chloro derivative of oxazepam and has a similarly short half-life (2–6 hours) and pharmacological activity.
Clinical Use
Oxazepam
Drug interactions
Potentially hazardous interactions with other drugs
Antibacterials: metabolism possibly increased by
rifampicin.
Antipsychotics: enhanced sedative effects; risk of
serious adverse effects in combination with clozapine.
Antivirals: possibly increased concentration with
ritonavir.
Sodium oxybate: enhanced effects of sodium oxybate
- avoid.
Ulcer-healing drugs: metabolism inhibited by
cimetidine.
Metabolism
Oxazepam is an active metabolite of both chlordiazepoxide and diazepam and is marketed separately, as a shortacting anxiolytic agent. Oxazepam is rapidly inactivated to glucuronidated metabolites that are excreted in the urine.
OXAZEPAM Preparation Products And Raw materials
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