OXAZEPAM Property

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)

IARC

2B (Vol. Sup 7, 66) 1996

EPA Substance Registry System

Oxazepam (604-75-1)

Safety

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

Hazardous Substances Data

604-75-1(Hazardous Substances Data)

Toxicity

LD50 in mice, rats (mg/kg): >5010, >5010 orally (Goldenthal)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H336May cause drowsiness or dizziness

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

OXAZEPAM Chemical Properties,Usage,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

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.

General Description

Odorless creamy-white to pale-yellow powder or white crystalline solid. Bitter taste. pH (2% aqueous suspension) 4.8-7.

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.