OXAZEPAM

OXAZEPAM Basic information
Product Name:OXAZEPAM
Synonyms:2h-1,4-benzodiazepin-2-one,7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-[qr];7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one;7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-2h-1,4-benzodiazepin-2-one[qr];7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepine-2-one;7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-2h-1,4-benzodiazepine-2-one[qr];7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-2h-4-benzodiazepin-2-one;7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one;7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one[qr]
CAS:604-75-1
MF:C15H11ClN2O2
MW:286.71
EINECS:210-076-9
Product Categories:Aromatics;Heterocycles;API;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:604-75-1.mol
OXAZEPAM Structure
OXAZEPAM Chemical Properties
Melting point 205-206°
Boiling point 506.5±50.0 °C(Predicted)
density 1.3052 (rough estimate)
refractive index 1.5200 (estimate)
Fp 11 °C
storage temp. −20°C
solubility Practically insoluble in water, slightly soluble in ethanol (96 per cent).
form neat
pkapKa 1.6/11.6(5% MeOH in H2O,t =20,I=0.15) (Uncertain)
Water Solubility 20mg/L(22 ºC)
CAS DataBase Reference604-75-1(CAS DataBase Reference)
IARC2B (Vol. Sup 7, 66) 1996
EPA Substance Registry SystemOxazepam (604-75-1)
Safety Information
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 Data604-75-1(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): >5010, >5010 orally (Goldenthal)
MSDS Information
ProviderLanguage
SigmaAldrich English
OXAZEPAM Usage And Synthesis
Chemical PropertiesOff-White Solid
OriginatorSerax,Wyeth,US,1965
UsesAnxiolytic; muscle relaxant (skeletal); anticonvulsant; ligand for the GABAA receptor benzodiazepine modulatory site. Controlled substance (depressant).
DefinitionChEBI: 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 nameSerax (Alpharma); Zaxopam (Quantum Pharmics).
Therapeutic FunctionTranquilizer
General DescriptionOxazepam, 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 DescriptionOdorless creamy-white to pale-yellow powder or white crystalline solid. Bitter taste. pH (2% aqueous suspension) 4.8-7.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileOXAZEPAM is stable in light and is non hygroscopic. OXAZEPAM is stable in neutral solution. OXAZEPAM is hydrolyzed by acids and bases.
Fire HazardFlash point data for OXAZEPAM are not available; however, OXAZEPAM is probably combustible.
PharmacokineticsThe 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 UseOxazepam
Drug interactionsPotentially 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.
MetabolismOxazepam 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
Raw materialsSodium hydroxide-->Acetic anhydride
(R)-Lorazepam LORAZEPAM-D4 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one 3-hydroxyhalazepam 3-(Acetyloxy)-7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one camazepam oxazepam glucuronide oxazepam-d5solution,oxazepam-D5 100 ug per ml in methanol,oxazepam-phenyl-D5--dea schedule*iv item,OXAZEPAM-D5 Pivoxazepam (S)-Lorazepam 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one temazepam glucuronide LORMETAZEPAM TEMAZEPAM-D5 Doxefazepam Cinolazepam TEMAZEPAM Lorazepam

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