604-75-1 Usage
Description
Oxazepam, also known as Serax, is 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 a phenyl group at position 5. It is an active metabolite of both chlordiazepoxide and diazepam and can be considered a prototype for the 3-hydroxy benzodiazepines. Oxazepam is an odorless creamy-white to pale-yellow powder or white crystalline solid with a bitter taste. It is much more polar than diazepam and is rapidly inactivated to glucuronidated metabolites that are excreted in the urine. The half-life of oxazepam is about 4 to 8 hours, and it is marketed as a short-acting anxiolytic.
Uses
Used in Pharmaceutical Industry:
Oxazepam is used as an anxiolytic for the short-term relief of anxiety symptoms. It acts as a muscle relaxant for skeletal muscles, providing relief from muscle spasms and tension. Additionally, it serves as an anticonvulsant, helping to prevent and control seizures. Oxazepam also functions as a ligand for the GABAA receptor benzodiazepine modulatory site, enhancing the effects of GABA and promoting relaxation.
Used in Controlled Substances:
Oxazepam is classified as a controlled substance (depressant) due to its potential for dependency and abuse. It is important to use this medication under the supervision of a healthcare professional and follow the prescribed dosage to minimize the risk of dependency.
Originator
Serax,Wyeth,US,1965
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.
Therapeutic Function
Tranquilizer
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.
Check Digit Verification of cas no
The CAS Registry Mumber 604-75-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 4 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 604-75:
(5*6)+(4*0)+(3*4)+(2*7)+(1*5)=61
61 % 10 = 1
So 604-75-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)/t15-/m1/s1
604-75-1Relevant articles and documents
Oxazepam-Dopamine Conjugates Increase Dopamine Delivery into Striatum of Intact Rats
Cassano, Tommaso,Lopalco, Antonio,De Candia, Modesto,Laquintana, Valentino,Lopedota, Angela,Cutrignelli, Annalisa,Perrone, Mara,Iacobazzi, Rosa M.,Bedse, Gaurav,Franco, Massimo,Denora, Nunzio,Altomare, Cosimo D.
, p. 3178 - 3187 (2017/09/11)
The neurotransmitter dopamine (DA) was covalently linked to oxazepam (OXA), a well-known positive allosteric modulator of γ-aminobutyric acid type-A (GABAA) receptor, through a carbamate linkage (4) or a succinic spacer (6). These conjugates were synthesized with the aim of improving the delivery of DA into the brain and enhancing GABAergic transmission, which may be useful for the long-term treatment of Parkinson disease (PD). Structure-based permeability properties, in vitro stability, and blood-brain barrier (BBB) permeability studies led to identify the OXA-DA carbamate conjugate 4a as the compound better combining sufficient stability and ability to cross BBB. Finally, in vivo microdialysis experiments in freely moving rats demonstrated that 4a (20 mg/kg, i.p.) significantly increases extracellular DA levels into striatum, with a peak (more than 15-fold increase over the baseline) at about 80 min after a single administration. The stability and delivery data proved that 4a may be a promising candidate for further pharmacological studies in animal models of PD.
Efficient synthesis of 3-hydroxy-1,4-benzodiazepines oxazepam and lorazepam by new acetoxylation reaction of 3-position of 1,4-benzodiazepine ring
Cepanec, Ivica,Litvic, Mladen,Pogorelic, Ivan
, p. 1192 - 1198 (2012/12/23)
Simple, efficient, and scalable syntheses of 3-hydroxy-1,4-benzodiazepines, oxazepam (1), and lorazepam (2) were developed. The syntheses are based on the new acetoxylation reaction of the 3-position of the 1,4-benzodiazepine ring. The reaction involves iodine (20-50 mol %)-catalyzed acetoxylation in the presence of potassium acetate (2 equiv) and potassium peroxydisulfate (1-2 equiv) as a stoichiontetric oxidant affording the corresponding 3-acetoxy-1,4- benzodiazepines in good-to-high yields. The latter were converted by selective saponification to 3-hydroxy-1,4-benzodiazepines of very high purity (>99.8%) in an overall yield of 83% (oxazepam) and 64% (lorazepam).
NOVEL 3-SUBSTITUTED-1,4-BENZODIAZEPINES
-
, (2010/02/09)
The present invention relates to compounds of formula (I). The invention also relates to methods for preparing the compounds and their uses as CCK receptor ligands and CCK antagonists.
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