604-75-1 Usage
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
Different sources of media describe the General Description of 604-75-1 differently. You can refer to the following data:
1. 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.
2. 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.
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).
Process for catalyzing the oxidation of organic compounds
-
Page column 6-8, (2008/06/13)
Oxidation of organic compounds is catalyzed by addition of a catalytic amount of a metalloporphyrin in a non-reactive aprotic solvent.