604-75-1

Basic information

• Product Name: OXAZEPAM
• Synonyms: 1,3-dihydro-7-chloro-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-;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
• CAS NO: 604-75-1
• Molecular Formula: C₁₅H₁₁ClN₂O₂
• Molecular Weight: 286.71
• EINECS: 210-076-9
• Product Categories: API;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;+8618031153937;Oxazepam ada@tuskwei.com whatsapp
• Mol File: 604-75-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 205-206°
• Boiling Point: 506.5oC at 760 mmHg
• Flash Point: 11 °C
• Appearance: /
• Density: 1.3052 (rough estimate)
• Vapor Pressure: 4.4E-11mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• 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: OXAZEPAM(CAS DataBase Reference)
• NIST Chemistry Reference: OXAZEPAM(604-75-1)
• EPA Substance Registry System: OXAZEPAM(604-75-1)

Safety Data

• Hazard Codes: Xn,T,F
• 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
• Hazardous Substances Data: 604-75-1(Hazardous Substances Data)

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.

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

Upstream product

• 1824-74-4 d-oxazepam acetate 
• 1824-74-4 l-oxazepam acetate 
• 439-14-5 diazepam 
• 963-39-3 demoxepam 
• 2888-63-3 2-Chloracetamino-5-chlor-benzophenon-α-oxim 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 4016-85-7 5-chloro-2-(chloroacetylamino)benzophenone 
• 1824-74-4 d-oxazepam acetate 
• 1824-74-4 l-oxazepam acetate 
• 68398-12-9 oxazepam diethylacetate 
• 604-75-1 (+)-Oxazepam 
• 604-75-1 (-)-Oxazepam 
• 18097-52-4 2-amino-5-chlorobenzophenone oxime 
• 17977-76-3 2-chloro-N-{4-chloro-2-[(hydroxyimino)(phenyl)methyl]phenyl}acetamide 

Downstream Products

• 3967-08-6 3-morpholino-7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one 
• 604-75-1 (-)-Oxazepam 
• 604-75-1 (+)-Oxazepam 
• 18878-19-8 3-O-methyloxazepam 
• 91254-23-8 7-Chloro-3-hydroxy-1-hydroxymethyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 4951-07-9 3-O-ethyloxazepam 
• 67-56-1 methanol 
• 130753-94-5 2-Methyl-3-nitro-benzoic acid 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl ester 
• 128014-58-4 9H-β-Carboline-3-carboxylic acid 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl ester 
• 71107-56-7 oxazepam β-phenyl-propionate 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 5958-05-4 6-chloro 4-phenyl quinazoline 2 carboxaldehyde 
• 60628-57-1 3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one 
• 91403-22-4 7-chloro-3-diethylamino-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 

Relevant articles and documents

Oxazepam-Dopamine Conjugates Increase Dopamine Delivery into Striatum of Intact Rats

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

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

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.