7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 720
• Molecular Formular: C15H11ClN2O2
• Molecular Mass: 286.71304
• Monoisotopic Mass: 286.05090528
• SMILES: Clc1cc2C(=NC(O)C(=O)Nc2cc1)c1ccccc1
• Canonical SMILES: O=C1Nc2ccc(cc2C(=NC1O)c1ccccc1)Cl
• InChI: InChI=1S/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)
• InChIKey: ADIMAYPTOBDMTL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: oxazepam
• Brand Name: Adumbran; Ansioxacepam; Anxiolit; Aplakil; Astress; Azutranquil; Bonare; Drimuel; Droxacepam; Durazepam; Enidrel; Hi-Long; Isodin; Lederpam; Limbial; Murelax; Nesontil; Noctazepam; Notaral; Oxa-puren; Oxanid; Pacienx; Praxiten; Propax; Psiquiwas; QUEN; Quilibrex; Rondar; Sedigoa; Serax; Serenal; Serenid; Serenid-D; Serepax; Seresta; Serpax; Sigacalm; Sobril; Tacepam; Tazepam; Uskan; Vaben; Wy-3498 stic; Zaxopam
• Synonyms: 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Adumbran; Anxiolit; Durazepam; N-Desmethyltemazepam; NSC 169448; Nesontil; Noctazepam; Serepax; Seresta; Wy 3498; Zaxopam; d-Oxazepam hemisuccinate; Oxozepam; Oxazipam; Oxazepam; 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-1,4(2H)-benzodiazepin-2-one; Oxazepam

Database IDs

• CAS Number: 604-75-1
• EC Number: 210-076-9
• MDL Number: MFCD00057903
• PubChem SID: 160964183; 46506031; 24898014
• PubChem CID: 4616
• CHEBI ID: 7823
• ATC CODE: N05BA04
• CHEMBL: 568
• Chemspider ID: 4455
• DrugBank ID: DB00842
• KEGG ID: D00464
• MeSH Name: Oxazepam
• Unique Ingredient Identifier: 6GOW6DWN2A
• Wikipedia Title: Oxazepam

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.607201
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.9232774
• LogD (pH = 7.4): 2.9230137
• Log P: 2.9232807
• Molar Refractivity: 77.8944 cm^3
• Polarizability: 29.113512 Å^3
• Polar Surface Area: 61.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.01
• LOG S: -3.51
• Solubility (Water): 8.81e-02 g/l

PROPERTIES

Physical Property

• Solubility: 179 mg L^-1 in water; 179 mg/L
• Melting Point: 205 - 206°C
• Partition Coefficient: 2.216
• Hydrophobicity(logP): 2.8
• pKa: 10.939
• pKb: 3.058

Safety Information

• RTECS: DF1400000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40; R40
• Safety Statements: 36/37; S36/37
• GHS Pictograms: GHS health hazard; GHS08
• GHS Signal Word: WARNING; Warning
• GHS Hazard statements: 351; H351
• GHS Precautionary statements: 281; P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 95.5%
• Excretion: Renal
• Half Life: 5-15 h
• Metabolism: Hepatic
• Legal Status: S4 (Australia); Schedule IV (US)
• Gene Information: human ... GABRA1(2554)

DETAILS

DrugBank - DB00842

• Drug Groups: approved
• Description: Oxazepam is an intermediate-acting benzodiazepine used to treat alcohol withdrawal and anxiety disorders.
• Indication: For the treatment of anxiety disorders and alcohol withdrawal.
• Pharmacology: Oxazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.
• Toxicity: Symptoms of overdose include confusion, drowsiness, and lethargy.
• Affected Organisms: Humans and other mammals
• Biotransformation: No active metabolites. Metabolized via conjugation prior to elimination.
• Absorption: Well absorbed from the gastrointestinal tract following oral administration. Time to peak concentration = 2-4 hours. Onset of action is slow, > 3 hours, following oral administration.
• Half Life: 5-15 hours
• Protein Binding: 80-99%
• Elimination: This product has a single, major inactive metabolite in man, a glucuronide excreted in the urine.
• References: Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. [Pubmed] ; Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [Pubmed] ; Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; Christensen P, Lolk A, Gram LF, Kragh-Sorensen P: Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers. Psychopharmacology (Berl). 1992;106(4):511-6. [Pubmed] ; Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - O5254

Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

Toronto Research Chemicals - O845700

Anxiolytic; muscle relaxant (skeletal); anticonvulsant; ligand for the GABAA receptor benzodiazepine modulatory site. Controlled substance (depressant).

REFERENCES

• Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. Pubmed
• Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. Pubmed
• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• Christensen P, Lolk A, Gram LF, Kragh-Sorensen P: Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers. Psychopharmacology (Berl). 1992;106(4):511-6. Pubmed
• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. Pubmed
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Sisenwine, et al.: Arzneim. Forsch., 22, 682 (1971)
• Shearer, C.M., et al.: Anal. Profiles Drug Subs., 3, 441 (1971)
• Greenblatt, D.J., et al.: Clin. Pharmacokinet., 6, 89 (1971)