CAS 604-75-1|7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one|oxazepam|7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-1,4(2H)-benzodiazepin-2-one|Oxazepam|Oxanid|Seresta|Oxazepam|Noctazep...

General Information

Structure

Molecular Formula

C₁₅H₁₁ClN₂O₂

Molecular Mass

286.71304

Exact Mass

286.05090528

Charge

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

Canonic Smiles

O=C1Nc2ccc(cc2C(=NC1O)c1ccccc1)Cl

Isomeric Smiles

Clc1cc2C(=NC(O)C(=O)Nc2cc1)c1ccccc1

Calculated Properties

JChem

Acid pKa

10.607201

H Acceptors

H Donor

LogD (pH = 5.5)

2.9232774

LogD (pH = 7.4)

2.9230137

Log P

2.9232807

Molar Refractivity

77.8944

Polarizability

29.113512

Polar Surface Area

61.69

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.01

LOG S

-3.51

Solubility (Water)

8.81e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

oxazepam

IUPAC name

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

Synonyms

Oxazepam7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-1,4(2H)-benzodiazepin-2-oneOxazipamOxozepamOxazepamd-Oxazepam hemisuccinateAdumbranNSC 169448N-DesmethyltemazepamSerepaxDurazepamSerestaZaxopam7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-oneWy 3498Noctazepam7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-oneNesontilAnxiolit

Brand Name

Wy-3498 sticTazepamPsiquiwasNesontilTacepamQuilibrexVabenOxa-purenSobrilAdumbranAnsioxacepamPraxitenSerenidDrimuelNoctazepamAplakilSedigoaSerenalUskanLederpamRondarSerpaxDroxacepamEnidrelAzutranquilBonarePropaxAstressDurazepamPacienxSerestaHi-LongIsodinMurelaxSerepaxSigacalmQUENAnxiolitOxanidSeraxSerenid-DZaxopamNotaralLimbial

Names and Identifiers

Registration numbers

ATC CODE

MeSH Name

CHEMBL

EC Number

KEGG ID

Wikipedia Title

Chemspider ID

CAS Number

DrugBank ID

Unique Ingredient Identifier

6GOW6DWN2A

CHEBI ID

7823

PubChem CID

4616

PubChem SID

2489801416096418346506031

MDL Number

MFCD00057903

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Oxazepam

Sigma Aldrich

O5254

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

TRC

O845700

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. Pubmed

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. 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)

• Greenblatt, D.J., et al.: Clin. Pharmacokinet., 6, 89 (1971)

• Shearer, C.M., et al.: Anal. Profiles Drug Subs., 3, 441 (1971)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• IUPAC Traditional name

• IUPAC name

• Synonyms

• Brand Name

Registration numbers

• ATC CODE

• MeSH Name

• CHEMBL

• EC Number

• KEGG ID

• Wikipedia Title

• Chemspider ID

• CAS Number

• DrugBank ID

• Unique Ingredient Identifier

• CHEBI ID

• PubChem CID

• PubChem SID

• MDL Number

Registration numbers

Properties

• Physical Property

• Pharmacology Properties

• Safety Information

• Product Information

Related Proteins

Molecular Spectra

Molecule Details

• DrugBank

• Wikipedia

• Sigma Aldrich

• TRC

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Commercial Catalog

IUPAC Traditional name

oxazepam

IUPAC name

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

Synonyms

Brand Name

Wikipedia Title

Oxazepam

Unique Ingredient Identifier

6GOW6DWN2A

MDL Number

MFCD00057903

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

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]

• 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.

TRC

O845700

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

From Data Sources

• 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

• Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. Pubmed

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. 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)

• Greenblatt, D.J., et al.: Clin. Pharmacokinet., 6, 89 (1971)

• Shearer, C.M., et al.: Anal. Profiles Drug Subs., 3, 441 (1971)

Physical Property

Melting Point

205 - 206°C

Pharmacology Properties

Safety Information

Product Information

Certificate of Analysis

Download link

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Molecule

ID:720