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

• ChemBase ID: 116
• Molecular Formular: C16H13ClN2O2
• Molecular Mass: 300.73962
• Monoisotopic Mass: 300.06655535
• SMILES: Clc1cc2c(N(C(=O)C(O)N=C2c2ccccc2)C)cc1
• Canonical SMILES: Clc1ccc2c(c1)C(=NC(C(=O)N2C)O)c1ccccc1
• InChI: InChI=1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3
• InChIKey: SEQDDYPDSLOBDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-3-hydroxy-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: temazepam
• Brand Name: Apo-Temazepam; Cerepax; Crisonar; Euhypnos; Euipnos; Gelthix; Levanxene; Levanxol; Levanzene; Mabertin; Normison; Novo-Temazepam; Perdorm; Planum; Remestan; Restoril; Signopam; Temaz
• Synonyms: Temazepam; 7-Chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one; 3-Hydroxydiazepam; Normison; Perdorm; Planum; Remestan; Restoril; (+/-)-Temazepam; ER 115; NSC 246303; Ro 5-5354; Methyloxazepam; N-Methyloxazepam; Hydroxydiazepam; Oxydiazepam; Temazepam; 羟基安定

Database IDs

• CAS Number: 846-50-4
• EC Number: 212-688-1
• MDL Number: MFCD00057904
• PubChem SID: 24900518; 160963579; 46506604
• PubChem CID: 5391
• ATC CODE: N05CD07
• CHEMBL: 967
• Chemspider ID: 5198
• DrugBank ID: DB00231
• KEGG ID: D00370
• Unique Ingredient Identifier: CHB1QD2QSS
• Wikipedia Title: Temazepam
• Medline Plus: a684003

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.676493
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.787344
• LogD (pH = 7.4): 2.7871175
• Log P: 2.7873468
• Molar Refractivity: 81.0103 cm^3
• Polarizability: 30.94966 Å^3
• Polar Surface Area: 52.9 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.16
• LOG S: -3.75
• Solubility (Water): 5.34e-02 g/l

PROPERTIES

Physical Property

• Solubility: 164 mg/L; Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 74-79°C
• Hydrophobicity(logP): 3

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: DF1225000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 96%
• Excretion: Renal
• Half Life: 8–20 hours
• Metabolism: Hepatic
• Legal Status: ; IV (International); CD No Reg POM (UK); S4 (Australia); Schedule IV (Canada); Schedule IV (US)
• Pregnancy Category: C (Australia); X (US)

Product Information

• Grade: analytical standard
• Empirical Formula (Hill Notation): C16H13ClN2O2

DETAILS

DrugBank - DB00231

• Drug Groups: approved
• Description: A benzodiazepine that acts as a gamma-aminobutyric acid modulator and anti-anxiety agent. [PubChem]
• Indication: For the short-term treatment of insomnia (generally 7-10 days).
• Pharmacology: Temazepam is a benzodiazepine used as a hypnotic agent in the management of insomnia. Temazepam produces CNS depression at limbic, thalamic, and hypothalamic levels of the CNS. Temazepam increases the affinity of the neurotransmitter gamma-aminobutyric acid (GABA) for GABA receptors by binding to benzodiazepine receptors. Results are sedation, hypnosis, skeletal muscle relaxation, anticonvulsant activity, and anxiolytic action.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Temazepam is completely metabolized through conjugation prior to excretion. The major metabolite is the O-conjugate of temazepam (90%).
• Absorption: Well absorbed, minimal first-pass metabolism.
• Half Life: 10-20 hours
• Protein Binding: 96%
• Elimination: Temazepam was completely metabolized through conjugation prior to excretion; 80% to 90% of the dose appeared in the urine.
• References: Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [Pubmed] ; Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; Vozeh S: [Pharmacokinetic of benzodiazepines in old age] Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. [Pubmed] ; Shats V, Kozacov S: [Falls in the geriatric department: responsibility of the care-giver and the hospital] Harefuah. 1995 Jun 1;128(11):690-3, 743. [Pubmed] ; Rooke KC: The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice. J Int Med Res. 1976;4(5):355-9. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - T8275

Frequently Asked Questions
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Biochem/physiol Actions
Hypnotic

Toronto Research Chemicals - T017200

Pharmacologically active metabolite of Diazepam.Controlled substance (depressant). Sedative, hypnotic.

REFERENCES

• Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. Pubmed
• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• Vozeh S: [Pharmacokinetic of benzodiazepines in old age] Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. Pubmed
• Shats V, Kozacov S: [Falls in the geriatric department: responsibility of the care-giver and the hospital] Harefuah. 1995 Jun 1;128(11):690-3, 743. Pubmed
• Rooke KC: The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice. J Int Med Res. 1976;4(5):355-9. Pubmed
• Sarteschi, P., et al.: Arzneim.-Forsch., 22, 93 (1972)
• Schwandt, H.J., et al.: Xenobiotica, 4, 733 (1972)
• Curry, S.H., et al.: Br. J. Pharmacol., 57, 427 (1972)
• Heel, R.C., et al.: Drugs, 21, 321 (1972)