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846-50-4 molecular structure
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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 and InChIs

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

Cite this record

CBID:116 http://www.chembase.cn/molecule-116.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Methyloxazepam
N-Methyloxazepam
Hydroxydiazepam
Oxydiazepam
Temazepam
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
羟基安定
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.676493  H Acceptors
H Donor LogD (pH = 5.5) 2.787344 
LogD (pH = 7.4) 2.7871175  Log P 2.7873468 
Molar Refractivity 81.0103 cm3 Polarizability 30.94966 Å3
Polar Surface Area 52.9 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.16  LOG S -3.75 
Solubility (Water) 5.34e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
164 mg/L expand Show data source
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
74-79°C expand Show data source
Hydrophobicity(logP)
3 expand Show data source
Storage Condition
Controlled Substance, -20°C Freezer expand Show data source
RTECS
DF1225000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Drug Control
USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
96% expand Show data source
Excretion
Renal expand Show data source
Half Life
8–20 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status

IV (International)
expand Show data source
CD No Reg POM (UK) expand Show data source
S4 (Australia) expand Show data source
Schedule IV (Canada) expand Show data source
Schedule IV (US) expand Show data source
Pregnancy Category
C (Australia) expand Show data source
X (US) expand Show data source
Grade
analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C16H13ClN2O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia TRC TRC
DrugBank - DB00231 external link
Item Information
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 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Hypnotic
Toronto Research Chemicals - T017200 external link
Pharmacologically active metabolite of Diazepam.Controlled substance (depressant). Sedative, hypnotic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
  • • 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
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PATENTS

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