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846-49-1 molecular structure
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7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one

ChemBase ID: 71
Molecular Formular: C15H10Cl2N2O2
Molecular Mass: 321.1581
Monoisotopic Mass: 320.01193293
SMILES and InChIs

SMILES:
Clc1cc2C(=NC(O)C(=O)Nc2cc1)c1c(Cl)cccc1
Canonical SMILES:
Clc1ccc2c(c1)C(=NC(C(=O)N2)O)c1ccccc1Cl
InChI:
InChI=1S/C15H10Cl2N2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20)
InChIKey:
DIWRORZWFLOCLC-UHFFFAOYSA-N

Cite this record

CBID:71 http://www.chembase.cn/molecule-71.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one
IUPAC Traditional name
@lorazepam
lorazepam
Brand Name
Almazine
Alzapam
Anxiedin
Aplacassee
Ativan
Bonatranquan
Delormetazepam
Emotival
Idalprem
Lorabenz
Lorax
Loraz
Lorazepam Intensol
Lorsilan
Pro Dorm
Psicopax
Punktyl
Quait
Securit
Sedatival
Sedazin
Somagerol
Tavor
Temesta
Wypax
Ativan and others
Synonyms
(+/-)-Lorazepam
L-Lorazepam Acetate
O-Chlorooxazepam
O-Chloroxazepam
Lorazepam
7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one
(±)-Lorazepam
CAS Number
846-49-1
EC Number
212-687-6
MDL Number
MFCD00063406
PubChem SID
160963534
46508468
24896291
PubChem CID
3958
ATC CODE
N05BA06
CHEMBL
580
Chemspider ID
3821
DrugBank ID
DB00186
KEGG ID
D00365
Unique Ingredient Identifier
O26FZP769L
Wikipedia Title
Lorazepam
Medline Plus
a682053

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
L1764 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.606301  H Acceptors
H Donor LogD (pH = 5.5) 3.527322 
LogD (pH = 7.4) 3.527058  Log P 3.5273254 
Molar Refractivity 82.6992 cm3 Polarizability 31.031853 Å3
Polar Surface Area 61.69 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.98  LOG S -4.26 
Solubility (Water) 1.76e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Bioassay(PubChem)
Solubility
0.08 mg/mL expand Show data source
Hydrophobicity(logP)
3.5 expand Show data source
RTECS
DF0350000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
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 expand Show data source
Drug Control
USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Admin Routes
Oral, intramuscular, intravenous, sublingual, and transdermal expand Show data source
Bioavailability
85% of oral dose expand Show data source
Excretion
Renal expand Show data source
Half Life
9–16 hours expand Show data source
Metabolism
Hepatic glucuronidation expand Show data source
Legal Status
CD (Benz) POM (UK) expand Show data source
Schedule IV (Canada) expand Show data source
Schedule IV (US) expand Show data source
Pregnancy Category
D (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB00186 external link
Item Information
Drug Groups approved
Description A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent. [PubChem]
Indication For the management of anxiety disorders, and for treatment of status epilepticus.
Pharmacology Lorazepam, a benzodiazepine not transformed to active metabolites, is used to treat anxiety, status epilepticus, and for sedation induction and anterograde amnesia.
Toxicity Somnolence, confusion, and coma, LD50=3178mg/kg (orally in mice).
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Readily absorbed with an absolute bioavailability of 90%.
Half Life 12 hours
Protein Binding 85%
Elimination Lorazepam is rapidly conjugated at its 3-hydroxy group into lorazepam glucuronide which is then excreted in the urine.
References
Kemper N, Poser W, Poser S: [Benzodiazepine dependence: addiction potential of the benzodiazepines is greater than previously assumed (author's transl)] Dtsch Med Wochenschr. 1980 Dec 5;105(49):1707-12. [Pubmed]
Lader M: Short-term versus long-term benzodiazepine therapy. Curr Med Res Opin. 1984;8 Suppl 4:120-6. [Pubmed]
Maltais F, Laberge F, Laviolette M: A randomized, double-blind, placebo-controlled study of lorazepam as premedication for bronchoscopy. Chest. 1996 May;109(5):1195-8. [Pubmed]
Heisterkamp DV, Cohen PJ: The effect of intravenous premedication with lorazepam (ativan), pentobarbitone or diazepam on recall. Br J Anaesth. 1975 Jan;47(1):79-81. [Pubmed]
Milligan DW, Howard MR, Judd A: Premedication with lorazepam before bone marrow biopsy. J Clin Pathol. 1987 Jun;40(6):696-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - L1764 external link
Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L1764.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Kemper N, Poser W, Poser S: [Benzodiazepine dependence: addiction potential of the benzodiazepines is greater than previously assumed (author's transl)] Dtsch Med Wochenschr. 1980 Dec 5;105(49):1707-12. Pubmed
  • • Lader M: Short-term versus long-term benzodiazepine therapy. Curr Med Res Opin. 1984;8 Suppl 4:120-6. Pubmed
  • • Maltais F, Laberge F, Laviolette M: A randomized, double-blind, placebo-controlled study of lorazepam as premedication for bronchoscopy. Chest. 1996 May;109(5):1195-8. Pubmed
  • • Heisterkamp DV, Cohen PJ: The effect of intravenous premedication with lorazepam (ativan), pentobarbitone or diazepam on recall. Br J Anaesth. 1975 Jan;47(1):79-81. Pubmed
  • • Milligan DW, Howard MR, Judd A: Premedication with lorazepam before bone marrow biopsy. J Clin Pathol. 1987 Jun;40(6):696-8. Pubmed
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