lorazepam   Click here for help

GtoPdb Ligand ID: 5884

Synonyms: Ativan® | Orfidal®
Approved drug
lorazepam is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Lorazepam is used for the short-term management of severe anxiety. where it is thought to have a high affinity for GABA receptors. In March of 2016 it has also been reported as a GPR68 surrogate allosteric ligand [1].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: lorazepam

lorazepam is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 61.69
Molecular weight 320.01
XLogP 3.9
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES Clc1ccc2c(c1)C(=NC(C(=O)N2)O)c1ccccc1Cl
Isomeric 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)
InChI Key DIWRORZWFLOCLC-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Benzodiazepine class drugs
Approved drug? Yes (FDA (1977))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one
International Nonproprietary Names Click here for help
INN number INN
2809 lorazepam
Synonyms Click here for help
Ativan® | Orfidal®
Database Links Click here for help
Specialist databases
GPCRdb Ligand lorazepam
Other databases
CAS Registry No. 846-49-1 (source: SciFinder)
ChEMBL Ligand CHEMBL580
DrugBank Ligand DB00186
DrugCentral Ligand 1606
GtoPdb PubChem SID 178102508
PubChem CID 3958
Search Google for chemical match using the InChIKey DIWRORZWFLOCLC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DIWRORZWFLOCLC
Search PubMed clinical trials lorazepam
Search PubMed titles lorazepam
Search PubMed titles/abstracts lorazepam
UniChem Compound Search for chemical match using the InChIKey DIWRORZWFLOCLC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DIWRORZWFLOCLC-UHFFFAOYSA-N
Wikipedia Lorazepam

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

Tocris
Lorazepam (links to external site)
Cat. No. 3087