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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL580
CHEMBL580
Compound Name LORAZEPAM
ChEMBL Synonyms LORAZEPAM PRESERVATIVE FREE | ATIVAN | LORAZEPAM INTENSOL | TEMESTA | ABBLORAZ | LORAZ | LORAZEPAM | WY-4036
Max Phase 4 (Approved)
Trade Names ATIVAN | LORAZEPAM PRESERVATIVE FREE | LORAZEPAM | ABBLORAZ | LORAZ | TEMESTA | LORAZEPAM INTENSOL
Molecular Formula C15H10Cl2N2O2

Additional synonyms for CHEMBL580 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OC1N=C(c2ccccc2Cl)c3cc(Cl)ccc3NC1=O
Standard InChI InChI=1S/C15H10Cl2N2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20 ...
Download InChI
Standard InChI Key DIWRORZWFLOCLC-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL580

Molecule Features

CHEMBL580 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
GABA-A receptor; anion channel positive allosteric modulator GABA-A receptor; anion channel PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
NauseaD009325HP:0002018Nausea2ClinicalTrials
Substance-Related DisordersD019966EFO:0003890drug dependence1ClinicalTrials
VomitingD0148392ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
Anxiety DisordersD001008EFO:0006788anxiety disorder4DailyMed
DementiaD003704HP:0000726dementia3ClinicalTrials
SeizuresD012640HP:0001250Seizures2ClinicalTrials
Substance Withdrawal SyndromeD013375EFO:0004777alcohol withdrawal2ClinicalTrials
DepressionD003863EFO:0003761unipolar depression4DailyMed
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer2ClinicalTrials
Psychomotor AgitationD0115953ClinicalTrials
Psychotic DisordersD011618EFO:0005411schizoaffective disorder3ClinicalTrials
AnxietyD001007EFO:0005230anxiety4ATC
ATC
ClinicalTrials
Epilepsia Partialis ContinuaD017036EFO:1000924epilepsia partialis continua3ClinicalTrials
Obsessive-Compulsive DisorderD009771EFO:0004242obsessive-compulsive disorder2ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease1ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
EpilepsyD004827EFO:0000474epilepsy3ClinicalTrials
Epilepsy, ReflexD020195EFO:1001146reflex epilepsy2ClinicalTrials

Clinical Data

ClinicalTrials.gov LORAZEPAM
The Cochrane Collaboration LORAZEPAM

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL580. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.378
CHEMBL5023 p53-binding protein Mdm-2 Homo sapiens 0.315
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 0.268

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5023 p53-binding protein Mdm-2 Homo sapiens 0.747
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 0.397

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
321.2 320.0119 3.1 1 61.69 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
10.8 .17 2.38 2.38 2 21 0.85

Structural Alerts

There are no structural alerts for CHEMBL580

Compound Cross References

ATC N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05B - ANXIOLYTICS
N05BA - Benzodiazepine derivatives
N05BA06 - lorazepam

N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05B - ANXIOLYTICS
N05BA - Benzodiazepine derivatives
N05BA56 - lorazepam, combinations

ChemSpider ChemSpider:DIWRORZWFLOCLC-UHFFFAOYSA-N
DailyMed lorazepam
PubChem SID: 144205222 SID: 29215381
Wikipedia Lorazepam

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL580



ACToR 846-49-1
BindingDB 50292627
Brenda 8612
ChEBI 6539
DrugBank DB00186
DrugCentral 1606
eMolecules 552192
EPA CompTox Dashboard DTXSID7023225
Guide to Pharmacology 5884
Human Metabolome Database HMDB0014332
IBM Patent System 929F4A85E5858DAE3698E6310A03BAE1
LINCS LSM-4970
NIH Clinical Collection SAM001246833
Nikkaji J3.337E
PharmGKB PA450267
PubChem 3958
PubChem: Thomson Pharma 14801418
SureChEMBL SCHEMBL26961

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/DIWRORZWFLOCLC-UHFFFAOYSA-N spacer
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