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Compound Detail

CHEMBL580

LORAZEPAM
💊 Approved Drug
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💊 Approved Drug
O=C1Nc2ccc(Cl)cc2C(c2ccccc2Cl)=NC1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL580
Name LORAZEPAM
Phase Approved
Structure Type MOL
InChI Key DIWRORZWFLOCLC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Abbloraz Ativan Loraz Lorazepam Lorazepam civ Lorazepam intensol Lorazepam preservative free Loreev xr NSC-289758 Temesta WY-4036
2
Targets
9
Activities
2
Assay Types
27
PK Parameters
20
Publications
11
Known Names
20
Indications
1
Mechanisms

Molecular Properties

321.2
MW (Da)
3.10
ALogP
3
HBA
2
HBD
61.7
PSA (Ų)
0.85
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -azepam
USAN Year 1969

Extended Properties

Molecular Formula C15H10Cl2N2O2
MW 321.16
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.37

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR GABA-A receptor; anion channel ✓ ✓

Indications

Anxiety Anxiety Disorders Depression Status Epilepticus Dementia Depressive Disorder Epilepsia Partialis Continua Epilepsy Psychomotor Agitation Psychotic Disorders Schizophrenia Vertigo Alcoholism Amphetamine-Related Disorders Cocaine-Related Disorders Delirium Down Syndrome Epilepsy, Reflex Pain Seizures

ATC Classification

N05BA06
lorazepam
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS
N05BA56
lorazepam, combinations
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning
General Warning
Country: United States
Black Box Warning
misuse
Country: United States

Activity Summary

Ki 6 meas. best 8.29
IC50 3 meas. best 8.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 8.29 8.29 5.2 1
Unchecked
CHEMBL612545
 IC50 8.2 8.2 6.4 1
Fatty acid-binding protein, liver
CHEMBL5738
 Ki 4.89 4.89 12900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 27.2 mL.min-1.kg-1 Rattus norvegicus
CL 26.1 mL.min-1.kg-1 Canis lupus familiaris
CL 1.1 mL.min-1.kg-1 Homo sapiens
CL 1.1 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 4.57 uL.min-1.(10^6cells)-1 Homo sapiens
CL 7.94 mL.min-1.g-1 Homo sapiens
CL 17.38 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 1.21 mL.min-1.kg-1 Homo sapiens
CL 1.21 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.09 - -
Fu 0.029 - -
Fu 0.09 - Homo sapiens
Fu 0.09 - Homo sapiens
Fu 0.09 - Homo sapiens
Fu 0.158 - Mus musculus
Fu 0.103 - Macaca mulatta
Fu 0.09 - Rattus norvegicus
Fu 0.073 - Canis lupus familiaris
Fu 0.057 - Homo sapiens
MRT 22.0 hr Homo sapiens
T1/2 17.0 hr Homo sapiens
T1/2 12.4 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 5.177 nM 8.29 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -
Unchecked IC50 = 6.354 nM 8.2 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -
Fatty acid-binding protein, liver Ki = 12900.0 nM 4.89 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 613
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
12061889 10.1021/jm0200409 ADMET 5
21282406 10.1124/dmd.110.037457 Plasma 5
21282406 10.1124/dmd.110.037457 Nucleic Acid 5
21282406 10.1124/dmd.110.037457 ADMET 5
- 10.6019/CHEMBL3301361 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
26550826 10.1038/nature15699 Ovarian cancer G-protein coupled receptor 1 4
21282406 10.1124/dmd.110.037457 Homo sapiens 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
7359533 10.1021/jm00176a016 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
15781124 10.1016/j.pharmthera.2004.10.013 Unchecked 3

Data from ChEMBL 36 via Core Engine