SynCED: Lorazepam

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:14 UTC

Update Date

2026-05-14 16:24:32 UTC

Accession Number

CHEM002139

Identification

Common Name

Lorazepam

Class

Small Molecule

Description

Lorazepam is only found in individuals that have used or taken this drug. It is 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]Lorazepam binds to an allosteric site on GABA-A receptors, which are pentameric ionotropic receptors in the CNS. Binding potentiates the effects of the inhibitory neurotransmitter GABA, which upon binding opens the chloride channel in the receptor, allowing chloride influx and causing hyperpolerization of the neuron.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Anxiety Agent
Anticonvulsant
Antiemetic
Benzodiazepine
Drug
GABA Modulator
Human Neurotoxin
Hypnotic and Sedative
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ativan	Kegg
(+/-)-lorazepam	HMDB
O-Chlorooxazepam	HMDB
O-Chloroxazepam	HMDB
AHP brand OF lorazepam	MeSH, HMDB
apo Lorazepam	MeSH, HMDB
Llorens brand OF lorazepam	MeSH, HMDB
Lorazepam ahp brand	MeSH, HMDB
Lorazepam baxter brand	MeSH, HMDB
Lorazepam medical	MeSH, HMDB
Lorazepam medix brand	MeSH, HMDB
Lorazepam wyeth brand	MeSH, HMDB
Lorazepam neuraxpharm brand	MeSH, HMDB
Lorazepam ratiopharm brand	MeSH, HMDB
Medix brand OF lorazepam	MeSH, HMDB
novo Lorazem	MeSH, HMDB
novo-Lorazem	MeSH, HMDB
Novopharm brand OF lorazepam	MeSH, HMDB
Lorazep von CT	MeSH, HMDB
Neuraxpharm brand OF lorazepam	MeSH, HMDB
Ratiopharm brand OF lorazepam	MeSH, HMDB
Dolorgiet brand OF lorazepam	MeSH, HMDB
Duralozam	MeSH, HMDB
Laubeel	MeSH, HMDB
Lorazepam apotex brand	MeSH, HMDB
Lorazepam desitin brand	MeSH, HMDB
Lorazepam CT-arzneimittel brand	MeSH, HMDB
Lorazepam-ratiopharm	MeSH, HMDB
Merck dura brand OF lorazepam	MeSH, HMDB
Nu-loraz	MeSH, HMDB
Riemser brand OF lorazepam	MeSH, HMDB
Serra pamies brand OF lorazepam	MeSH, HMDB
Sinestron	MeSH, HMDB
Temesta	MeSH, HMDB
Tolid	MeSH, HMDB
Wyeth, orfidal	MeSH, HMDB
CT Arzneimittel brand OF lorazepam	MeSH, HMDB
ApoLorazepam	MeSH, HMDB
Baxter brand OF lorazepam	MeSH, HMDB
Idalprem	MeSH, HMDB
Lorazepam dolorgiet brand	MeSH, HMDB
Lorazepam medical brand	MeSH, HMDB
Lorazepam novartis brand	MeSH, HMDB
Lorazepam riemser brand	MeSH, HMDB
Lorazepam ratiopharm	MeSH, HMDB
Lorazepam-neuraxpharm	MeSH, HMDB
Medical brand OF lorazepam	MeSH, HMDB
Medical, lorazepam	MeSH, HMDB
NovoLorazem	MeSH, HMDB
Nu loraz	MeSH, HMDB
Orfidal wyeth	MeSH, HMDB
Somagerol	MeSH, HMDB
apo-Lorazepam	MeSH, HMDB
Apotex brand OF lorazepam	MeSH, HMDB
Desitin brand OF lorazepam	MeSH, HMDB
Donix	MeSH, HMDB
Durazolam	MeSH, HMDB
Lorazepam llorens brand	MeSH, HMDB
Lorazepam novopharm brand	MeSH, HMDB
Lorazepam nu-pharm brand	MeSH, HMDB
Lorazepam neuraxpharm	MeSH, HMDB
Novartis brand OF lorazepam	MeSH, HMDB
Nu pharm brand OF lorazepam	MeSH, HMDB
Nu-pharm brand OF lorazepam	MeSH, HMDB
NuLoraz	MeSH, HMDB
Sedicepan	MeSH, HMDB
Wyeth brand OF lorazepam	MeSH, HMDB
CT-Arzneimittel brand OF lorazepam	MeSH, HMDB
Von CT, lorazep	MeSH, HMDB

Chemical Formula

C₁₅H₁₀Cl₂N₂O₂

Average Molecular Mass

321.158 g/mol

Monoisotopic Mass

320.012 g/mol

CAS Registry Number

846-49-1

IUPAC Name

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

Traditional Name

lorazepam

SMILES

OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=C2

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Secondary carboxylic acid amide
Lactam
Alkanolamine
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Imine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	192-194°C
Boiling Point	Not Available
Solubility	80 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.53	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	10.61	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.7 m³·mol⁻¹	ChemAxon
Polarizability	30.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Parenteral (intravenous, sublingual); oral. Readily absorbed with an absolute bioavailability of 90% when given orally. When intramuscularly administered, lorazepam is completely and rapidly absorbed. It achieves max serum concentration in 3 hours. The max serum concentration of a 4 mg dose is 48 ng/mL.

Mechanism of Toxicity

Lorazepam binds to an allosteric site on GABA-A receptors, which are pentameric ionotropic receptors in the CNS. Binding potentiates the effects of the inhibitory neurotransmitter GABA, which upon binding opens the chloride channel in the receptor, allowing chloride influx and causing hyperpolerization of the neuron.

Metabolism

Lorazepam is hepatically metabolized and is extensively conjugated to the 3-0-phenolic glucuronide. This is an inactive metabolite and is eliminated mainly by the kidneys. Route of Elimination: When a single 2 mg oral dose is give to healthy subjects, 88±4% of the administered dose was recovered in urine and 7±2% was recovered in feces. The percent of administered dose recovered in urine as lorazepam glucuronide was 74±4%. Only 0.3% of the dose was recovered as unchanged lorazepam, and the remainder of the radioactivity represented minor metabolites. Half Life: Parenteral administration = 14±5 hours; Oral administration = 2 hours.

Toxicity Values

LD50, mouse, oral = 1850 mg/kg LD50: 3178mg/kg (oral, mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the management of anxiety disorders, and for treatment of status epilepticus.

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Somnolence, confusion, and coma.

Treatment

General supportive and symptomatic measures are recommended. Vital signs must be monitored and the patient closely observed. When there is a risk of aspiration, induction of emesis is not recommended. Gastric lavage may be indicated if performed soon after ingestion or in symptomatic patients. Administration of activated charcoal may also limit drug absorption. (7)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

3821

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Igor Lifshitz, “Process for preparing pure crystalline lorazepam.” U.S. Patent US20010039340, issued November 08, 2001.

MSDS

Link

General References

Lorazepam (CHEM002139)

Structure for CHEM002139: Lorazepam