CAS 846-49-1|L-Lorazepam Acetate|O-Chloroxazepam|lorazepam|Lorazepam|Ativan and others|7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one|7-Chloro-5-(2-chlorophenyl)-1,3-di...

General Information

Structure

Molecular Formula

C₁₅H₁₀Cl₂N₂O₂

Molecular Mass

321.1581

Exact Mass

320.01193293

Charge

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

Canonic Smiles

Clc1ccc2c(c1)C(=NC(C(=O)N2)O)c1ccccc1Cl

Isomeric Smiles

Clc1cc2C(=NC(O)C(=O)Nc2cc1)c1c(Cl)cccc1

Calculated Properties

JChem

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

Polarizability

31.031853

Polar Surface Area

61.69

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.98

LOG S

-4.26

Solubility (Water)

1.76e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

lorazepam @lorazepam

IUPAC name

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

Synonyms

L-Lorazepam AcetateO-ChloroxazepamLorazepam7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one(±)-LorazepamO-Chlorooxazepam(+/-)-Lorazepam

Brand Name

Ativan and othersQuaitAnxiedinPsicopaxLorazAlmazineSedativalWypaxAlzapamTemestaEmotivalIdalpremLoraxAtivanBonatranquanSecuritLorsilanAplacasseeSomagerolDelormetazepamTavorSedazinPro DormLorazepam IntensolLorabenzPunktyl

Names and Identifiers

Registration numbers

CHEMBL

PubChem CID

ATC CODE

Chemspider ID

CAS Number

KEGG ID

Medline Plus

DrugBank ID

Wikipedia Title

Unique Ingredient Identifier

O26FZP769L

EC Number

212-687-6

PubChem SID

4650846824896291160963534

MDL Number

MFCD00063406

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.5

Solubility

0.08 mg/mL

Pharmacology Properties

Legal Status

Schedule IV (Canada)

CD (Benz) POM (UK)

Schedule IV (US)

Pregnancy Category

D (US)

Bioavailability

85% of oral dose

Metabolism

Hepatic glucuronidation

Admin Routes

Oral, intramuscular, intravenous, sublingual, and transdermal

Half Life

9–16 hours

Excretion

Renal

Safety Information

Drug Control

USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

GHS Hazard statements

H361

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

36/37

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Warning

P281

Harmful (Xn)

DF0350000

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00186

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]

Wikipedia

Lorazepam

Sigma Aldrich

L1764

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.

Molecule Details

References

PubChem Literature

From Data Sources

• Milligan DW, Howard MR, Judd A: Premedication with lorazepam before bone marrow biopsy. J Clin Pathol. 1987 Jun;40(6):696-8. 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

• 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

• Lader M: Short-term versus long-term benzodiazepine therapy. Curr Med Res Opin. 1984;8 Suppl 4:120-6. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC Traditional name

lorazepam @lorazepam

IUPAC name

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

Synonyms

L-Lorazepam AcetateO-ChloroxazepamLorazepam7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one(±)-LorazepamO-Chlorooxazepam(+/-)-Lorazepam

Brand Name

Registration numbers

CHEMBL

PubChem CID

ATC CODE

Chemspider ID

CAS Number

KEGG ID

Medline Plus

DrugBank ID

Wikipedia Title

Unique Ingredient Identifier

O26FZP769L

EC Number

212-687-6

PubChem SID

4650846824896291160963534

MDL Number

MFCD00063406

Molecule Details

DrugBank

DB00186

Drug Groups

approved

Description

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

• 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]

Wikipedia

Lorazepam

Sigma Aldrich

L1764

References

PubChem Literature

From Data Sources

• Milligan DW, Howard MR, Judd A: Premedication with lorazepam before bone marrow biopsy. J Clin Pathol. 1987 Jun;40(6):696-8. 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

• 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

• Lader M: Short-term versus long-term benzodiazepine therapy. Curr Med Res Opin. 1984;8 Suppl 4:120-6. Pubmed

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

3.5

Solubility

0.08 mg/mL

Pharmacology Properties

Legal Status

Schedule IV (Canada)

CD (Benz) POM (UK)

Schedule IV (US)

Pregnancy Category

D (US)

Bioavailability

85% of oral dose

Metabolism

Hepatic glucuronidation

Admin Routes

Oral, intramuscular, intravenous, sublingual, and transdermal

Half Life

9–16 hours

Excretion

Renal

Safety Information

Drug Control

USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

GHS Hazard statements

H361

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

36/37

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Warning

P281

Harmful (Xn)

DF0350000

Molecule

ID:71