Identification

Name
Oxazepam
Accession Number
DB00842  (APRD01152)
Type
Small Molecule
Groups
Approved
Description

Oxazepam is an intermediate-acting, 3-hydroxybenzodiazepine used in the treatment of alcohol withdrawal and anxiety disorders. Oxazepam, like related 3-hydroxybenzodiazepine lorazepam, is considered less susceptible to pharmacokinetic variability based on patient-specific factors (e.g. age, liver disease) - this feature is advantageous as compared to other benzodiazepines, and is likely owing in part to oxazepam's relatively simple metabolism.11 It is an active metabolite of both diazepam and temazepam12 and undergoes very little biotransformation following absorption, making it unlikely to participate in pharmacokinetic interactions.13

Structure
Thumb
Synonyms
  • (+-)-Oxazepam
  • (RS)-Oxazepam
  • Oxazepam
External IDs
J3.308A / NSC-169448 / WY-3498
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novoxapam Tab 10mgTabletOralNovopharm Limited1982-12-312015-10-26Canada
Novoxapam Tab 15mgTabletOralNovopharm Limited1982-12-312015-10-26Canada
Novoxapam Tab 30mgTabletOralNovopharm Limited1982-12-312015-10-26Canada
Oxazepam 10 Tab 10mgTabletOralPro Doc Limitee1980-12-31Not applicableCanada
Oxazepam 10mg TabletsTabletOralLaboratoires Confab IncNot applicableNot applicableCanada
Oxazepam 15 Tab 15mgTabletOralPro Doc Limitee1980-12-31Not applicableCanada
Oxazepam 15mg TabletsTabletOralLaboratoires Confab IncNot applicableNot applicableCanada
Oxazepam 30 Tab 30mgTabletOralPro Doc Limitee1980-12-31Not applicableCanada
Oxazepam 30mg TabletsTabletOralLaboratoires Confab IncNot applicableNot applicableCanada
Oxazepam Tablets 15mgTabletOralD.C. Labs Limited1980-12-312003-07-11Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Oxazepam Tab 10mgTabletOralApotex Corporation1979-12-31Not applicableCanada
Apo Oxazepam Tab 15mgTabletOralApotex Corporation1979-12-31Not applicableCanada
Apo Oxazepam Tab 30mgTabletOralApotex Corporation1979-12-31Not applicableCanada
Bio-oxazepamTabletOralBiomed Pharma2003-04-23Not applicableCanada
Bio-oxazepamTabletOralBiomed Pharma2003-04-23Not applicableCanada
Bio-oxazepamTabletOralBiomed Pharma2003-04-23Not applicableCanada
OxazepamCapsule15 mg/1OralTrupharma, Llc2020-05-15Not applicableUs
OxazepamCapsule15 mg/1Oralbryant ranch prepack2011-01-062013-06-01Us
OxazepamCapsule15 mg/1OralAphena Pharma Solutions Tennessee, Inc.1988-04-192019-08-31Us
OxazepamCapsule10 mg/1OralTrupharma, Llc2020-05-15Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Adumbran / Alepam / Alopam / Anxiolit / Durazepam / Limbial / Medopam / Murelax / Noripam / Opamox / Ox-Pam / Oxascand / Praxiten / Purata / Serax (Landsteiner (Mexico)) / Serenal / Serenid / Serepax / Seresta / Serpax / Sobril / Tazepam / Vaben / Zaxpam
Categories
UNII
6GOW6DWN2A
CAS number
604-75-1
Weight
Average: 286.713
Monoisotopic: 286.050905313
Chemical Formula
C15H11ClN2O2
InChI Key
ADIMAYPTOBDMTL-UHFFFAOYSA-N
InChI
InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)
IUPAC Name
7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
SMILES
OC1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2

Pharmacology

Indication

Oxazepam is indicated for the management of anxiety disorders and for the short-term relief of symptoms of anxiety.13 It may also be used in the management of alcohol withdrawal symptoms.13

Associated Conditions
Pharmacodynamics

Benzodiazepines, including oxazepam, exert their sedative and anxiolytic effects by potentiating the effects of endogenous GABA, the primary inhibitory neurotransmitter in the CNS.10 Compared to other benzodiazepines, it has relatively low potency and a moderate duration of action.10 Oxazepam should be administered with caution to patients for whom a drop in blood pressure may lead to cardiac complications as, in rare cases, it may cause hypotension.13

Mechanism of action

Like other benzodiazepines, oxazepam exerts its anxiolytic effects by potentiating the effect of gamma-aminobutyric acid (GABA) on GABA(A) receptors, the main inhibitory neurotransmitter receptors in the mammalian brain.8 GABA(A) receptors are a component of GABA-gated ionotropic chloride channels that produce inhibitory postsynaptic potentials - following activation by GABA, the channel undergoes a conformational change that allows the passage of chloride ions through the channel. The inhibitory potentials produced by GABA neurotransmission play an integral role in the suppression and control of epileptiform nerve firing such as that seen in epilepsy, which makes the GABA system a desirable target in the treatment of epilepsy.

Benzodiazepines are positive allosteric modulators of GABA(A) function. They bind to the interface between alpha (α) and gamma (γ) subunits on the receptor, commonly referred to as the benzodiazepine binding site, and modulate the receptor such that its inhibitory response to GABA binding is dramatically increased.8

TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Following oral administration, peak plasma levels (Cmax) averaged 450 mg/mL and occurred approximately 3 hours (Tmax) after dosing.13

Volume of distribution
Not Available
Protein binding

Plasma protein binding is approximately 89%,14 likely to albumin.7

Metabolism

Oxazepam has a single major inactive metabolite, a glucuronide conjugate.13 The glucuronidation of the S-isomer is catalyzed by UGT2B15. The glucuronidation of the R-isomer is catalyzed by UGT2B7 and UGT1A9.[A18016]

Route of elimination

Oxazepam is primarily eliminated in the urine as its glucuronide metabolite, with the feces containing approximately 21% of the unchanged drug.14 The majority of an orally ingested dose of oxazepam is excreted within 48 hours.14

Half life

The mean elimination half-life of oxazepam is 8.2 hours.13

Clearance
Not Available
Toxicity

The oral LD50 in rats and mice is >8000 mg/kg and 1540 mg/kg, respectively.15

Symptoms of oxazepam overdose are likely to be consistent with its adverse effect profile and range from mild to severe, sometimes fatal, CNS depression.13 Treatment should include gastric decontamination, via lavage or induced vomiting, followed by symptomatic and supportive measures. The benzodiazepine antagonist flumazenil may be used in hospitalized patients as an adjunct to non-pharmacological management, but may increase the risk of seizure in long-term benzodiazepine users and in cyclic antidepressant overdose.13

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Oxazepam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe therapeutic efficacy of Oxazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Oxazepam is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Oxazepam is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Oxazepam is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe therapeutic efficacy of Oxazepam can be decreased when used in combination with 6-O-benzylguanine.
7-DeazaguanineThe therapeutic efficacy of Oxazepam can be decreased when used in combination with 7-Deazaguanine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Oxazepam is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Oxazepam is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
7,9-DimethylguanineThe therapeutic efficacy of Oxazepam can be decreased when used in combination with 7,9-Dimethylguanine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol. Co-administration with alcohol may potentiate the CNS effects of oxazepam.

References

General References
  1. Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. [PubMed:8700792]
  2. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616]
  3. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed:2570451]
  4. Christensen P, Lolk A, Gram LF, Kragh-Sorensen P: Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers. Psychopharmacology (Berl). 1992;106(4):511-6. [PubMed:1349754]
  5. Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine]. Arch Fr Pediatr. 1977 Jan;34(1):74-89. [PubMed:851373]
  6. Altamura AC, Moliterno D, Paletta S, Maffini M, Mauri MC, Bareggi S: Understanding the pharmacokinetics of anxiolytic drugs. Expert Opin Drug Metab Toxicol. 2013 Apr;9(4):423-40. doi: 10.1517/17425255.2013.759209. Epub 2013 Jan 21. [PubMed:23330992]
  7. Chin PK, Jensen BP, Larsen HS, Begg EJ: Adult age and ex vivo protein binding of lorazepam, oxazepam and temazepam in healthy subjects. Br J Clin Pharmacol. 2011 Dec;72(6):985-9. doi: 10.1111/j.1365-2125.2011.04036.x. [PubMed:21671987]
  8. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [PubMed:23038269]
  9. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [PubMed:29950725]
  10. Griffin CE 3rd, Kaye AM, Bueno FR, Kaye AD: Benzodiazepine pharmacology and central nervous system-mediated effects. Ochsner J. 2013 Summer;13(2):214-23. [PubMed:23789008]
  11. Shader RI, Greenblatt DJ: The use of benzodiazepines in clinical practice. Br J Clin Pharmacol. 1981;11 Suppl 1:5S-9S. doi: 10.1111/j.1365-2125.1981.tb01832.x. [PubMed:6133535]
  12. Calcaterra NE, Barrow JC: Classics in chemical neuroscience: diazepam (valium). ACS Chem Neurosci. 2014 Apr 16;5(4):253-60. doi: 10.1021/cn5000056. Epub 2014 Feb 27. [PubMed:24552479]
  13. FDA Approved Drug Products: Oxazepam oral capsules [Link]
  14. Health Canada Product Monograph: Oxazepam oral tablets [Link]
  15. CaymanChem: Oxazepam MSDS [Link]
External Links
Human Metabolome Database
HMDB0061121
KEGG Drug
D00464
KEGG Compound
C07359
PubChem Compound
4616
PubChem Substance
46506031
ChemSpider
4455
BindingDB
85031
RxNav
7781
ChEBI
7823
ChEMBL
CHEMBL568
Therapeutic Targets Database
DAP000243
PharmGKB
PA450731
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Oxazepam
ATC Codes
N05BA04 — Oxazepam
AHFS Codes
  • 28:24.08 — Benzodiazepines
MSDS
Download (44.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCocaine Use Disorders1
1CompletedTreatmentCocaine Use Disorders / Tobacco Use Disorders1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia1
4CompletedTreatmentAlcohol Dependence / Alcohol Withdrawal Syndrome(AWS)1
Not AvailableCompletedTreatmentDependence, Cocaine1

Pharmacoeconomics

Manufacturers
  • Actavis elizabeth llc
  • American therapeutics inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Watson laboratories inc
  • Alpharma us pharmaceuticals division
  • Quantum pharmics ltd
  • Parke davis div warner lambert co
Packagers
  • Actavis Group
  • Amerisource Health Services Corp.
  • Centaur Pharmaceuticals Pvt Ltd.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Remedy Repack
  • Sandoz
  • Stat Rx Usa
Dosage forms
FormRouteStrength
TabletOral
CapsuleOral10 mg/1
CapsuleOral15 mg/1
CapsuleOral30 mg/1
Capsule, gelatin coatedOral10 mg/1
Capsule, gelatin coatedOral15 mg/1
Capsule, gelatin coatedOral30 mg/1
Prices
Unit descriptionCostUnit
Oxazepam 30 mg capsule1.2USD capsule
Serax 10 mg capsule1.17USD capsule
Oxazepam 15 mg capsule0.73USD capsule
Oxazepam 10 mg capsule0.6USD capsule
Apo-Oxazepam 30 mg Tablet0.09USD tablet
Apo-Oxazepam 15 mg Tablet0.07USD tablet
Apo-Oxazepam 10 mg Tablet0.04USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205-206 °CPhysProp
logP2.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0881 mg/mLALOGPS
logP2.01ALOGPS
logP2.92ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.61ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.89 m3·mol-1ChemAxon
Polarizability28.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9826
Blood Brain Barrier+0.9641
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.517
P-glycoprotein inhibitor INon-inhibitor0.8866
P-glycoprotein inhibitor IINon-inhibitor0.9167
Renal organic cation transporterNon-inhibitor0.8812
CYP450 2C9 substrateNon-substrate0.7692
CYP450 2D6 substrateNon-substrate0.8685
CYP450 3A4 substrateSubstrate0.5631
CYP450 1A2 substrateInhibitor0.8262
CYP450 2C9 inhibitorNon-inhibitor0.5063
CYP450 2D6 inhibitorNon-inhibitor0.8445
CYP450 2C19 inhibitorInhibitor0.5065
CYP450 3A4 inhibitorNon-inhibitor0.6563
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6407
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7711
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8229 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.999
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0699-7490000000-e90f4b8174c78110a07a
GC-MS Spectrum - EI-BGC-MSsplash10-0pxr-6490000000-98a9035e85eeea7c02e5
Mass Spectrum (Electron Ionization)MSsplash10-05r0-5590000000-87245820addec0215473
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-dc62fcc1bbffbe41a418
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0090000000-0babffe4ebd04774afee
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0090000000-93028caba51f80d16e67
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0490000000-e36258d846328fd12f7d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-d4bd0b0355dc42f3606f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0090000000-cb90c6162b5e9a189120
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0090000000-cfdd9662d1f355ecf572
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-052f-0090000000-1c26508a42811abbe1cb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udl-0980000000-870c5260836b760916d2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-f0561f08464034626ee2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-d55c5dfc5658fa7a4e05
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0090000000-7682f5c8dc13b49aa59e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-526eef46646595e92a99
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-21ba02c0de7b6e8c51ff
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014r-0090000000-61c68689382573975141
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-74e04f10a2b801bba9ba
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0490000000-31f82dff12f0e9088719
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f6x-0960000000-90758cc09aa77510b07c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0w2c-1920000000-c885875f53b407082d2c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-ff519596d2f3661430c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kr-0090000000-be9b911b5bceb5198ddf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-0f188e3108f6469a5b48
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0490000000-42926fc509d963549129
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f6x-0960000000-38ad8b94aca33eb321e0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udl-1920000000-5bbf6943424b7702e596
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-e8e44c252369ee147dfb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00ko-0190000000-28e03cc6951a989a43bb

Taxonomy

Description
This compound 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
Benzene and substituted derivatives / Aryl chlorides / Cyclic carboximidic acids / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Alkanolamines / Organopnictogen compounds / Organooxygen compounds / Organochlorides
show 1 more
Substituents
1,4-benzodiazepine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Cyclic carboximidic acid / Ketimine / Alkanolamine / Azacycle / Organic 1,3-dipolar compound
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, 1,4-benzodiazepinone (CHEBI:7823)

Targets

Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
Curator comments
The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [PubMed:23038269]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [PubMed:29950725]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
Curator comments
Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [PubMed:23038269]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [PubMed:29950725]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. Court MH, Duan SX, Guillemette C, Journault K, Krishnaswamy S, Von Moltke LL, Greenblatt DJ: Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos. 2002 Nov;30(11):1257-65. [PubMed:12386133]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Court MH, Duan SX, Guillemette C, Journault K, Krishnaswamy S, Von Moltke LL, Greenblatt DJ: Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos. 2002 Nov;30(11):1257-65. [PubMed:12386133]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Court MH, Duan SX, Guillemette C, Journault K, Krishnaswamy S, Von Moltke LL, Greenblatt DJ: Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos. 2002 Nov;30(11):1257-65. [PubMed:12386133]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Chin PK, Jensen BP, Larsen HS, Begg EJ: Adult age and ex vivo protein binding of lorazepam, oxazepam and temazepam in healthy subjects. Br J Clin Pharmacol. 2011 Dec;72(6):985-9. doi: 10.1111/j.1365-2125.2011.04036.x. [PubMed:21671987]

Drug created on June 13, 2005 07:24 / Updated on July 09, 2020 11:59

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