Identification

Name
Naltrexone
Accession Number
DB00704
Description

Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of naloxone. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 341.4009
Monoisotopic: 341.162708229
Chemical Formula
C20H23NO4
Synonyms
  • 17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one
  • 17-(Cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one
  • N-Cyclopropylmethyl-14-hydroxydihydromorphinone
  • N-Cyclopropylmethylnoroxymorphone
  • Naltrexon
  • Naltrexona
  • Naltrexone
  • Naltrexonum
External IDs
  • EN-1639 A
  • PTI-901
  • UM 792

Pharmacology

Indication

Used as an adjunct to a medically supervised behaviour modification program in the maintenance of opiate cessation in individuals who were formerly physically dependent on opiates and who have successfully undergone detoxification. Also used for the management of alcohol dependence in conjunction with a behavioural modification program.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Naltrexone, a pure opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone is indicated in the treatment of alcohol dependence and for the blockade of the effects of exogenously administered opioids. It markedly attenuates or completely blocks, reversibly, the subjective effects of intravenously administered opioids. When co-administered with morphine, on a chronic basis, naltrexone blocks the physical dependence to morphine, heroin and other opioids. In subjects physically dependent on opioids, naltrexone will precipitate withdrawal symptomatology.

Mechanism of action

Naltrexone is a pure opiate antagonist and has little or no agonist activity. The mechanism of action of naltrexone in alcoholism is not understood; however, involvement of the endogenous opioid system is suggested by preclinical data. Naltrexone is thought to act as a competitive antagonist at mc, κ, and δ receptors in the CNS, with the highest affintiy for the μ receptor. Naltrexone competitively binds to such receptors and may block the effects of endogenous opioids. This leads to the antagonization of most of the subjective and objective effects of opiates, including respiratory depression, miosis, euphoria, and drug craving. The major metabolite of naltrexone, 6-β-naltrexol, is also an opiate antagonist and may contribute to the antagonistic activity of the drug.

TargetActionsOrganism
ADelta-type opioid receptor
antagonist
Humans
AMu-type opioid receptor
antagonist
Humans
AKappa-type opioid receptor
antagonist
Humans
AHCG20471, isoform CRA_c
antagonist
Humans
Absorption

Although well absorbed orally, naltrexone is subject to significant first pass metabolism with oral bioavailability estimates ranging from 5 to 40%.

Volume of distribution
  • 1350 L [intravenous administration]
Protein binding

21% bound to plasma proteins over the therapeutic dose range.

Metabolism

Hepatic. When administered orally, naltrexone undergoes extensive biotransformation and is metabolized to 6 beta-naltrexol (which may contribute to the therapeutic effect) and other minor metabolites.

Hover over products below to view reaction partners

Route of elimination

Both parent drug and metabolites are excreted primarily by the kidney (53% to 79% of the dose), however, urinary excretion of unchanged naltrexone accounts for less than 2% of an oral dose and fecal excretion is a minor elimination pathway. The renal clearance for naltrexone ranges from 30 to 127 mL/min and suggests that renal elimination is primarily by glomerular filtration.

Half-life

4 hours for naltrexone and 13 hours for the active metabolite 6 beta-naltrexol.

Clearance
  • ~ 3.5 L/min [after IV administration]
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

In the mouse, rat and guinea pig, the oral LD50s were 1,100-1,550 mg/kg; 1,450 mg/kg; and 1,490 mg/kg; respectively. High doses of naltrexone (generally >1,000 mg/kg) produce salivation, depression/reduced activity, tremors, and convulsions.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Naltrexone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Mu-type opioid receptor---(A;G) / (G;G)A > GEffect Directly StudiedPatients with this genotype have an increased number of abstinent days when using naltrexone to treat alcohol addiction.Details

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
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Naltrexone.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Naltrexone.
AcipimoxThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Naltrexone is combined with Acipimox.
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Naltrexone.
AdenineThe metabolism of Naltrexone can be decreased when combined with Adenine.
Alendronic acidThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Naltrexone.
AlfentanilThe risk or severity of adverse effects can be increased when Naltrexone is combined with Alfentanil.
AlimemazineThe risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Naltrexone.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Naltrexone.
AlmotriptanThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with Almotriptan.
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
  • Take with or without food. The absorption is unaffected by food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Naltrexone hydrochlorideZ6375YW9SF16676-29-2RHBRMCOKKKZVRY-ITLPAZOVSA-N
Product Images
International/Other Brands
Abernil (Medochemie) / Adepend (AOP Orphan) / Antaxon (Zambon) / Antaxone (Pharmazam) / Arrop (Quimico) / Celupan / Depade / Dependex (Amomed) / Nalerona (ABL Pharma) / Nalorex (Bristol-Myers Squibb) / Naltax (Navana) / Naltrekson (Wyeth) / Narcoral (Sirton) / Neksi (GMP) / Nemexin (Bristol-Myers Squibb) / Opizone (Britannia) / Revez (Soubeiran Chobet) / Trexan (Du Pont) / Vivitrex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Addex-1000Pellet, implantable1000 mg/1SubcutaneousAdvanced Pharmaceutical Technology, Inc.2018-05-16Not applicableUS flag
Naltrexone Hydrochloride Tablets USPTabletOralSterinova Inc2017-05-30Not applicableCanada flag
ReviaTablet50 mgOralTEVA Canada Limited1997-10-23Not applicableCanada flag
Revia - Tab 50mgTabletOralDupont Merck Pharma Inc.1995-12-311998-08-13Canada flag
Vivitrol380 mg/4mLIntramuscularAlkermes, Inc.2006-06-13Not applicableUS flag
VivitrolKit380 mg/1IntramuscularCephalon2006-06-132009-12-31US flag
VivitrolKit380 mg/4mLIntramuscularAlkermes, Inc.2006-06-132015-12-08US flag
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 EndRegionImage
Apo-naltrexoneTabletOralApotex Corporation2015-11-10Not applicableCanada flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralUnit Dose Services1998-05-082017-08-31US flag00555 0902 02 nlmimage10 d01b687b
Naltrexone HydrochlorideTablet, film coated50 mg/1OralPrecision Dose Inc.2014-10-29Not applicableUS flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralA-S Medication Solutions2012-01-18Not applicableUS flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralAvera McKennan Hospital2016-02-102017-05-24US flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralNuCare Pharmaceuticls, Inc.2013-09-23Not applicableUS flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralAvKARE, Inc.2015-03-26Not applicableUS flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralREMEDYREPACK INC.2018-04-27Not applicableUS flag
Naltrexone HydrochlorideTablet, film coated50 mg/1OralPhysicians Total Care, Inc.2006-04-19Not applicableUS flag54868 557420180907 15195 1lmawi7
Naltrexone HydrochlorideTablet, film coated50 mg/1OralA-S Medication Solutions2013-09-23Not applicableUS flag
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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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ContraveNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, film coated, extended releaseOralTakeda Pharmaceuticals America, Inc.2014-09-102019-08-15US flag
ContraveNaltrexone hydrochloride (8 mg) + Bupropion hydrochloride (90 mg)Tablet, extended releaseOralBausch Health, Canada Inc.2018-03-16Not applicableCanada flag
ContraveNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, film coated, extended releaseOralA-S Medication Solutions2014-09-102018-09-30US flag
Contrave Extended-ReleaseNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, extended releaseOralPD-Rx Pharmaceuticals, Inc.2014-10-22Not applicableUS flag
Contrave Extended-ReleaseNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, extended releaseOralA-S Medication Solutions2014-10-22Not applicableUS flag
Contrave Extended-ReleaseNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, extended releaseOralNalpropion Pharmaceuticals LLC2014-10-22Not applicableUS flag
EmbedaNaltrexone hydrochloride (2 mg/1) + Morphine sulfate pentahydrate (50 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
EmbedaNaltrexone hydrochloride (.8 mg/1) + Morphine sulfate pentahydrate (20 mg/1)Capsule, extended releaseOralStat Rx USA2009-08-13Not applicableUS flag
EmbedaNaltrexone hydrochloride (3.2 mg/1) + Morphine sulfate pentahydrate (80 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
EmbedaNaltrexone hydrochloride (1.2 mg/1) + Morphine sulfate pentahydrate (30 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
NaltrexoneNaltrexone (200 mg/1) + Triamcinolone (6.5 mg/1)ImplantSubcutaneousComplete Pharmacy And Medical Solutions2018-02-01Not applicableUS flag

Categories

ATC Codes
N02AA56 — Oxycodone and naltrexoneN07BB04 — NaltrexoneA08AA62 — Bupropion and naltrexone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Not Available
Direct Parent
Phenanthrenes and derivatives
Alternative Parents
Isoquinolones and derivatives / Tetralins / Coumarans / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Aralkylamines / Piperidines / Tertiary alcohols / Trialkylamines / 1,2-aminoalcohols
show 7 more
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Coumaran
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, cyclopropanes, morphinane-like compound (CHEBI:7465)

Chemical Identifiers

UNII
5S6W795CQM
CAS number
16590-41-3
InChI Key
DQCKKXVULJGBQN-XFWGSAIBSA-N
InChI
InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1
IUPAC Name
(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
SMILES
[H][[email protected]@]12OC3=C(O)C=CC4=C3[[email protected]@]11CCN(CC3CC3)[[email protected]]([H])(C4)[[email protected]]1(O)CCC2=O

References

Synthesis Reference

Bao-Shan Huang, Yansong Lu, Ben-Yi Ji, Aris P Christodoulou, "Preparation of naltrexone from codeine and 3-benzylmorphine." U.S. Patent US6013796, issued March, 1990.

US6013796
General References
  1. Schmitz JM, Stotts AL, Rhoades HM, Grabowski J: Naltrexone and relapse prevention treatment for cocaine-dependent patients. Addict Behav. 2001 Mar-Apr;26(2):167-80. [PubMed:11316375]
  2. Krystal JH, Gueorguieva R, Cramer J, Collins J, Rosenheck R: Naltrexone is associated with reduced drinking by alcohol dependent patients receiving antidepressants for mood and anxiety symptoms: results from VA Cooperative Study No. 425, "Naltrexone in the treatment of alcoholism". Alcohol Clin Exp Res. 2008 Jan;32(1):85-91. Epub 2007 Dec 7. [PubMed:18070245]
  3. Ray LA, Chin PF, Miotto K: Naltrexone for the treatment of alcoholism: clinical findings, mechanisms of action, and pharmacogenetics. CNS Neurol Disord Drug Targets. 2010 Mar;9(1):13-22. [PubMed:20201811]
  4. Kariv R, Tiomny E, Grenshpon R, Dekel R, Waisman G, Ringel Y, Halpern Z: Low-dose naltreoxone for the treatment of irritable bowel syndrome: a pilot study. Dig Dis Sci. 2006 Dec;51(12):2128-33. Epub 2006 Nov 1. [PubMed:17080248]
Human Metabolome Database
HMDB0014842
KEGG Drug
D05113
KEGG Compound
C07253
PubChem Compound
5360515
PubChem Substance
46505333
ChemSpider
4514524
BindingDB
60212
RxNav
7243
ChEBI
7465
ChEMBL
CHEMBL19019
ZINC
ZINC000000001773
Therapeutic Targets Database
DAP000379
PharmGKB
PA450588
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Naltrexone
AHFS Codes
  • 28:10.00 — Opiate Antagonists
FDA label
Download (1.83 MB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAlcohol Dependence / Alcohol Use Disorder (AUD)1
4Active Not RecruitingTreatmentAlcohol Dependence / Alcohol Use Disorder (AUD) / Heavy Drinking1
4Active Not RecruitingTreatmentBMI >30 kg/m21
4Active Not RecruitingTreatmentHeroin Dependence / Opioid Dependence1
4Active Not RecruitingTreatmentHeroin Dependence / Opioid-Related Disorders1
4CompletedBasic ScienceAttention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder / Healthy Volunteers1
4CompletedBasic ScienceDepression / Major Depressive Disorder (MDD)1
4CompletedBasic ScienceHeroin Dependence / Opioid-Related Disorders1
4CompletedBasic ScienceNeuroscience of Dreaming, Healthy1
4CompletedDiagnosticHealthy Volunteers1

Pharmacoeconomics

Manufacturers
  • Alkermes inc
  • Actavis totowa llc
  • Barr laboratories inc
  • Mallinckrodt inc
  • Sandoz inc
  • Duramed pharmaceuticals inc
Packagers
  • Alkermes Inc.
  • Barr Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Cephalon Inc.
  • D.M. Graham Laboratories Inc.
  • Duramed
  • Eon Labs
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • King Pharmaceuticals Inc.
  • Mallinckrodt Inc.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Professional Co.
  • Spectrum Pharmaceuticals
  • Stat Rx Usa
Dosage Forms
FormRouteStrength
Pellet, implantableSubcutaneous1000 mg/1
Capsule10 MG
Capsule25 MG
Capsule50 MG
SolutionOral100 MG/20ML
SolutionOral50 MG/10ML
SolutionOral50 MG
Tablet, film coated, extended releaseOral
Tablet, film coatedOral50 mg
Capsule, extended releaseOral
Tablet, film coated50 mg
Tablet, extended releaseOral8 MG
ImplantSubcutaneous
Tablet, coatedOral50 MG
PowderNot applicable1 g/1g
Tablet, film coatedOral50 mg/1
Tablet, extended releaseOral
Tablet
TabletOral10 MG
TabletOral50 MG
TabletOral
KitIntramuscular380 mg/4mL
KitIntramuscular380 mg/1
Prices
Unit descriptionCostUnit
Vivitrol injectable suspension960.0USD each
ReVia 30 50 mg tablet Bottle291.73USD bottle
Naltrexone hcl powder172.54USD g
Naltrexone powder69.0USD g
Revia 50 mg tablet9.35USD tablet
Naltrexone 50 mg tablet4.57USD tablet
Naltrexone HCl 50 mg tablet4.45USD tablet
Depade 50 mg tablet4.28USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7919499No2011-04-052029-10-15US flag
US6537586No2003-03-252019-11-12US flag
US6331317No2001-12-182019-11-12US flag
US6667061Yes2003-12-232020-11-25US flag
US5792477Yes1998-08-112017-11-02US flag
US6395304No2002-05-282019-11-12US flag
US7799345No2010-09-212020-05-25US flag
US5916598Yes1999-06-292017-11-02US flag
US6379703Yes2002-04-302019-06-30US flag
US6495164No2002-12-172020-05-25US flag
US6403114Yes2002-06-112017-11-02US flag
US6379704No2002-04-302020-05-19US flag
US6596316Yes2003-07-222019-06-30US flag
US6713090No2004-03-302019-11-12US flag
US6194006Yes2001-02-272019-06-30US flag
US6264987No2001-07-242020-05-19US flag
US6495166No2002-12-172019-11-12US flag
US6534092No2003-03-182020-05-19US flag
US6939033No2005-09-062019-11-12US flag
US8685443No2014-04-012025-07-03US flag
US8158156No2012-04-172027-06-19US flag
US7682633No2010-03-232027-06-19US flag
US8623418No2014-01-072029-11-07US flag
US8685444No2014-04-012025-07-03US flag
US8846104No2014-09-302027-06-19US flag
US7815934No2010-10-192027-12-12US flag
US7682634No2010-03-232027-06-19US flag
US8877247No2014-11-042027-06-19US flag
US8722085No2014-05-132027-11-08US flag
US8318788No2012-11-272027-11-08US flag
US7462626No2008-12-092024-07-20US flag
US8815889No2014-08-262024-07-20US flag
US9107837No2015-08-182027-06-04US flag
US9125868No2015-09-082027-11-08US flag
US8916195No2014-12-232030-02-02US flag
US9248123No2016-02-022032-01-13US flag
US8088786No2012-01-032029-02-03US flag
US7375111No2008-05-202025-03-26US flag
US10231964No2019-03-192034-07-02US flag
US10307376No2019-06-042027-11-08US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168-170 °CPhysProp
water solubility100 mg/mL (as hydrochloride salt)Not Available
logP1.92HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.07 mg/mLALOGPS
logP2.07ALOGPS
logP1.36ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)7.39ChemAxon
pKa (Strongest Basic)11.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.5 m3·mol-1ChemAxon
Polarizability35.97 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9769
Blood Brain Barrier+0.9671
Caco-2 permeable+0.7471
P-glycoprotein substrateSubstrate0.8685
P-glycoprotein inhibitor INon-inhibitor0.8867
P-glycoprotein inhibitor IINon-inhibitor0.8718
Renal organic cation transporterNon-inhibitor0.5189
CYP450 2C9 substrateNon-substrate0.8336
CYP450 2D6 substrateSubstrate0.5925
CYP450 3A4 substrateSubstrate0.5981
CYP450 1A2 substrateInhibitor0.6656
CYP450 2C9 inhibitorNon-inhibitor0.9355
CYP450 2D6 inhibitorNon-inhibitor0.5686
CYP450 2C19 inhibitorNon-inhibitor0.9354
CYP450 3A4 inhibitorNon-inhibitor0.8993
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9483
Ames testNon AMES toxic0.6324
CarcinogenicityNon-carcinogens0.96
BiodegradationNot ready biodegradable0.9939
Rat acute toxicity2.7174 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.861
hERG inhibition (predictor II)Non-inhibitor0.8446
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
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 , positiveLC-MS/MSsplash10-00di-0009000000-e30316dd5784a7100d38
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0009000000-2218214724e56047d52b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0009000000-bb047c719f3429eb4410
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0049000000-de9a717563978f22f02f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00xr-0191000000-d2f2ff1e4eb93db46b5e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-1390000000-091705f6f42bc0f1c209
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-1890000000-148c5608ef92c1dcaac4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0009000000-6df03abdbdb7461f2945
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0009000000-059b1dffee7ef15b9e95
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0049000000-a20ede951b350fa97a31
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00xr-0191000000-8a66ac92b4a1eadcc405
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-1490000000-0cfb621f77295ff438f2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-1980000000-63edda852273619df16c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-59ab0ef68d6e13a7d085

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Roy S, Guo X, Kelschenbach J, Liu Y, Loh HH: In vivo activation of a mutant mu-opioid receptor by naltrexone produces a potent analgesic effect but no tolerance: role of mu-receptor activation and delta-receptor blockade in morphine tolerance. J Neurosci. 2005 Mar 23;25(12):3229-33. [PubMed:15788780]
  3. Barrios de Tomasi E, Juarez-Gonzalez J: [Opioid antagonists and alcohol consumption]. Rev Neurol. 2007 Aug 1-15;45(3):155-62. [PubMed:17661275]
  4. Weerts EM, Kim YK, Wand GS, Dannals RF, Lee JS, Frost JJ, McCaul ME: Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects. Neuropsychopharmacology. 2008 Feb;33(3):653-65. Epub 2007 May 9. [PubMed:17487229]
  5. Herz A: Opioid reward mechanisms: a key role in drug abuse? Can J Physiol Pharmacol. 1998 Mar;76(3):252-8. [PubMed:9673788]
  6. Herz A: Endogenous opioid systems and alcohol addiction. Psychopharmacology (Berl). 1997 Jan;129(2):99-111. [PubMed:9040115]
Details
2. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Kato H: [Pharmacological effects of a mu-opioid receptor antagonist naltrexone on alcohol dependence]. Nihon Arukoru Yakubutsu Igakkai Zasshi. 2008 Oct;43(5):697-704. [PubMed:19068776]
  3. Helm S, Trescot AM, Colson J, Sehgal N, Silverman S: Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician. 2008 Mar-Apr;11(2):225-35. [PubMed:18354714]
  4. Goodman AJ, Le Bourdonnec B, Dolle RE: Mu opioid receptor antagonists: recent developments. ChemMedChem. 2007 Nov;2(11):1552-70. [PubMed:17918759]
  5. Barrios de Tomasi E, Juarez-Gonzalez J: [Opioid antagonists and alcohol consumption]. Rev Neurol. 2007 Aug 1-15;45(3):155-62. [PubMed:17661275]
  6. Weerts EM, Kim YK, Wand GS, Dannals RF, Lee JS, Frost JJ, McCaul ME: Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects. Neuropsychopharmacology. 2008 Feb;33(3):653-65. Epub 2007 May 9. [PubMed:17487229]
  7. Herz A: Opioid reward mechanisms: a key role in drug abuse? Can J Physiol Pharmacol. 1998 Mar;76(3):252-8. [PubMed:9673788]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Helm S, Trescot AM, Colson J, Sehgal N, Silverman S: Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician. 2008 Mar-Apr;11(2):225-35. [PubMed:18354714]
  3. Herz A: Endogenous opioid systems and alcohol addiction. Psychopharmacology (Berl). 1997 Jan;129(2):99-111. [PubMed:9040115]
  4. Barrios de Tomasi E, Juarez-Gonzalez J: [Opioid antagonists and alcohol consumption]. Rev Neurol. 2007 Aug 1-15;45(3):155-62. [PubMed:17661275]
  5. Wee S, Orio L, Ghirmai S, Cashman JR, Koob GF: Inhibition of kappa opioid receptors attenuated increased cocaine intake in rats with extended access to cocaine. Psychopharmacology (Berl). 2009 Sep;205(4):565-75. doi: 10.1007/s00213-009-1563-y. Epub 2009 May 30. [PubMed:19484223]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Not Available
Specific Function
Not Available
Gene Name
SIGMAR1
Uniprot ID
Q5T1J1
Uniprot Name
HCG20471, isoform CRA_c
Molecular Weight
14852.655 Da
References
  1. Helm S, Trescot AM, Colson J, Sehgal N, Silverman S: Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician. 2008 Mar-Apr;11(2):225-35. [PubMed:18354714]
  2. Wee S, Orio L, Ghirmai S, Cashman JR, Koob GF: Inhibition of kappa opioid receptors attenuated increased cocaine intake in rats with extended access to cocaine. Psychopharmacology (Berl). 2009 Sep;205(4):565-75. doi: 10.1007/s00213-009-1563-y. Epub 2009 May 30. [PubMed:19484223]
  3. Herz A: Endogenous opioid systems and alcohol addiction. Psychopharmacology (Berl). 1997 Jan;129(2):99-111. [PubMed:9040115]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Antonilli L, Brusadin V, Milella MS, Sobrero F, Badiani A, Nencini P: In vivo chronic exposure to heroin or naltrexone selectively inhibits liver microsome formation of estradiol-3-glucuronide in the rat. Biochem Pharmacol. 2008 Sep 1;76(5):672-9. doi: 10.1016/j.bcp.2008.06.011. Epub 2008 Jul 1. [PubMed:18639530]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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