Naltrexone

Identification

Summary

Naltrexone is a narcotic antagonist used in opioid overdose.

Brand Names

Contrave, Embeda, Vivitrol

Generic Name

Naltrexone

DrugBank Accession Number

DB00704

Background

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Naltrexone (DB00704)

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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

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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.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Alcohol dependence		••••••••••••
Management of	Cholestatic pruritus		••• •••••	•••••
Used as adjunct in combination to treat	Obesity	Combination Product in combination with: Bupropion (DB01156)	••••••••••••			••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• •••••••
Used as adjunct in combination to manage	Obesity	Combination Product in combination with: Bupropion (DB01156)	••••••••••••		••••••••••• •• •••••••••••••• •••••••••••	••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• •••••••
Used as adjunct in combination to treat	Obesity	Combination Product in combination with: Bupropion (DB01156)	••••••••••••		•• •••••••••••••• •••••••••••	••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• •••••••

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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.

Target	Actions	Organism
AMu-type opioid receptor	antagonist	Humans
AKappa-type opioid receptor	antagonist	Humans
ADelta-type opioid receptor	antagonist	Humans
USigma non-opioid intracellular receptor 1	Not Available	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

• Naltrexone
  • 6-beta-naltrexol

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

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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.

Pathways

Pathway	Category
Naltrexone Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Mu-type opioid receptor	---	(G;G) / (A;G)	A > G	Effect Directly Studied	Patients with this genotype have an increased number of abstinent days when using naltrexone to treat alcohol addiction.	Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when Naltrexone is combined with 1,2-Benzodiazepine.
Acamprosate	The bioavailability of Acamprosate can be increased when combined with Naltrexone.
Acetazolamide	The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Naltrexone.
Acetophenazine	The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Naltrexone.
Acipimox	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Naltrexone is combined with Acipimox.

Food Interactions

• Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Naltrexone hydrochloride	Z6375YW9SF	16676-29-2	RHBRMCOKKKZVRY-ITLPAZOVSA-N

Product Images

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Addex-1000	Pellet, implantable	1000 mg/1	Subcutaneous	Advanced Pharmaceutical Technology, Inc.	2018-05-16	Not applicable
Naltrexone Hydrochloride Tablets USP	Tablet	50 mg	Oral	Sterinova Inc.	2017-05-30	Not applicable
Revia	Tablet	50 mg	Oral	TEVA Canada Limited	1997-10-23	Not applicable
Revia - Tab 50mg	Tablet	50 mg / tab	Oral	Dupont Merck Pharma Inc.	1995-12-31	1998-08-13
Vivitrol	Injection, powder, for suspension, extended release; Kit	380 mg/4mL	Intramuscular	Alkermes, Inc.	2006-06-13	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-naltrexone	Tablet	50 mg	Oral	Apotex Corporation	2015-11-10	Not applicable
Naltrexone Hydrochloride	Tablet, film coated	50 mg/1	Oral	A-S Medication Solutions	2012-01-18	Not applicable
Naltrexone Hydrochloride	Tablet, film coated	50 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	1998-05-08	2017-08-31
Naltrexone Hydrochloride	Tablet, film coated	50 mg/1	Oral	REMEDYREPACK INC.	2018-04-27	Not applicable
Naltrexone Hydrochloride	Tablet, film coated	50 mg/1	Oral	Chartwell Rx, Llc	2017-07-21	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Contrave	Naltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)	Tablet, film coated, extended release	Oral	Takeda Pharmaceuticals America, Inc.	2014-09-10	2019-08-15
Contrave	Naltrexone hydrochloride (8 mg) + Bupropion hydrochloride (90 mg)	Tablet, extended release	Oral	Bausch Health, Canada Inc.	2018-03-16	Not applicable
Contrave	Naltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)	Tablet, film coated, extended release	Oral	A-S Medication Solutions	2014-09-10	2018-09-30
Contrave Extended-Release	Naltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)	Tablet, extended release	Oral	Nalpropion Pharmaceuticals LLC	2014-10-22	Not applicable
Contrave Extended-Release	Naltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)	Tablet, extended release	Oral	A-S Medication Solutions	2014-10-22	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Naltrexone	Naltrexone (200 mg/1) + Triamcinolone (6.5 mg/1)	Implant	Subcutaneous	Complete Pharmacy And Medical Solutions	2018-02-01	Not applicable

Categories

ATC Codes

N02AA56 — Oxycodone and naltrexone

• N02AA — Natural opium alkaloids
• N02A — OPIOIDS
• N02 — ANALGESICS
• N — NERVOUS SYSTEM

N07BB04 — Naltrexone

• N07BB — Drugs used in alcohol dependence
• N07B — DRUGS USED IN ADDICTIVE DISORDERS
• N07 — OTHER NERVOUS SYSTEM DRUGS
• N — NERVOUS SYSTEM

A08AA62 — Bupropion and naltrexone

• A08AA — Centrally acting antiobesity products
• A08A — ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
• A08 — ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Agents Causing Muscle Toxicity
• Alcohol Deterrents
• Alimentary Tract and Metabolism
• Alkaloids
• Analgesics
• Antiobesity Preparations, Excl. Diet Products
• Central Nervous System Agents
• Centrally Acting Antiobesity Products
• Drugs Used in Addictive Disorders
• Drugs Used in Alcohol Dependence
• Heterocyclic Compounds, Fused-Ring
• Morphinans
• Natural Opium Alkaloids
• Nervous System
• Opiate Alkaloids
• Opiate Antagonists
• Opioid Antagonists
• Opioids
• Peripheral Nervous System Agents
• Phenanthrenes
• Sensory System Agents
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
• UGT1A1 Substrates

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 / Ketones / Cyclic alcohols and derivatives / Oxacyclic compounds / Azacyclic compounds / Organic oxides / Hydrocarbon derivatives / Organopnictogen compounds

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 / Cyclic alcohol / Ether / Hydrocarbon derivative / Isoquinolone / Ketone / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Phenanthrene / Piperidine / Tertiary alcohol / Tertiary aliphatic amine / Tertiary amine / Tetralin

show 19 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound, cyclopropanes, morphinane-like compound (CHEBI:7465)

Affected organisms

• Humans and other mammals

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[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC3CC3)[C@]([H])(C4)[C@]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. [Article]
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. [Article]
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. [Article]
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. [Article]

External Links

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

FDA label

Download (1.83 MB)

MSDS

Download (73.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Obesity	3
4	Active Not Recruiting	Treatment	Obesity / Type 2 Diabetes Mellitus	1
4	Completed	Basic Science	Attention Deficit Hyperactivity Disorder (ADHD) / Healthy Subjects (HS)	1
4	Completed	Basic Science	Depression / Major Depressive Disorder (MDD)	1
4	Completed	Basic Science	Heroin Dependence / Opioid Related Disorders	1

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

Form	Route	Strength
Pellet, implantable	Subcutaneous	1000 mg/1
Capsule	Oral	10 MG
Capsule	Oral	25 MG
Capsule	Oral	50 MG
Solution	Oral	100 MG/20ML
Solution	Oral	50 MG/10ML
Solution	Oral	50 MG
Tablet	Oral	50.000 mg
Tablet, film coated, extended release	Oral
Capsule, extended release	Oral
Tablet	Oral
Tablet, coated	Oral	50 MG
Tablet, film coated	Oral
Implant	Subcutaneous
Tablet, film coated	Oral	50 MG
Powder	Not applicable	1 g/1g
Tablet, film coated	Oral	50 mg/1
Tablet, extended release	Oral
Tablet	Oral
Tablet	Oral	10 MG
Tablet	Oral	50 mg
Tablet	Oral	50 mg / tab
Injection, powder, for suspension, extended release; kit	Intramuscular	380 mg/4mL
Kit	Intramuscular	380 mg/1

Prices

Unit description	Cost	Unit
Vivitrol injectable suspension	960.0USD	each
ReVia 30 50 mg tablet Bottle	291.73USD	bottle
Naltrexone hcl powder	172.54USD	g
Naltrexone powder	69.0USD	g
Revia 50 mg tablet	9.35USD	tablet
Naltrexone 50 mg tablet	4.57USD	tablet
Naltrexone HCl 50 mg tablet	4.45USD	tablet
Depade 50 mg tablet	4.28USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7919499	No	2011-04-05	2029-10-15
US6537586	No	2003-03-25	2019-11-12
US6331317	No	2001-12-18	2019-11-12
US6667061	Yes	2003-12-23	2020-11-25
US5792477	Yes	1998-08-11	2017-11-02
US6395304	No	2002-05-28	2019-11-12
US7799345	No	2010-09-21	2020-05-25
US5916598	Yes	1999-06-29	2017-11-02
US6379703	Yes	2002-04-30	2019-06-30
US6495164	No	2002-12-17	2020-05-25
US6403114	Yes	2002-06-11	2017-11-02
US6379704	No	2002-04-30	2020-05-19
US6596316	Yes	2003-07-22	2019-06-30
US6713090	No	2004-03-30	2019-11-12
US6194006	Yes	2001-02-27	2019-06-30
US6264987	No	2001-07-24	2020-05-19
US6495166	No	2002-12-17	2019-11-12
US6534092	No	2003-03-18	2020-05-19
US6939033	No	2005-09-06	2019-11-12
US8685443	No	2014-04-01	2025-07-03
US8158156	No	2012-04-17	2027-06-19
US7682633	No	2010-03-23	2027-06-19
US8623418	No	2014-01-07	2029-11-07
US8685444	No	2014-04-01	2025-07-03
US8846104	No	2014-09-30	2027-06-19
US7815934	No	2010-10-19	2027-12-12
US7682634	No	2010-03-23	2027-06-19
US8877247	No	2014-11-04	2027-06-19
US8722085	No	2014-05-13	2027-11-08
US8318788	No	2012-11-27	2027-11-08
US7462626	No	2008-12-09	2024-07-20
US8815889	No	2014-08-26	2024-07-20
US9107837	No	2015-08-18	2027-06-04
US9125868	No	2015-09-08	2027-11-08
US8916195	No	2014-12-23	2030-02-02
US9248123	No	2016-02-02	2032-01-13
US8088786	No	2012-01-03	2029-02-03
US7375111	No	2008-05-20	2025-03-26
US10231964	No	2019-03-19	2034-07-02
US10307376	No	2019-06-04	2027-11-08
US10835527	No	2020-11-17	2034-07-02
US10828294	No	2020-11-10	2034-07-02
US11139056	No	2021-10-05	2033-06-05
US10403170	No	2019-09-03	2033-06-05
US9633575	No	2017-04-25	2033-06-25
US11033543	No	2021-06-15	2031-01-10
US11278544	No	2004-04-21	2024-04-21
US11324741	No	2009-05-29	2029-05-29

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	168-170 °C	PhysProp
water solubility	100 mg/mL (as hydrochloride salt)	Not Available
logP	1.92	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	3.07 mg/mL	ALOGPS
logP	2.07	ALOGPS
logP	1.27	Chemaxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.2	Chemaxon
pKa (Strongest Basic)	9.35	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	70 Å2	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	91.5 m3·mol-1	Chemaxon
Polarizability	36.03 Å3	Chemaxon
Number of Rings	6	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9769
Blood Brain Barrier	+	0.9671
Caco-2 permeable	+	0.7471
P-glycoprotein substrate	Substrate	0.8685
P-glycoprotein inhibitor I	Non-inhibitor	0.8867
P-glycoprotein inhibitor II	Non-inhibitor	0.8718
Renal organic cation transporter	Non-inhibitor	0.5189
CYP450 2C9 substrate	Non-substrate	0.8336
CYP450 2D6 substrate	Substrate	0.5925
CYP450 3A4 substrate	Substrate	0.5981
CYP450 1A2 substrate	Inhibitor	0.6656
CYP450 2C9 inhibitor	Non-inhibitor	0.9355
CYP450 2D6 inhibitor	Non-inhibitor	0.5686
CYP450 2C19 inhibitor	Non-inhibitor	0.9354
CYP450 3A4 inhibitor	Non-inhibitor	0.8993
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9483
Ames test	Non AMES toxic	0.6324
Carcinogenicity	Non-carcinogens	0.96
Biodegradation	Not ready biodegradable	0.9939
Rat acute toxicity	2.7174 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.861
hERG inhibition (predictor II)	Non-inhibitor	0.8446

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4l-9032000000-f869731a6a6d2ba21fc9
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0009000000-e30316dd5784a7100d38
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-0009000000-2218214724e56047d52b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-0009000000-bb047c719f3429eb4410
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0049000000-de9a717563978f22f02f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00xr-0191000000-d2f2ff1e4eb93db46b5e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-1390000000-091705f6f42bc0f1c209
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-1890000000-148c5608ef92c1dcaac4
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-0009000000-6df03abdbdb7461f2945
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-0009000000-059b1dffee7ef15b9e95
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0049000000-a20ede951b350fa97a31
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00xr-0191000000-8a66ac92b4a1eadcc405
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-1490000000-0cfb621f77295ff438f2
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-1980000000-63edda852273619df16c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0009000000-59ab0ef68d6e13a7d085
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-d957cbfc80e383cfdcb2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-ebe85c72152e0991d0ac
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00dl-0009000000-135f39da015b6e80290f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-3b8eacce8ef31b26c44b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0036-1069000000-a8eac039b51f4af9959e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000y-0097000000-ff22d58600abeaa790ad
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	185.0978335	predicted	DarkChem Lite v0.1.0
[M-H]-	185.2552335	predicted	DarkChem Lite v0.1.0
[M-H]-	184.72047	predicted	DeepCCS 1.0 (2019)
[M+H]+	184.8287335	predicted	DarkChem Lite v0.1.0
[M+H]+	185.4879335	predicted	DarkChem Lite v0.1.0
[M+H]+	187.13283	predicted	DeepCCS 1.0 (2019)
[M+Na]+	184.7870335	predicted	DarkChem Lite v0.1.0
[M+Na]+	184.8500335	predicted	DarkChem Lite v0.1.0
[M+Na]+	194.87132	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2	N/A	N/A	A28815

Details

Binding Properties1. 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. [Article]
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. [Article]
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. [Article]
4. Goodman AJ, Le Bourdonnec B, Dolle RE: Mu opioid receptor antagonists: recent developments. ChemMedChem. 2007 Nov;2(11):1552-70. [Article]
5. Barrios de Tomasi E, Juarez-Gonzalez J: [Opioid antagonists and alcohol consumption]. Rev Neurol. 2007 Aug 1-15;45(3):155-62. [Article]
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. [Article]
7. Herz A: Opioid reward mechanisms: a key role in drug abuse? Can J Physiol Pharmacol. 1998 Mar;76(3):252-8. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	10	N/A	N/A	A28815

Details

Binding Properties2. Kappa-type opioid receptor

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. [Article]
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. [Article]
3. Herz A: Endogenous opioid systems and alcohol addiction. Psychopharmacology (Berl). 1997 Jan;129(2):99-111. [Article]
4. Barrios de Tomasi E, Juarez-Gonzalez J: [Opioid antagonists and alcohol consumption]. Rev Neurol. 2007 Aug 1-15;45(3):155-62. [Article]
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. [Article]

Details3. Delta-type opioid receptor

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. [Article]
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. [Article]
3. Barrios de Tomasi E, Juarez-Gonzalez J: [Opioid antagonists and alcohol consumption]. Rev Neurol. 2007 Aug 1-15;45(3):155-62. [Article]
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. [Article]
5. Herz A: Opioid reward mechanisms: a key role in drug abuse? Can J Physiol Pharmacol. 1998 Mar;76(3):252-8. [Article]
6. Herz A: Endogenous opioid systems and alcohol addiction. Psychopharmacology (Berl). 1997 Jan;129(2):99-111. [Article]

Details4. Sigma non-opioid intracellular receptor 1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Opioid receptor activity

Specific Function

Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...

Gene Name

SIGMAR1

Uniprot ID

Q99720

Uniprot Name

Sigma non-opioid intracellular receptor 1

Molecular Weight

25127.52 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. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55