Identification

Name
Naltrexone
Accession Number
DB00704  (APRD00005, DB05067)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Naltrexone hydrochlorideZ6375YW9SF16676-29-2RHBRMCOKKKZVRY-ITLPAZOVSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naltrexone Hydrochloride Tablets USPTablet50 mgOralSterinova Inc2017-05-30Not applicableCanada
ReviaTablet50 mgOralTeva1997-10-23Not applicableCanada
Revia - Tab 50mgTablet50 mgOralDupont Merck Pharma Inc.1995-12-311998-08-13Canada
VivitrolKit380 mg/1Cephalon2006-06-132009-12-31Us
VivitrolKit380 mg/4mLAlkermes, Inc.2006-06-13Not applicableUs
VivitrolKit380 mg/4mLAlkermes, Inc.2006-06-132015-12-08Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-naltrexoneTablet50 mgOralApotex Corporation2015-11-10Not applicableCanada
Naltrexone HydrochlorideTablet, film coated50 mg/1OralRemedy Repack2018-04-27Not applicableUs
Naltrexone HydrochlorideTablet, film coated50 mg/1OralAidarex Pharmaceuticals LLC2013-09-23Not applicableUs
Naltrexone HydrochlorideTablet, film coated50 mg/1OralSun Pharmaceutical Industries, Inc.2012-02-29Not applicableUs
Naltrexone HydrochlorideTablet, film coated50 mg/1OralAvera McKennan Hospital2016-02-102018-06-11Us
Naltrexone HydrochlorideTablet, film coated50 mg/1Oralbryant ranch prepack1998-05-08Not applicableUs63629 530420180907 15195 pak1ma
Naltrexone HydrochlorideTablet, film coated50 mg/1OralPd Rx Pharmaceuticals, Inc.1998-05-082017-08-31Us
Naltrexone HydrochlorideTablet, film coated50 mg/1OralRemedy Repack2018-07-19Not applicableUs
Naltrexone HydrochlorideTablet, film coated50 mg/1OralUnit Dose Services1998-05-082017-08-31Us00555 0902 02 nlmimage10 d01b687b
Naltrexone HydrochlorideTablet, film coated50 mg/1OralSpecGx LLC2009-07-29Not applicableUs00406 1170 03 nlmimage10 af08d7e6
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ContraveNaltrexone hydrochloride (8 mg) + Bupropion hydrochloride (90 mg)Tablet, extended releaseOralValeant Canada Lp Valeant Canada S.E.C.2018-03-16Not applicableCanada
ContraveNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, film coated, extended releaseOralA-S Medication Solutions2014-09-10Not applicableUs
ContraveNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, film coated, extended releaseOralTakeda2014-09-10Not applicableUs
Contrave Extended-ReleaseNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, extended releaseOralNalpropion Pharmaceuticals, Inc.2014-10-22Not applicableUs
Contrave Extended-ReleaseNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, extended releaseOralPD-Rx Pharmaceuticals, Inc.2014-10-22Not applicableUs
Contrave Extended-ReleaseNaltrexone hydrochloride (8 mg/1) + Bupropion hydrochloride (90 mg/1)Tablet, extended releaseOralA-S Medication Solutions2014-09-10Not applicableUs
EmbedaNaltrexone hydrochloride (2 mg/1) + Morphine sulfate pentahydrate (50 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUs
EmbedaNaltrexone hydrochloride (3.2 mg/1) + Morphine sulfate pentahydrate (80 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUs
EmbedaNaltrexone hydrochloride (1.2 mg/1) + Morphine sulfate pentahydrate (30 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUs
EmbedaNaltrexone hydrochloride (2.4 mg/1) + Morphine sulfate pentahydrate (60 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
NaltrexoneNaltrexone (200 mg/1) + Triamcinolone (6.5 mg/1)ImplantSubcutaneousComplete Pharmacy And Medical Solutions2018-02-01Not applicableUs
International/Other Brands
Abernil (Medochemie) / Adepend (AOP Orphan) / Antaxon (Zambon) / Antaxone (Pharmazam) / Arrop (Quimico) / Celupan / Depade / Dependex (Amomed) / MorViva / 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
Categories
UNII
5S6W795CQM
CAS number
16590-41-3
Weight
Average: 341.4009
Monoisotopic: 341.162708229
Chemical Formula
C20H23NO4
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][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC3CC3)[C@]([H])(C4)[C@]1(O)CCC2=O

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
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
Human
AMu-type opioid receptor
antagonist
Human
AKappa-type opioid receptor
antagonist
Human
AHCG20471, isoform CRA_c
antagonist
Human
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.

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]
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---(G;G) / (A;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
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with 4-Bromo-2,5-dimethoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with 5-methoxy-N,N-dimethyltryptamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Naltrexone is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of hypotension and central nervous system depression can be increased when Acepromazine is combined with Naltrexone.
AceprometazineThe risk or severity of hypotension and central nervous system depression can be increased when Aceprometazine is combined with Naltrexone.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Naltrexone.
AcetophenazineThe risk or severity of hypotension and central nervous system depression can be increased when Acetophenazine is combined with Naltrexone.
Food Interactions
  • Take without regard to meals.

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]
External Links
Human Metabolome Database
HMDB0014842
KEGG Drug
D05113
KEGG Compound
C07253
PubChem Compound
5360515
PubChem Substance
46505333
ChemSpider
4514524
BindingDB
50000787
ChEBI
7465
ChEMBL
CHEMBL19019
Therapeutic Targets Database
DAP000379
PharmGKB
PA450588
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Naltrexone
ATC Codes
A08AA62 — Bupropion and naltrexoneN07BB04 — Naltrexone
AHFS Codes
  • 28:10.00 — Opiate Antagonists
FDA label
Download (1.83 MB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAlcohol Dependence1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailablePostoperative pain1
1CompletedBasic ScienceAlcohol Dependence1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceNondependent Opioid Abuse, Episodic1
1CompletedDiagnosticMethamphetamine Dependence1
1CompletedSupportive CarePsychotic Disorder NOS / Schizophrenic Disorders1
1CompletedTreatmentAlcohol Dependence2
1CompletedTreatmentAlcohol Drinking1
1CompletedTreatmentDepression1
1CompletedTreatmentECG Effects1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentOpioid Dependence1
1CompletedTreatmentOpioid Dependence / Opioid Use Disorders1
1CompletedTreatmentOpioid-Related Disorders1
1CompletedTreatmentOpioid-use Disorder1
1CompletedTreatmentPain NOS1
1RecruitingTreatmentCutaneous Nerves CNS Itch1
1RecruitingTreatmentGambling1
1, 2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Opioid Dependence / Substance, Addiction1
1, 2CompletedTreatmentAlcohol Dependence / Bipolar Disorder (BD)1
1, 2CompletedTreatmentCannabis Dependence1
1, 2CompletedTreatmentDiabetes, Diabetes Mellitus Type 1 / Hypoglycemia Unawareness1
1, 2CompletedTreatmentNicotine Dependence / Smoking2
1, 2CompletedTreatmentStable Opioid Dependence1
1, 2RecruitingTreatmentAlcohol Abuse / Alcohol Dependence / Alcohol Drinking / Alcohol Use Disorders (AUD) / Alcohol-Related Disorders1
1, 2RecruitingTreatmentAlcohol Use Disorder (AUD) / Major Depressive Disorder (MDD)1
1, 2RecruitingTreatmentAlcohol Use / Human Immunodeficiency Virus (HIV) Infections / Pain NOS1
1, 2Unknown StatusTreatmentPervasive Developmental Disorder NOS1
2Active Not RecruitingSupportive CareCarcinoma, Lobular / Ductal Carcinoma In Situ / Fatigue Related to Cancer Treatment / Invasive Breast Cancer (Stage I-III) / Lobular Carcinoma in Situ (LCIS)1
2Active Not RecruitingTreatmentOpioid Dependence1
2CompletedNot AvailableAlcohol Dependence1
2CompletedNot AvailableTobacco Dependence1
2CompletedBasic ScienceMarijuana Dependence1
2CompletedBasic ScienceSmoking, Marijuana1
2CompletedOtherAlcohol Drinking1
2CompletedPreventionAlcohols / Methamphetamine1
2CompletedPreventionHIV Seropositivity1
2CompletedPreventionOpiate Addiction1
2CompletedTreatmentAlcohol Abuse / Alcohol Dependence1
2CompletedTreatmentAlcohol Dependence5
2CompletedTreatmentAlcohol Dependence / Alcohol-Related Disorders / Cocaine-Related Disorders2
2CompletedTreatmentAlcohol Dependence / Dependence, Cocaine2
2CompletedTreatmentAlcohol Dependence / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentAlcohol Use Disorder (AUD)1
2CompletedTreatmentAlcohol Use Disorder (AUD) / Major Depressive Disorder (MDD)1
2CompletedTreatmentAlcohol-Related Disorders / Cocaine-Related Disorders1
2CompletedTreatmentAmphetamine-Related Disorders1
2CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m2 / Nicotine Dependence1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentBinge Drinking1
2CompletedTreatmentBorderline Personality Disorder (BPD) / Dissociation1
2CompletedTreatmentCessation, Smoking / Smoking1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCompulsive sexual behaviour1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentCrohn's Disease (CD) / Inflammatory Reaction1
2CompletedTreatmentGulf War Illness1
2CompletedTreatmentHIV test positive / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentHazardous Drinking / Smoking, Cigarette1
2CompletedTreatmentHeroin Dependence2
2CompletedTreatmentHeroin Dependence / Opioid-Related Disorders / Substance-Related Disorders1
2CompletedTreatmentKleptomania1
2CompletedTreatmentMajor Depressive Disorder (MDD) / Recurrences / Relapses / Unipolar Depression1
2CompletedTreatmentMalignant Gliomas1
2CompletedTreatmentMethamphetamine Dependence2
2CompletedTreatmentNicotine Dependence1
2CompletedTreatmentOpiate Dependence4
2CompletedTreatmentOpiate Dependence / Opioid Dependence1
2CompletedTreatmentOpioid Dependence1
2CompletedTreatmentOpioid-Related Disorders1
2CompletedTreatmentPain, Chronic1
2CompletedTreatmentPathological Gambling1
2CompletedTreatmentSmoking1
2CompletedTreatmentTrichotillomania1
2Enrolling by InvitationTreatmentPrescription Opiate/Medication Dependence1
2Not Yet RecruitingTreatmentChurg-Strauss Syndrome (CSS) / Eosinophilic Granulomatosis With Polyangiitis (EGPA) / Giant Cells Arteritis / Granulomatosis With Polyangiitis / Microscopic Polyangiitis / Polyarteritis Nodosa / Takayasu's Disease1
2RecruitingTreatmentAlcohol Use Disorder (AUD) / Nicotine Dependence1
2RecruitingTreatmentAlcohol Use Disorder (AUD) / Post Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentBinge Drinking / Human Immunodeficiency Virus (HIV)1
2RecruitingTreatmentDry Eye Syndrome (DES)1
2RecruitingTreatmentOsteoarthritis (OA) / Psoriatic Arthritis / Rheumatoid Arthritis1
2TerminatedTreatmentCancer, Breast1
2TerminatedTreatmentMelanoma / Prostate Cancer / Renal Cancers1
2TerminatedTreatmentObsessive Compulsive Disorder (OCD)1
2Unknown StatusTreatmentCocaine Abuse / Cocaine-Related Disorders1
2Unknown StatusTreatmentOpioid-Dependence Among Adolescents1
2WithdrawnTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Opiate Dependence1
2WithdrawnTreatmentOpioid-Related Disorders2
2WithdrawnTreatmentPyromania1
2, 3Active Not RecruitingTreatmentHeroin Dependence / Opioid-Related Disorders1
2, 3Active Not RecruitingTreatmentOpiate Dependence1
2, 3CompletedTreatmentAlcohol Dependence1
2, 3CompletedTreatmentDependence, Cocaine1
2, 3CompletedTreatmentHeroin Dependence / Opioid Dependence1
2, 3CompletedTreatmentOpiate Addiction1
2, 3CompletedTreatmentOpioid Dependence1
2, 3CompletedTreatmentReduction in Heavy Drinking in Patients With HIV1
2, 3Enrolling by InvitationTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m22
2, 3RecruitingTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m21
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Opiate Dependence1
2, 3RecruitingTreatmentOpioid-use Disorder1
2, 3RecruitingTreatmentSubstance, Addiction1
2, 3Unknown StatusTreatmentTobacco Use Disorders1
3Active Not RecruitingTreatmentOpioid Use Disorders1
3CompletedNot AvailableWithdrawal Symptoms1
3CompletedBasic ScienceAlcohol Dependence1
3CompletedTreatmentAlcohol Abuse / Alcohol Dependence / Alcohol Drinking / Alcohol-Related Disorders1
3CompletedTreatmentAlcohol Dependence11
3CompletedTreatmentAlcohol Dependence / Dependence, Cocaine2
3CompletedTreatmentAlcohol Dependence / Depression / Post Traumatic Stress Disorder (PTSD)1
3CompletedTreatmentAlcohol Use Disorder (AUD) / Opioid Use Disorders1
3CompletedTreatmentAmphetamine Dependence1
3CompletedTreatmentAnalgesia / Back Pain Lower Back / Pain, Chronic1
3CompletedTreatmentDisseminated Sclerosis1
3CompletedTreatmentGambling1
3CompletedTreatmentHeroin Dependence / Opiate Dependence1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentOpiate Dependence4
3CompletedTreatmentOpioid Dependence1
3CompletedTreatmentOpioid Use Disorders1
3CompletedTreatmentOsteoarthritis (OA) / Pain, Chronic1
3CompletedTreatmentPain NOS1
3CompletedTreatmentTobacco Use Disorders1
3RecruitingTreatmentAlcohol Dependence1
3RecruitingTreatmentBMI >30 kg/m21
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Substance Abuse1
3RecruitingTreatmentOpioid-use Disorder1
3TerminatedTreatmentAlcohol Dependence / Opiate Dependence1
3TerminatedTreatmentBMI >27 kg/m2 / BMI >30 kg/m21
3TerminatedTreatmentBorderline Personality Disorder (BPD)1
3Unknown StatusTreatmentAlcohol Abuse / Alcohol Dependence1
3Unknown StatusTreatmentMental Retardation / Self-Injurious Behavior1
4Active Not RecruitingTreatmentAlcohol Dependence1
4Active Not RecruitingTreatmentBMI >30 kg/m21
4Active Not RecruitingTreatmentHeroin Dependence / Opioid Dependence1
4Active Not RecruitingTreatmentSubstance, Addiction1
4CompletedBasic ScienceAlcohol Dependence / Attention Deficit Disorder With Hyperactivity (ADHD) / Attention Deficit Hyperactivity Disorder and Alcohol Dependence / Healthy Volunteers1
4CompletedBasic ScienceHeroin Dependence / Opioid-Related Disorders1
4CompletedBasic ScienceNeuroscience of Dreaming, Healthy1
4CompletedDiagnosticHealthy Volunteers1
4CompletedTreatmentAlcohol Abuse / Alcohol Dependence / Alcohol-Related Disorders / Psychiatric Disorder NOS / Schizophrenic Disorders1
4CompletedTreatmentAlcohol Consumption1
4CompletedTreatmentAlcohol Consumption / Alcohol Dependence / Alcohol-Induced Disorders / Alcoholic Intoxication1
4CompletedTreatmentAlcohol Dependence17
4CompletedTreatmentAlcohol Dependence / Alcohol Drinking1
4CompletedTreatmentAlcohol Dependence / Bipolar Disorder (BD)1
4CompletedTreatmentAlcohol Dependence / Bipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentAlcohol Dependence / Depression3
4CompletedTreatmentAlcohol Dependence / Eating Disorder1
4CompletedTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentAlcohol Dependence / Smoking2
4CompletedTreatmentAlcohol Use Disorder (AUD) / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Stimulant-Induced Euphoria1
4CompletedTreatmentCigarette-smoking / Obese / Schizophrenic Disorders1
4CompletedTreatmentImpulse Control Disorder / Parkinson's Disease (PD)1
4CompletedTreatmentOpioid Dependence1
4CompletedTreatmentOpioid Use Disorders1
4CompletedTreatmentSubstance-Related Disorders1
4Enrolling by InvitationOtherOpioid-Related Disorders1
4Enrolling by InvitationTreatmentAlcohol Dependence / Alcohol Use Disorder (AUD) / Heavy Drinking1
4RecruitingHealth Services ResearchAddictions / Hepatitis / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Opioid Dependence / Tuberculosis Infection1
4RecruitingTreatmentAlcohol Dependence / Alcohol Use Disorder (AUD)1
4RecruitingTreatmentBMI >30 kg/m21
4RecruitingTreatmentBMI >30 kg/m2 / Schizophrenic Disorders / Type 2 Diabetes Mellitus1
4RecruitingTreatmentDepression1
4RecruitingTreatmentFibromyalgia1
4RecruitingTreatmentHeroin Dependence / Opioid-Related Disorders1
4RecruitingTreatmentOpioid-use Disorder1
4TerminatedHealth Services ResearchAlcohol Dependence1
4TerminatedSupportive CareDisease, Chronic / Pain NOS1
4TerminatedTreatmentAlcohol Dependence1
4TerminatedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
4TerminatedTreatmentBMI >30 kg/m2 / Cardiovascular Disease (CVD)1
4Unknown StatusTreatmentAlcohol Dependence1
4WithdrawnTreatmentHeavy Alcoholic Consumption / Human Immunodeficiency Virus (HIV) Infections1
4WithdrawnTreatmentOpiate Addiction1
4WithdrawnTreatmentSelf Mutilation / Self-Injurious Behavior1
Not AvailableActive Not RecruitingTreatmentBipolar Disorder (BD) / Schizoaffective Disorders / Schizophrenic Disorders / Schizophreniform Disorder / Severe Major Depression With Psychotic Features1
Not AvailableCompletedNot AvailableAddictions1
Not AvailableCompletedNot AvailableFood Addiction1
Not AvailableCompletedNot AvailableHealthy Adults1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Methamphetamine Abuse1
Not AvailableCompletedNot AvailableObsessive Compulsive Disorder (OCD)1
Not AvailableCompletedBasic ScienceBioavailability1
Not AvailableCompletedBasic SciencePsychology, Social1
Not AvailableCompletedBasic ScienceSocial Acceptance1
Not AvailableCompletedPreventionBMI >27 kg/m2 / BMI >30 kg/m2 / Cancer, Breast1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Alcohol Dependence / Hazardous Drinking / Human Immunodeficiency Virus (HIV) / Problem Drinking1
Not AvailableCompletedTreatmentAlcohol Use Disorders (AUD) / Tuberculosis Infection1
Not AvailableCompletedTreatmentBMI >30 kg/m2 / Schizoaffective Disorders / Schizophrenic Disorders1
Not AvailableCompletedTreatmentBinge Eating Disorder (BED)1
Not AvailableCompletedTreatmentConcurrent Alcohol Dependence and Pathological Gambling1
Not AvailableCompletedTreatmentFibromyalgia / Persian Gulf Syndrome1
Not AvailableCompletedTreatmentHypoglycemia1
Not AvailableCompletedTreatmentOpiate Addiction1
Not AvailableCompletedTreatmentOpioid Dependence1
Not AvailableCompletedTreatmentSmoking1
Not AvailableCompletedTreatmentSocial Drinker1
Not AvailableRecruitingNot AvailableAlcohol Dependence / Cocaine Abuse / Dependence, Cocaine / Opiate Dependence / Substance Abuse1
Not AvailableSuspendedOtherFatigue Syndrome, Chronic1
Not AvailableUnknown StatusNot AvailableFibromyalgia1
Not AvailableUnknown StatusTreatmentAlcohol-dependence1
Not AvailableWithdrawnBasic ScienceFacial Pain / Temporomandibular Disorders1
Not AvailableWithdrawnTreatmentFibromyalgia1

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
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
Capsule, extended releaseOral
ImplantSubcutaneous
Tablet, film coatedOral50 mg/1
TabletOral50 mg
Kit380 mg/1
Kit380 mg/4mL
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)
US7919499No2009-10-152029-10-15Us
US6537586No1999-11-122019-11-12Us
US6331317No1999-11-122019-11-12Us
US6667061Yes2000-11-252020-11-25Us
US5792477Yes1997-11-022017-11-02Us
US6395304No1999-11-122019-11-12Us
US7799345No2000-05-252020-05-25Us
US5916598Yes1997-11-022017-11-02Us
US6379703Yes1999-06-302019-06-30Us
US6495164No2000-05-252020-05-25Us
US6403114Yes1997-11-022017-11-02Us
US6379704No2000-05-192020-05-19Us
US6596316Yes1999-06-302019-06-30Us
US6713090No1999-11-122019-11-12Us
US6194006Yes1999-06-302019-06-30Us
US6264987No2000-05-192020-05-19Us
US6495166No1999-11-122019-11-12Us
US6534092No2000-05-192020-05-19Us
US6939033No1999-11-122019-11-12Us
US8685443No2005-07-032025-07-03Us
US8158156No2007-06-192027-06-19Us
US7682633No2007-06-192027-06-19Us
US8623418No2009-11-072029-11-07Us
US8685444No2005-07-032025-07-03Us
US8846104No2007-06-192027-06-19Us
US7815934No2007-12-122027-12-12Us
US7682634No2007-06-192027-06-19Us
US8877247No2007-06-192027-06-19Us
US8722085No2007-11-082027-11-08Us
US8318788No2007-11-082027-11-08Us
US7462626No2004-07-202024-07-20Us
US8815889No2004-07-202024-07-20Us
US9107837No2007-06-042027-06-04Us
US9125868No2007-11-082027-11-08Us
US8916195No2010-02-022030-02-02Us
US9248123No2012-01-132032-01-13Us
US8088786No2009-02-032029-02-03Us
US7375111No2005-03-262025-03-26Us

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

Taxonomy

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
Phenanthrene / Isoquinolone / Tetralin / Coumaran / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Aralkylamine / Piperidine / Cyclic alcohol / Tertiary alcohol
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, cyclopropanes, morphinane-like compound (CHEBI:7465)

Targets

Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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 November 14, 2018 12:45