U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23NO4
Molecular Weight 341.4017
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALTREXONE

SMILES

C1CC1CN2CC[C@@]34c5c6ccc(c5O[C@@]4([H])C(=O)CC[C@]3([C@@]2([H])C6)O)O

InChI

InChIKey=DQCKKXVULJGBQN-XFWGSAIBSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including

Naltrexone is marketed as its hydrochloride salt, naltrexone hydrochloride, under the trade names Revia and Depade. A once-monthly extended-release injectable formulation is marketed under the trade name Vivitrol. VIVITROL is indicated for the treatment of alcohol dependence in patients who are able to abstain from alcohol in an outpatient setting prior to initiation of treatment with VIVITROL. VIVITROL is indicated for the prevention of relapse to opioid dependence, following opioid detoxification. 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 affinity 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. Low dose naltrexone is an “off label” use of naltrexone. Normal naltrexone usage to break addictions is 50mg – 100mg. Usage of low dose naltrexone ranges in the area of 3 mg – 4.5 mg dosing and is prescribed in an oral pill form and is quite inexpensive. For people with multiple sclerosis, the dosage of LDN ranges from 1.5 to 4.5 ml per day.

Originator

Curator's Comment:: Naltrexone first synthesized by Endo Laboratories in Long Island, NY in 1962

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIVITROL

Approved Use

Naltrexone hydrochloride tablets are indicated: In the treatment of alcohol dependence and for the blockade of the effects of exogenously administered opioids. Naltrexone hydrochloride tablets have not been shown to provide any therapeutic benefit except as part of an appropriate plan of management for the addictions.

Launch Date

1.14488639E12
Preventing
VIVITROL

Approved Use

Naltrexone hydrochloride tablets are indicated: In the treatment of alcohol dependence and for the blockade of the effects of exogenously administered opioids. Naltrexone hydrochloride tablets have not been shown to provide any therapeutic benefit except as part of an appropriate plan of management for the addictions.

Launch Date

1.14488639E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9.7 ng/mL
190 mg single, intramuscular
dose: 190 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.4 ng × h/mL
190 mg single, intramuscular
dose: 190 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.6 day
190 mg single, intramuscular
dose: 190 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
180 h
380 mg single, intramuscular
dose: 380 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALTREXONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
79%
380 mg single, intramuscular
dose: 380 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALTREXONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.
1993 Jul 15
Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors.
1994 Feb
kappa-Opioid receptor in humans: cDNA and genomic cloning, chromosomal assignment, functional expression, pharmacology, and expression pattern in the central nervous system.
1995 Jul 18
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
Naltrexone and relapse prevention treatment for cocaine-dependent patients.
2001 Mar-Apr
Vivitrex, an injectable, extended-release formulation of naltrexone, provides pharmacokinetic and pharmacodynamic evidence of efficacy for 1 month in rats.
2003 Nov
A pilot evaluation of the safety and tolerability of repeat dose administration of long-acting injectable naltrexone (Vivitrex) in patients with alcohol dependence.
2004 Sep
The preclinical development of Medisorb Naltrexone, a once a month long acting injection, for the treatment of alcohol dependence.
2005 Jan 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Vivitrex (Alkermes/Cephalon).
2006 Jan
A synopsis of the pharmacological rationale, properties and therapeutic effects of depot preparations of naltrexone for treating alcohol dependence.
2006 Jun
Therapeutic options and challenges for substances of abuse.
2007
Pharmacoprophylaxis of alcohol dependence: Review and update Part II: Efficacy.
2007 Jan
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".
2008 Jan
The effects of maternally administered methadone, buprenorphine and naltrexone on offspring: review of human and animal data.
2008 Jun
Naltrexone for the treatment of alcoholism: clinical findings, mechanisms of action, and pharmacogenetics.
2010 Mar
Critical appraisal of once-weekly formulation of exenatide in the control of type 2 diabetes mellitus.
2010 May 17
Patents

Sample Use Guides

The recommended dose of VIVITROL (naltrexone for extended-release injectable suspension) is 380 mg delivered intramuscularly every 4 weeks or once a month.
Route of Administration: Intramuscular
In Vitro Use Guide
Curator's Comment:: In vitro study suggest that treatment of alcohol or opiate dependent HIV-1-infected patients with naltrexone is unlikely to interfere with the activity of antiretroviral drugs. Also, based upon naltrexone's safety profile and its synergistic activity in vitro, these findings suggest clinical trials should be considered of naltrexone as an adjunctive therapy of HIV-1 infection.
at a concentration of 10(-12)-10(-10) M naltrexone increased the antiviral activity of zidovudine (AZT) and indinavir 2-3-fold
Name Type Language
NALTREXONE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
EN-1639A FREE BASE
Code English
NALTREXONE [VANDF]
Common Name English
NALTREXONE [USP-RS]
Common Name English
NALTREXONE [INN]
Common Name English
17-(CYCLOPROPYLMETHYL)-4,5.ALPHA.-EPOXY-3,14-DIHYDROXYMORPHINAN-6-ONE
Systematic Name English
NALTREXONE [HSDB]
Common Name English
NALTREXONE [ORANGE BOOK]
Common Name English
NALTREXONE COMPONENT OF CONTRAVE
Brand Name English
MORPHINAN-6-ONE, 17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-3,14-DIHYDROXY-, (5.ALPHA.)-
Systematic Name English
NALTREXONE [MI]
Common Name English
NSC-758439
Code English
NALTREXONE [USAN]
Common Name English
NALTREXONE [WHO-DD]
Common Name English
VIVITROL
Brand Name English
NALTREXONE [MART.]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug Naltrexone
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
WHO-ATC N02AA56
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
WHO-ATC A08AA62
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
LIVERTOX 666
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
FDA ORPHAN DRUG 425614
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
NDF-RT N0000175691
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
FDA ORPHAN DRUG 465614
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
FDA ORPHAN DRUG 422914
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
FDA ORPHAN DRUG 296909
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
WHO-ATC N07BB04
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
NCI_THESAURUS C681
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
WHO-VATC QN07BB04
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
NDF-RT N0000000154
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
FDA ORPHAN DRUG 460314
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
WHO-ATC N02AA56
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
Code System Code Type Description
PUBCHEM
5360515
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
EPA CompTox
16590-41-3
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
EVMPD
SUB09143MIG
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
HSDB
6750
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
DRUG CENTRAL
1765
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
MERCK INDEX
M7718
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
240-649-9
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
CAS
16590-41-3
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
LACTMED
Naltrexone
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
NCI_THESAURUS
C62055
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
WIKIPEDIA
NALTREXONE
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
FDA UNII
5S6W795CQM
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
MESH
D009271
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
INN
3368
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
DRUG BANK
DB00704
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL19019
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
IUPHAR
1639
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY
USP_CATALOG
1453504
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY USP-RS
RXCUI
7243
Created by admin on Fri Jun 25 22:02:22 UTC 2021 , Edited by admin on Fri Jun 25 22:02:22 UTC 2021
PRIMARY RxNorm