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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23NO4.ClH.2H2O
Molecular Weight 413.892
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALTREXONE HYDROCHLORIDE DIHYDRATE

SMILES

O.O.Cl.[H][C@@]12OC3=C4C(C[C@H]5N(CC6CC6)CC[C@@]14[C@@]5(O)CCC2=O)=CC=C3O

InChI

InChIKey=RMRRPHDKLROLJJ-VNANXUGNSA-N
InChI=1S/C20H23NO4.ClH.2H2O/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;1H;2*1H2/t15-,18+,19+,20-;;;/m1.../s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H23NO4
Molecular Weight 341.4009
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

2006
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

2006
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
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
Vivitrex, an injectable, extended-release formulation of naltrexone, provides pharmacokinetic and pharmacodynamic evidence of efficacy for 1 month in rats.
2003 Nov
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Pharmacoprophylaxis of alcohol dependence: Review and update Part II: Efficacy.
2007 Jan
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:11:30 GMT 2023
Edited
by admin
on Sat Dec 16 09:11:30 GMT 2023
Record UNII
5P80UKS30B
Record Status Validated (UNII)
Record Version
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Name Type Language
NALTREXONE HYDROCHLORIDE DIHYDRATE
Common Name English
MORPHINAN-6-ONE, 17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-3,14-DIHYDROXY-, HYDROCHLORIDE, HYDRATE (1:1:2), (5.ALPHA.)-
Systematic Name English
Code System Code Type Description
EVMPD
SUB16164MIG
Created by admin on Sat Dec 16 09:11:30 GMT 2023 , Edited by admin on Sat Dec 16 09:11:30 GMT 2023
PRIMARY
PUBCHEM
16219735
Created by admin on Sat Dec 16 09:11:30 GMT 2023 , Edited by admin on Sat Dec 16 09:11:30 GMT 2023
PRIMARY
CAS
850808-02-5
Created by admin on Sat Dec 16 09:11:30 GMT 2023 , Edited by admin on Sat Dec 16 09:11:30 GMT 2023
PRIMARY
SMS_ID
100000079953
Created by admin on Sat Dec 16 09:11:30 GMT 2023 , Edited by admin on Sat Dec 16 09:11:30 GMT 2023
PRIMARY
FDA UNII
5P80UKS30B
Created by admin on Sat Dec 16 09:11:30 GMT 2023 , Edited by admin on Sat Dec 16 09:11:30 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY