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

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23NO4.ClH
Molecular Weight 377.862
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALTREXONE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=RHBRMCOKKKZVRY-ITLPAZOVSA-N
InChI=1S/C20H23NO4.ClH/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/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 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
Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors.
1994 Feb
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
Therapeutic options and challenges for substances of abuse.
2007
Naltrexone for the treatment of alcoholism: clinical findings, mechanisms of action, and pharmacogenetics.
2010 Mar
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
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on Fri Dec 15 15:15:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:35 GMT 2023
Record UNII
Z6375YW9SF
Record Status Validated (UNII)
Record Version
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Name Type Language
NALTREXONE HYDROCHLORIDE
EP   GREEN BOOK   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
NALTREXONE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
NALTREXONE HYDROCHLORIDE COMPONENT OF CONTRAVE
Brand Name English
EN-1639A
Code English
NALTREXONE HYDROCHLORIDE COMPONENT OF EMBEDA
Common Name English
NALTREXONE HYDROCHLORIDE COMPONENT OF TROXYCA
Brand Name English
Naltrexone hydrochloride [WHO-DD]
Common Name English
EMBEDA COMPONENT NALTREXONE HYDROCHLORIDE
Common Name English
MORPHINAN-6-ONE, 17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-3,14-DIHYDROXY-, HYDROCHLORIDE, (5.ALPHA.)-
Systematic Name English
CONTRAVE COMPONENT NALTREXONE HYDROCHLORIDE
Brand Name English
NALTREXONE HYDROCHLORIDE [MI]
Common Name English
REVIA
Brand Name English
NALTREXONE HYDROCHLORIDE [GREEN BOOK]
Common Name English
NALTREXONE HYDROCHLORIDE [VANDF]
Common Name English
NALTREXONE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
TROXYCA COMPONENT NALTREXONE HYDROCHLORIDE
Brand Name English
17-Cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride
Common Name English
TREXAN
Brand Name English
EN-1639A (AS HYDROCHLORIDE)
Code English
NALTREXONE HYDROCHLORIDE [MART.]
Common Name English
NALTREXONE HCL
Common Name English
NALTREXONE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 6085
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
EMA ASSESSMENT REPORTS MYSIMBA (AUTHORIZED: OVERWEIGHT)
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
EU-Orphan Drug EU/3/14/1260
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
NCI_THESAURUS C681
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
CFR 21 CFR 522.1465
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
EMA ASSESSMENT REPORTS MYSIMBA (AUTHORIZED: OBESITY)
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
Code System Code Type Description
MERCK INDEX
m7718
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY Merck Index
SMS_ID
100000089938
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
FDA UNII
Z6375YW9SF
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
RXCUI
105069
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY RxNorm
CAS
16676-29-2
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
PUBCHEM
5388998
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
EVMPD
SUB14629MIG
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
DRUG BANK
DBSALT000670
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL19019
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
DAILYMED
Z6375YW9SF
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
240-723-0
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
NCI_THESAURUS
C679
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID50937236
Created by admin on Fri Dec 15 15:15:35 GMT 2023 , Edited by admin on Fri Dec 15 15:15:35 GMT 2023
PRIMARY
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