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
SMILES
Cl.OC1=CC=C2C[C@H]3N(CC4CC4)CC[C@@]56[C@@H](OC1=C25)C(=O)CC[C@@]36O
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
| 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 |
| 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 |
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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095181 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | VIVITROL Approved UseNaltrexone 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 Date2006 |
|||
| Preventing | VIVITROL Approved UseNaltrexone 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 Date2006 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
579 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637968/ |
2.4 mg single, oral dose: 2.4 mg route of administration: Oral experiment type: SINGLE co-administered: MORPHINE SULFATE |
NALTREXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
12.27 ng/mL |
45.2 g single, oral dose: 45.2 g route of administration: Oral experiment type: SINGLE co-administered: |
NALTREXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16239359 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1811 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637968/ |
2.4 mg single, oral dose: 2.4 mg route of administration: Oral experiment type: SINGLE co-administered: MORPHINE SULFATE |
NALTREXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
43.31 ng × h/mL |
45.2 g single, oral dose: 45.2 g route of administration: Oral experiment type: SINGLE co-administered: |
NALTREXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16239359 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6469932/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALTREXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.99 h |
45.2 g single, oral dose: 45.2 g route of administration: Oral experiment type: SINGLE co-administered: |
NALTREXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN 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 |
|
5.6 day EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16239359 |
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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
79% |
45.2 g unknown, oral dose: 45.2 g route of administration: Oral experiment type: UNKNOWN co-administered: |
NALTREXONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Critical appraisal of once-weekly formulation of exenatide in the control of type 2 diabetes mellitus. | 2010-05-17 |
|
| Naltrexone for the treatment of alcoholism: clinical findings, mechanisms of action, and pharmacogenetics. | 2010-03 |
|
| The effects of maternally administered methadone, buprenorphine and naltrexone on offspring: review of human and animal data. | 2008-06 |
|
| 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". | 2008-01 |
|
| Pharmacoprophylaxis of alcohol dependence: Review and update Part II: Efficacy. | 2007-01 |
|
| Therapeutic options and challenges for substances of abuse. | 2007 |
|
| A synopsis of the pharmacological rationale, properties and therapeutic effects of depot preparations of naltrexone for treating alcohol dependence. | 2006-06 |
|
| Vivitrex (Alkermes/Cephalon). | 2006-01 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| The preclinical development of Medisorb Naltrexone, a once a month long acting injection, for the treatment of alcohol dependence. | 2005-01-01 |
|
| A pilot evaluation of the safety and tolerability of repeat dose administration of long-acting injectable naltrexone (Vivitrex) in patients with alcohol dependence. | 2004-09 |
|
| Vivitrex, an injectable, extended-release formulation of naltrexone, provides pharmacokinetic and pharmacodynamic evidence of efficacy for 1 month in rats. | 2003-11 |
|
| Naltrexone and relapse prevention treatment for cocaine-dependent patients. | 2001-04-24 |
|
| Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. | 1998-03 |
|
| kappa-Opioid receptor in humans: cDNA and genomic cloning, chromosomal assignment, functional expression, pharmacology, and expression pattern in the central nervous system. | 1995-07-18 |
|
| Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors. | 1994-02 |
|
| Cloning and functional comparison of kappa and delta opioid receptors from mouse brain. | 1993-07-15 |
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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| Record UNII |
Z6375YW9SF
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Validated (UNII)
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
6085
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EMA ASSESSMENT REPORTS |
MYSIMBA (AUTHORIZED: OVERWEIGHT)
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EU-Orphan Drug |
EU/3/14/1260
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NCI_THESAURUS |
C681
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CFR |
21 CFR 522.1465
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EMA ASSESSMENT REPORTS |
MYSIMBA (AUTHORIZED: OBESITY)
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m7718
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100000089938
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Z6375YW9SF
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105069
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16676-29-2
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C679
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DTXSID50937236
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