Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H25NO3.ClH.2H2O |
Molecular Weight | 411.92 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.Cl.[H][C@@]12OC3=C4C(C[C@H]5N(CC6CC6)CC[C@@]14[C@@]5(O)CCC2=C)=CC=C3O
InChI
InChIKey=XOBQQQVDLSMXCE-JVRGSUDVSA-N
InChI=1S/C21H25NO3.ClH.2H2O/c1-12-6-7-21(24)16-10-14-4-5-15(23)18-17(14)20(21,19(12)25-18)8-9-22(16)11-13-2-3-13;;;/h4-5,13,16,19,23-24H,1-3,6-11H2;1H;2*1H2/t16-,19+,20+,21-;;;/m1.../s1
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 | C21H25NO3 |
Molecular Weight | 339.4281 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Nalmefene is the first medication approved for alcoholism
with the primary goal of reducing alcohol intake in an as
needed approach. Nalmefene
received a marketing authorization valid throughout the
European Union on February 25, 2013 and is under development
in Asia. Nalmefene is an opioid system modulator with a
distinct μ, δ, and κ receptor profile. In vitro studies have demonstrated
that Nalmefene is a selective opioid receptor ligand
with antagonist activity at the μ and δ receptors and partial
agonist activity at the κ receptor. In vivo studies have demonstrated
that nalmefene reduces alcohol consumption, possibly
by modulating cortico-mesolimbic functions. In the US, immediate-release injectable nalmefene was approved in 1995 as an antidote for opioid overdose. It was sold under the trade name Revex. The product was discontinued by its manufacturer around 2008. Currently Nalmefene is sold under the trade name Selincro. Selincro is indicated for the reduction of alcohol consumption in adult patients with alcohol dependence who have a high drinking-risk level, without physical withdrawal symptoms and who do not require immediate detoxification.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.44 nM [Ki] | |||
9.3 nM [Ki] | |||
0.12 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Selincro Approved UseSelincro is indicated for the reduction of alcohol consumption in adult patients with alcohol dependence who have a high drinking-risk level, without physical withdrawal symptoms and who do not require immediate detoxification. Launch Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
155 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
177 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
24.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
57.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
109 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1320 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1876 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
191 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
12 mg single, intravenous dose: 12 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
274 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
29.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
314 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
385 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
24 mg single, intravenous dose: 24 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
647 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
11.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
12 mg single, intravenous dose: 12 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
24 mg single, intravenous dose: 24 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
18 mg 1 times / day steady, oral Recommended Dose: 18 mg, 1 times / day Route: oral Route: steady Dose: 18 mg, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: alcohol dependence and Schizoaffective Disorder Age Group: 39 years Sex: M Population Size: 1 Sources: |
Disc. AE: Psychiatric decompensation... AEs leading to discontinuation/dose reduction: Psychiatric decompensation (1 patient) Sources: |
300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
healthy, adult n = 4 Health Status: healthy Age Group: adult Sex: M Population Size: 4 Sources: |
|
300 mg single, oral Highest studied dose |
healthy, adult n = 4 Health Status: healthy Age Group: adult Sex: M Population Size: 4 Sources: |
|
0.75 ug/kg single, intravenous Highest studied dose Dose: 0.75 ug/kg Route: intravenous Route: single Dose: 0.75 ug/kg Sources: |
unhealthy, adult n = 3 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 3 Sources: |
DLT: Anesthesia reversal... Dose limiting toxicities: Anesthesia reversal (2 patients) Sources: |
0.5 ug/kg single, intravenous MTD Dose: 0.5 ug/kg Route: intravenous Route: single Dose: 0.5 ug/kg Sources: |
unhealthy, adult n = 18 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 18 Sources: |
DLT: Anesthesia reversal... Dose limiting toxicities: Anesthesia reversal (3 patients) Sources: |
20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Disc. AE: Dizziness... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Sources: |
5 mg 2 times / day steady, oral Studied dose Dose: 5 mg, 2 times / day Route: oral Route: steady Dose: 5 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Disc. AE: Dizziness, Rash... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Sources: Rash (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Psychiatric decompensation | 1 patient Disc. AE |
18 mg 1 times / day steady, oral Recommended Dose: 18 mg, 1 times / day Route: oral Route: steady Dose: 18 mg, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: alcohol dependence and Schizoaffective Disorder Age Group: 39 years Sex: M Population Size: 1 Sources: |
Anesthesia reversal | 2 patients DLT |
0.75 ug/kg single, intravenous Highest studied dose Dose: 0.75 ug/kg Route: intravenous Route: single Dose: 0.75 ug/kg Sources: |
unhealthy, adult n = 3 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 3 Sources: |
Anesthesia reversal | 3 patients DLT |
0.5 ug/kg single, intravenous MTD Dose: 0.5 ug/kg Route: intravenous Route: single Dose: 0.5 ug/kg Sources: |
unhealthy, adult n = 18 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 18 Sources: |
Dizziness | 1 patient Disc. AE |
20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Dizziness | 1 patient Disc. AE |
5 mg 2 times / day steady, oral Studied dose Dose: 5 mg, 2 times / day Route: oral Route: steady Dose: 5 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Rash | 1 patient Disc. AE |
5 mg 2 times / day steady, oral Studied dose Dose: 5 mg, 2 times / day Route: oral Route: steady Dose: 5 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Nalmefene: intravenous safety and kinetics of a new opioid antagonist. | 1986 Jan |
|
A double-blind, placebo-controlled pilot study to evaluate the efficacy and safety of oral nalmefene HCl for alcohol dependence. | 1994 Oct |
|
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. | 1998 Mar |
|
Dynorphin A1-13 causes elevation of serum levels of prolactin through an opioid receptor mechanism in humans: gender differences and implications for modulation of dopaminergic tone in the treatment of addictions. | 1999 Jan |
|
Pharmacologic approaches to the management of alcoholism. | 2001 |
|
Use of acamprosate and opioid antagonists in the treatment of alcohol dependence: a European perspective. | 2003 |
|
[Drug therapy of alcohol dependence--a critical review]. | 2003 |
|
A multi-site dose ranging study of nalmefene in the treatment of alcohol dependence. | 2004 Aug |
|
Synergistic effects of cannabinoid inverse agonist AM251 and opioid antagonist nalmefene on food intake in mice. | 2004 Mar 5 |
|
Opioid antagonists for alcohol dependence. | 2005 Jan 25 |
|
Unexpected placebo response in premenstrual dysphoric disorder: implication of endogenous opioids. | 2005 Oct |
|
Acamprosate: a new tool in the battle against alcohol dependence. | 2006 Dec |
|
Pharmacologic treatments for opioid dependence: detoxification and maintenance options. | 2007 |
|
Plasma met-enkephalin, beta-endorphin and leu-enkephalin levels in human hepatic encephalopathy. | 2007 Mar-Apr |
|
Emerging pharmacologic options for treating postoperative ileus. | 2007 Oct 15 |
|
Opioid-dependent anticipatory negative contrast and binge-like eating in rats with limited access to highly preferred food. | 2008 Feb |
|
Agenda for specialty section in addiction medicine. | 2008 Oct |
|
The effects of herkinorin, the first mu-selective ligand from a salvinorin A-derived scaffold, in a neuroendocrine biomarker assay in nonhuman primates. | 2008 Oct |
|
Primary biliary cirrhosis. | 2009 Sep |
|
The Effects of Naltrexone Among Alcohol Non-Abstainers: Results from the COMBINE Study. | 2010 |
|
In vivo characterization of the opioid antagonist nalmefene in mice. | 2010 Apr 10 |
|
Human exposures to immobilising agents: results of an online survey. | 2010 Aug 28 |
|
Emerging drugs to treat alcoholism. | 2010 Dec |
|
Opioid antagonists under heavy sedation or anaesthesia for opioid withdrawal. | 2010 Jan 20 |
|
[Clinical observation of the effect of nalmefene in treatment of septic shock]. | 2010 Jun |
|
[Serum NT-proBNP levels in neonates with severe asphyxia and the effects of nalmefene on the NT-proBNP levels]. | 2010 Nov |
|
Nalmefene for treatment of alcohol dependence. | 2010 Nov |
|
Nalmefene in the treatment of pathological gambling: multicentre, double-blind, placebo-controlled study. | 2010 Oct |
|
Brain imaging studies in pathological gambling. | 2010 Oct |
|
Tailoring therapeutic strategies for treating posttraumatic stress disorder symptom clusters. | 2010 Sep 7 |
|
Long-term efficacy, tolerability and safety of nalmefene as-needed in patients with alcohol dependence: A 1-year, randomised controlled study. | 2014 Aug |
|
Treatment of Gambling Disorders. | 2014 Jun 1 |
Patents
Sample Use Guides
How much to take
- The recommended dose is one tablet on days when you think there is a risk you will drink alcohol
- The maximum dose is one tablet per day.
How and when to take
- You should take the tablet 1-2 hours before you start drinking alcohol.
- Swallow the tablet whole, do not crush or divide the tablet.
- You can take Selincro (Nalmefene) with or without food.
Each film-coated tablet contains 18.06 mg nalmefene (as hydrochloride dihydrate).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2991678
Nalmefene antagonized the bindings of [3H]-dihydromorphine, [3H]-ethylketocyclazocine and [3H]-D-ala-D-leu enkephalin with IC50's in the low nanomolar range in rat brain membranes.. At the central mu receptor, nalmefene bound with an IC50 of 1.0 nM
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 06:19:39 GMT 2023
by
admin
on
Sat Dec 16 06:19:39 GMT 2023
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Record UNII |
52Z0G7QVJX
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
SELINCRO (AUTHORIZED: ALCOHOL-RELATED DISORDERS)
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DBSALT002636
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SUB130094
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |