Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H25NO3 |
Molecular Weight | 339.4281 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC3=C4C(C[C@H]5N(CC6CC6)CC[C@@]14[C@@]5(O)CCC2=C)=CC=C3O
InChI
InChIKey=WJBLNOPPDWQMCH-MBPVOVBZSA-N
InChI=1S/C21H25NO3/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/t16-,19+,20+,21-/m1/s1
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 Date1.36175039E12 |
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 panic attack precipitated by opiate blockade--a case study. | 1987 Oct |
|
Acute effects of nalmefene on LH, prolactin, and testosterone in male rhesus monkeys. | 2000 Jun |
|
Pharmacologic approaches to the management of alcoholism. | 2001 |
|
Pharmacological control of opioid-induced pruritus: a quantitative systematic review of randomized trials. | 2001 Jun |
|
Opioid antagonists for alcohol dependence. | 2002 |
|
Preclinical models to evaluate potential pharmacotherapeutic agents in treating alcoholism and studying the neuropharmacological bases of ethanol-seeking behaviors in rats. | 2002 Aug |
|
Potentiation of the excitatory action of NMDA in ventrolateral periaqueductal gray by the mu-opioid receptor agonist, DAMGO. | 2002 May 10 |
|
A clinical laboratory paradigm for evaluating medication effects on alcohol consumption: naltrexone and nalmefene. | 2003 Apr |
|
[Pathogenesis and treatment of pruritus in patients with cholestasis]. | 2003 Mar |
|
Characterization of scratching responses in rats following centrally administered morphine or bombesin. | 2003 Nov |
|
Central opioid receptors differentially regulate the nalmefene-induced suppression of ethanol- and saccharin-reinforced behaviors in alcohol-preferring (P) rats. | 2004 Feb |
|
Chronic administration of nalmefene leads to increased food intake and body weight gain in mice. | 2004 Jul 8 |
|
Synergistic effects of cannabinoid inverse agonist AM251 and opioid antagonist nalmefene on food intake in mice. | 2004 Mar 5 |
|
Pharmacotherapy for erectile dysfunction. | 2004 Sep |
|
Determination of nalmefene by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. | 2005 Apr |
|
The permeation of nalmefene hydrochloride across different regions of ovine nasal mucosa. | 2006 Dec |
|
Epidemiologic and clinical updates on impulse control disorders: a critical review. | 2006 Dec |
|
Pathological gambling: focusing on the addiction, not the activity. | 2006 Feb |
|
Pharmacologic treatments for opioid dependence: detoxification and maintenance options. | 2007 |
|
Targeted nalmefene with simple medical management in the treatment of heavy drinkers: a randomized double-blind placebo-controlled multicenter study. | 2007 Jul |
|
Application of a sensitive liquid chromatographic/tandem mass spectrometric method to pharmacokinetic study of nalmefene in humans. | 2007 Jun 1 |
|
Methylnaltrexone in the treatment of opioid-induced constipation. | 2008 |
|
Effects of opioid receptor gene variation on targeted nalmefene treatment in heavy drinkers. | 2008 Jul |
|
Cholestatic hepatitis as a possible new side-effect of oxycodone: a case report. | 2008 May 1 |
|
Agenda for specialty section in addiction medicine. | 2008 Oct |
|
Unconditioned behavioral effects of the powerful kappa-opioid hallucinogen salvinorin A in nonhuman primates: fast onset and entry into cerebrospinal fluid. | 2009 Feb |
|
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 |
|
Opioid antagonists under heavy sedation or anaesthesia for opioid withdrawal. | 2010 Jan 20 |
|
Nalmefene for treatment of alcohol dependence. | 2010 Nov |
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
Thu Jul 06 23:05:07 UTC 2023
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on
Thu Jul 06 23:05:07 UTC 2023
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Record UNII |
TOV02TDP9I
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C681
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NDF-RT |
N0000000154
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WHO-VATC |
QN07BB05
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WHO-ATC |
N07BB05
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N0000175691
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NBK548295
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SUB09139MIG
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M7715
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> INHIBITOR |
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MINOR
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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