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

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
Structure of NALMEFENE

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

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.44 nM [Ki]
9.3 nM [Ki]
0.12 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Selincro

Cmax

ValueDoseCo-administeredAnalytePopulation
155 ng/mL
200 mg single, oral
NALMEFENE plasma
Homo sapiens
177 ng/mL
300 mg single, oral
NALMEFENE plasma
Homo sapiens
24.3 ng/mL
50 mg single, oral
NALMEFENE plasma
Homo sapiens
57.9 ng/mL
100 mg single, oral
NALMEFENE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
109 ng × h/mL
6 mg single, intravenous
NALMEFENE plasma
Homo sapiens
1320 ng × h/mL
200 mg single, oral
NALMEFENE plasma
Homo sapiens
16.6 ng × h/mL
1 mg single, intravenous
NALMEFENE plasma
Homo sapiens
16.9 ng × h/mL
2 mg single, intravenous
NALMEFENE plasma
Homo sapiens
1876 ng × h/mL
300 mg single, oral
NALMEFENE plasma
Homo sapiens
191 ng × h/mL
12 mg single, intravenous
NALMEFENE plasma
Homo sapiens
274 ng × h/mL
50 mg single, oral
NALMEFENE plasma
Homo sapiens
29.4 ng × h/mL
2 mg single, intravenous
NALMEFENE plasma
Homo sapiens
314 ng × h/mL
20 mg 2 times / day steady-state, oral
NALMEFENE plasma
Homo sapiens
385 ng × h/mL
24 mg single, intravenous
NALMEFENE plasma
Homo sapiens
647 ng × h/mL
100 mg single, oral
NALMEFENE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.2 h
6 mg single, intravenous
NALMEFENE plasma
Homo sapiens
9.8 h
200 mg single, oral
NALMEFENE plasma
Homo sapiens
10.8 h
1 mg single, intravenous
NALMEFENE plasma
Homo sapiens
11.7 h
300 mg single, oral
NALMEFENE plasma
Homo sapiens
8.6 h
12 mg single, intravenous
NALMEFENE plasma
Homo sapiens
10.3 h
50 mg single, oral
NALMEFENE plasma
Homo sapiens
9.4 h
2 mg single, intravenous
NALMEFENE plasma
Homo sapiens
9.1 h
20 mg 2 times / day steady-state, oral
NALMEFENE plasma
Homo sapiens
8.9 h
24 mg single, intravenous
NALMEFENE plasma
Homo sapiens
11.4 h
100 mg single, oral
NALMEFENE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
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