Nalmefene

Nalmefene
Clinical data
Trade names	Selincro, Revex, others
Other names	Nalmetrene; 6-Desoxy-6-methylenenaltrexone; CPH-101; JF-1; Lu AA36143; NIH-10365; ORF-11676
AHFS/Drugs.com	Monograph
MedlinePlus	a605043
License data	EU EMA: by INN; US DailyMed: Nalmefene; US FDA: Nalmefene;
Routes of; administration	By mouth, intranasal, intramuscular injection, intravenous injection, subcutaneous
Drug class	Opioid antagonist
ATC code	N07BB05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	40–50% (orally)
Protein binding	45%
Metabolism	Liver
Elimination half-life	10.8 ± 5.2 hours
Excretion	Kidney
Identifiers
	IUPAC name 17-Cyclopropylmethyl-4,5α-epoxy-6-methylenemorphinan-3,14-diol;
CAS Number	55096-26-9 ; as HCl: 58895-64-0;
PubChem CID	5284594;
IUPHAR/BPS	1628;
DrugBank	DB06230; as HCl: DBSALT001446;
ChemSpider	4447642 ; as HCl: 4534959;
UNII	TOV02TDP9I; as HCl: K7K69QC05X;
KEGG	D05111; as HCl: D02104;
ChEBI	CHEBI:7457;
ChEMBL	ChEMBL982 ; as HCl: ChEMBL1201152;
CompTox Dashboard (EPA)	DTXSID8023347 ;
ECHA InfoCard	100.164.948
Chemical and physical data
Formula	C21H25NO3
Molar mass	339.435 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC(C1=C2[C@@]34[C@H]5O1)=CC=C2C[C@@H](N(CC4)CC6CC6)[C@]3(O)CCC5=C;
	InChI 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 ; Key:WJBLNOPPDWQMCH-MBPVOVBZSA-N ;
	(verify)

Nalmefene is a medication that is used in the treatment of opioid overdose and alcohol dependence.^[2]^[3] Nalmefene belongs to the class of opioid antagonists and can be taken by mouth, administered by injection, or delivered through nasal administration.^[7]

In terms of its chemical structure and biological activity, nalmefene is similar to another opioid antagonist called naltrexone, as they are both derivatives of opiates. However, nalmefene offers certain advantages over naltrexone. These include a longer elimination half-life, which means it stays in the body for a longer duration, improved absorption when taken by mouth, and no observed liver toxicity that is dependent on the dosage.^[8]

Nalmefene is available as a generic medication.^[9]

^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.
^ ^a ^b Cite error: The named reference UKlabel was invoked but never defined (see the help page).
^ ^a ^b "Revex- nalmefene hydrochloride injection, solution". DailyMed. Archived from the original on 21 January 2022. Retrieved 11 February 2022.
^ "Opvee- nalmefene hydrochloride spray". DailyMed. 19 June 2023. Retrieved 25 June 2023.
^ "Selincro EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 11 February 2022. Retrieved 11 February 2022.
^ Kyhl LE, Li S, Faerch KU, Soegaard B, Larsen F, Areberg J (February 2016). "Population pharmacokinetics of nalmefene in healthy subjects and its relation to μ-opioid receptor occupancy". British Journal of Clinical Pharmacology. 81 (2). Wiley: 290–300. doi:10.1111/bcp.12805. PMC 4833148. PMID 26483076.
^ "FDA Approves Prescription Nasal Spray to Reverse Opioid Overdose". U.S. Food and Drug Administration (FDA) (Press release). 23 May 2023. Retrieved 1 June 2023.
^ "Nalmefene". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Library of Medicine. 24 March 2020. PMID 31643618. Bookshelf ID: NBK548295. Archived from the original on 13 November 2021. Retrieved 12 February 2022.
^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 11 February 2022. Archived from the original on 12 February 2022. Retrieved 11 February 2022.

[1] "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.

[UKlabel-2] Cite error: The named reference UKlabel was invoked but never defined (see the help page).

[Revex_FDA_label-3] "Revex- nalmefene hydrochloride injection, solution". DailyMed. Archived from the original on 21 January 2022. Retrieved 11 February 2022.

[Opvee_FDA_label-4] "Opvee- nalmefene hydrochloride spray". DailyMed. 19 June 2023. Retrieved 25 June 2023.

[Selincro_EPAR-5] "Selincro EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 11 February 2022. Retrieved 11 February 2022.

[Kyhl_Li_Faerch_Soegaard_2016_pp._290–300-6] Kyhl LE, Li S, Faerch KU, Soegaard B, Larsen F, Areberg J (February 2016). "Population pharmacokinetics of nalmefene in healthy subjects and its relation to μ-opioid receptor occupancy". British Journal of Clinical Pharmacology. 81 (2). Wiley: 290–300. doi:10.1111/bcp.12805. PMC 4833148. PMID 26483076.

[7] "FDA Approves Prescription Nasal Spray to Reverse Opioid Overdose". U.S. Food and Drug Administration (FDA) (Press release). 23 May 2023. Retrieved 1 June 2023.

[livertox-8] "Nalmefene". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Library of Medicine. 24 March 2020. PMID 31643618. Bookshelf ID: NBK548295. Archived from the original on 13 November 2021. Retrieved 12 February 2022.

[FDA_CGT-9] "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 11 February 2022. Archived from the original on 12 February 2022. Retrieved 11 February 2022.

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