Details of the Drug

General Information of Drug (ID: DM4YWCZ)

Drug Name
Nalmefene
Synonyms
Alcofene; Arthene; Cervene; Cessal; Incystene; Nalmefeno; Nalmefenum; Nalmetrene; Nalmetreno; Nalmetrenum; Revex; Soberal; JF 1; ORF 11676; JF-1; NIH-10365; Nalmefeno [INN-Spanish]; Nalmefenum [INN-Latin]; Nalmetreno [INN-Spanish]; Nalmetrenum [INN-Latin]; ORF-11676; Revex (TN); Nalmefene (USAN/INN); Nalmefene [USAN:BAN:INN]; (5alpha)-17-(Cyclopropylmethyl)-4,5-epoxy-6-methylenemorphinan-3,14-diol; (5alpha)-17-(Cyclopropylmethyl)-4,5-epoxy-6-methylenemorphinon-3,14-diol; (5alpha)-17-(cyclopropylmethyl)-6-methylidene-4,5-epoxymorphinan-3,14-diol; 17-(Cyclopropylmethyl)-4,5alpha-epoxy-6-methylenemorphinan-3,14-diol; 6-Desoxy-6-methylenenaltrexone; 9a-(Cyclopropylmethyl)-4,5alpha-epoxy-6-methylen-3,14-morphinandiol
Indication
Disease Entry ICD 11 Status REF
Opioid dependence 6C43.2Z Approved [1]
Therapeutic Class
Anticraving Agents
Affected Organisms
Humans and other mammals
ATC Code
N07BB05: Nalmefene
N07BB: Drugs used in alcohol dependence
N07B: DRUGS USED IN ADDICTIVE DISORDERS
N07: OTHER NERVOUS SYSTEM DRUGS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 339.4
Logarithm of the Partition Coefficient (xlogp) 2.7
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 131 mcgh/L [2]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 16.5 mcg/L [2]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.5 h [2]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Clearance
The renal clearance of drug is 0.08 +/- 0.04 L/h/kg [2]
Elimination
54% of the total dose is excreted in the urine as nalmefene 3-O-glucuronide [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 12.5 hours [2]
Metabolism
The drug is metabolized via the hepatic [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 2.79757 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.65% [5]
Vd
The volume of distribution (Vd) of drug is 3200 L [2]
Water Solubility
The ability of drug to dissolve in water is measured as 124 mg/mL [3]
Chemical Identifiers
Formula
C21H25NO3
IUPAC Name
(4R,4aS,7aS,12bS)-3-(cyclopropylmethyl)-7-methylidene-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
Canonical SMILES
C=C1CC[C@]2([C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3CC6CC6)O
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
InChIKey
WJBLNOPPDWQMCH-MBPVOVBZSA-N
Cross-matching ID
PubChem CID
5284594
ChEBI ID
CHEBI:7457
CAS Number
55096-26-9
UNII
TOV02TDP9I
DrugBank ID
DB06230
TTD ID
D05VIL

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Opioid receptor (OPR) TTN4QDT NOUNIPROTAC Antagonist [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 European Medicines Agency (EMA) Summary of product characteristics: Selincro
3 BDDCS applied to over 900 drugs
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Unconditioned behavioral effects of the powerful kappa-opioid hallucinogen salvinorin A in nonhuman primates: fast onset and entry into cerebrospin... J Pharmacol Exp Ther. 2009 Feb;328(2):588-97.