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]
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Therapeutic Class

Anticraving Agents

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.