Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5402)
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 Opiate dependence [ICD11: 6C43] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 339.4 Topological Polar Surface Area 52.9
Heavy Atom Count 25 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5284594
ChEBI ID
CHEBI:7457
CAS Number
55096-26-9
TTD Drug ID
D05VIL
Formula
C21H25NO3
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Nalmefene 3-O-glucuronide DM018621 N. A. Conjugation - O-glucuronidation 1 [3]
Nalmefene 3-O-sulfate DM018622 N. A. Conjugation - Sulfation 1 [3]
Nornalmefene DM015581
9971176
Oxidation - Dealkylation 1 [4]
Nornalmefene 3-O-glucuronide DM018620 N. A. Conjugation - O-glucuronidation 2 [4]
Nornalmefene 3-O-sulfate DM018619 N. A. Conjugation - Sulfation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010771 Nalmefene Nornalmefene Oxidation - Dealkylation CYP3A4 ... [4]
MR010774 Nalmefene Nalmefene 3-O-glucuronide Conjugation - O-glucuronidation UGT2B7 ... [3]
MR010775 Nalmefene Nalmefene 3-O-sulfate Conjugation - Sulfation Unclear [3]
MR010772 Nornalmefene Nornalmefene 3-O-sulfate Conjugation - Sulfation Unclear [4]
MR010773 Nornalmefene Nornalmefene 3-O-glucuronide Conjugation - O-glucuronidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Ema.europa:Nalmefene
3 Isolation of a novel morphinan 3-O-diglucuronide metabolite from dog urine
4 LABEL:Nalmefene

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