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

General Information of Drug (ID: DR0478)
Drug Name
Dextropropoxyphene
Synonyms
Destropropossifene; Destropropossifene [DCIT]; Dextropropoxifeno; Dextropropoxifeno [INN-Spanish]; Dextropropoxyphen; Dextropropoxyphene; Dextropropoxyphene [INN:BAN]; Dextropropoxyphenum; Dextropropoxyphenum [INN-Latin]; Dextroproxifeno; Dextroproxifeno [Spanish]; Femadol; Propoxyphene, (+)-; Proxagesic; d-Propoxyphene; Algafan; Antalvic; Darvon; propoxyphene; (+)-1,2-Diphenyl-2-propionoxy-3-methyl-4-dimethylaminobutane; (D)-PROPOXYPHENE; 4-Dimethylamino-3-methyl-1,2-diphenyl-2-propoxybutane; 469-62-5; SK 65; UNII-S2F83W92TK
Indication Lung cancer [ICD11: 2C25] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 339.5 Topological Polar Surface Area 29.5
Heavy Atom Count 25 Rotatable Bond Count 9
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
10100
PubChem SID
9610 ; 7979056 ; 8157284 ; 15025964 ; 29228634 ; 46506690 ; 48416483 ; 49896450 ; 53790711 ; 56464340 ; 57325958 ; 74390898 ; 96024506 ; 104239521 ; 104322376 ; 134337347 ; 134975162 ; 136279476 ; 136350241 ; 137003058 ; 139157528 ; 162221259 ; 175267938 ; 176267062 ; 179116862 ; 198954437 ; 223365928 ; 226413489 ; 241078575 ; 250138664
ChEBI ID
ChEBI:51173
CAS Number
469-62-5
TTD Drug ID
D0D4PB
Formula
C22H29NO2
Canonical SMILES
CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C
InChI
1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1
InChIKey
XLMALTXPSGQGBX-GCJKJVERSA-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
Nordextropropoxyphene DM006593
18804
Oxidation - N-demethyiation 1 [3] , [4]
Unclear DM009999 N. A. Hydrolysis - Ester hydrolysis 1 [3]
Unclear DM009999 N. A. Oxidation - Aromatic hydroxylation 1 [3]
Dinordextropropoxyphene DM006594 N. A. Oxidation - N-demethyiation 2 [3]
Unclear DM009999 N. A. Conjugation - Conjugation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007109 Dextropropoxyphene Nordextropropoxyphene Oxidation - N-demethyiation CYP2D6 ... [3], [4]
MR007111 Dextropropoxyphene Unclear Oxidation - Aromatic hydroxylation Unclear [3]
MR007110 Nordextropropoxyphene Dinordextropropoxyphene Oxidation - N-demethyiation Unclear [3]
MR007112 Unclear Unclear Conjugation - Conjugation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 ClinicalTrials.gov (NCT00378937) Oxycodone or Standard Pain Therapy in Treating Patients With Cancer Pain.
2 Different effects of inhibitors on the O- and N-demethylation of codeine in human liver microsomes. Eur J Clin Pharmacol. 1997;52(1):41-7.
3 CYP3A4 mediates dextropropoxyphene N-demethylation to nordextropropoxyphene: human in vitro and in vivo studies and lack of CYP2D6 involvement. Xenobiotica. 2004 Oct;34(10):875-87.
4 The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: in vitro studies using human liver microsomes. Br J Clin Pharmacol. 1994 Sep;38(3):243-8.

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