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

General Information of Drug (ID: DR1124)
Drug Name
Naftopidil
Synonyms
Naftopidil (Flivas); Naftopidil (unspecified); Naftopidil [INN]; Naftopidilum [Latin]; naftopidil; (+-)-1-(4-(2-Methoxyphenyl)piperazinyl)-3-(1-naphthyloxy)propan-2-ol; Avishot; Flivas; KT-611; 1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol; 1-Pioerazineethanol, 4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-; 4-(2-Methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-1-pioerazineethanol; 57149-07-2; BM-15275; BRN 0629965; C24H28N2O3; CHEMBL142635; NCGC00015718-06
Indication Prostatic hyperplasia [ICD11: GA90] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 392.5 Topological Polar Surface Area 45.2
Heavy Atom Count 29 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4418
ChEBI ID
CHEBI:31891
CAS Number
57149-07-2
TTD Drug ID
D04DKH
Formula
C24H28N2O3
Canonical SMILES
COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O
InChI
1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3
InChIKey
HRRBJVNMSRJFHQ-UHFFFAOYSA-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
R-Naftopidil DM002703
6603939
Unclear 1 [4]
S-Naftopidil DM002704
11452157
Unclear 1 [4]
R-Naftopidil metabolite M1 DM002705
131490
Unclear 2 [2] , [5]
R-Naftopidil metabolite M2 DM002706
131580
Unclear 2 [2] , [5]
R-Naftopidil metabolite M3 DM002707
131491
Unclear 2 [2] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003388 Naftopidil R-Naftopidil Unclear Unclear [4]
MR003389 Naftopidil S-Naftopidil Unclear Unclear [4]
MR003382 R-Naftopidil R-Naftopidil metabolite M1 Unclear CYP2C8 ... [2], [5]
MR003383 R-Naftopidil R-Naftopidil metabolite M2 Unclear CYP2D6 ... [2], [5]
MR003384 R-Naftopidil R-Naftopidil metabolite M3 Unclear CYP2C19 ... [2], [5]
MR003385 S-Naftopidil R-Naftopidil metabolite M1 Unclear CYP2C8 ... [2], [5]
MR003386 S-Naftopidil R-Naftopidil metabolite M2 Unclear CYP2C8 ... [2], [5]
MR003387 S-Naftopidil R-Naftopidil metabolite M3 Unclear CYP2D6 ... [2], [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [3]
References
1 ClinicalTrials.gov (NCT01922375) Clinical Trial to Evaluate the Efficacy and Safety of Naftopidil in Male Patients With Lower Urinary Tract Symptoms Associated With Benign Prostatic Hyperplasia.
2 Identification of human cytochrome P450 isozymes involved in the metabolism of naftopidil enantiomers in vitro. J Pharm Pharmacol. 2014 Nov;66(11):1534-51.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 U. S. FDA Label -Naftopidil
5 Characterization of Ca(2+)-antagonistic effects of three metabolites of the new antihypertensive agent naftopidil, (naphthyl)hydroxy-naftopidil, (phenyl)hydroxy-naftopidil, and O-desmethyl-naftopidil J Cardiovasc Pharmacol. 1991 Dec;18(6):918-25. doi: 10.1097/00005344-199112000-00020.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.