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

General Information of Drug (ID: DR0708)
Drug Name
Flunarizine
Synonyms
Flunarizin; Flunarizina; Flunarizina [INN-Spanish]; Flunarizine [INN:BAN]; Flunarizinum; Flunarizinum [INN-Latin]; R7PLA2DM0J; Sibelium; flunarizine; (E)-1-(Bis(4-fluorophenyl)methyl)-4-(3-phenyl-2-propenyl)piperazine; (E)-1-[Bis-(p-fluorophenyl)methyl]-4-cinnamylpiperazine; 1-(Bis(4-fluorophenyl)methyl)-4-cinnamylpiperazine; 1-[bis(4-fluorophenyl)methyl]-4-(3-phenylprop-2-en-1-yl)piperazine; 52468-60-7; CHEMBL30008; EINECS 257-937-5; Piperazine, 1-(bis(4-fluorophenyl)methyl)-4-(3-phenyl-2-propenyl)-, (E)-; UNII-R7PLA2DM0J
Indication Schizophrenia [ICD11: 6A20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 404.5 Topological Polar Surface Area 6.5
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
941361
PubChem SID
7979238 ; 9208288 ; 10525243 ; 14879384 ; 26751607 ; 26751608 ; 44891609 ; 46507129 ; 47216516 ; 47216517 ; 47439976 ; 47515052 ; 47515053 ; 47515054 ; 47515055 ; 47588728 ; 47588729 ; 47736197 ; 48184716 ; 49698432 ; 50011452 ; 50104264 ; 50104265 ; 56365814 ; 57408889 ; 80028030 ; 81093273 ; 85787717 ; 85788409 ; 85788604 ; 90341204 ; 92308837 ; 92309757 ; 92711460 ; 96024666 ; 99300671 ; 99302189 ; 103050123 ; 103096316 ; 103153578 ; 103199419 ; 103928970 ; 104179181 ; 110096637 ; 117509719 ; 124526360 ; 124749784 ; 124883264 ; 124883265 ; 124883266
ChEBI ID
CHEBI:92209
CAS Number
52468-60-7
TTD Drug ID
D05CEU
Formula
C26H26F2N2
Canonical SMILES
C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
InChI
1S/C26H26F2N2/c27-24-12-8-22(9-13-24)26(23-10-14-25(28)15-11-23)30-19-17-29(18-20-30)16-4-7-21-5-2-1-3-6-21/h1-15,26H,16-20H2/b7-4+
InChIKey
SMANXXCATUTDDT-QPJJXVBHSA-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
1-[Bis(4-fluorophenyl)methyl]piperazine DM005746
152932
Oxidation - N-desalkylation 1 [3]
Flunarizine M2 DM006676
6438877
Oxidation - Hydroxylation 1 [3]
Flunarizine M3 DM006677
9582
Oxidation - N-desalkylation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013905 Flunarizine Flunarizine M1 Oxidation - N-desalkylation CYP2C9 ... [3]
MR013906 Flunarizine Flunarizine M2 Oxidation - Hydroxylation CYP2D6 [3]
MR013907 Flunarizine Flunarizine M3 Oxidation - N-desalkylation CYP2C9 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
References
1 ClinicalTrials.gov (NCT00740259) Efficacy and Tolerability of Flunarizine for the Treatment of Schizophrenia: Comparison With Haloperidol.
2 Oxidative metabolism of flunarizine and cinnarizine by microsomes from B-lymphoblastoid cell lines expressing human cytochrome P450 enzymes. Biol Pharm Bull. 1996 Nov;19(11):1511-4.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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