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

General Information of Drug (ID: DR0329)
Drug Name
Cinnarizine
Synonyms
Cinarizina; Cinarizina [INN-Spanish]; Cinarizine; Cinazyn; Cinnageron; Cinnarizine [USAN:INN:BAN:JAN]; Cinnarizinum; Cinnarizinum [INN-Latin]; Aplactan; Dimitron; Dimitronal; Folcodal; Glanil; Labyrin; Lazeta; Marisan; Midronal; Mitronal; R 1575; Stugeron; Stutgeron; Stutgin; Toliman; cinnarizine; 1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine; 1-Benzhydryl-4-cinnamylpiperazin; 1-Cinnamyl-4-(diphenylmethyl)piperazine; 298-57-7; 516 MD; Piperazine, 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)-; R 516; Sepan; UNII-3DI2E1X18L
Indication Haemorrhagic stroke [ICD11: 8B20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 368.5 Topological Polar Surface Area 6.5
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
1547484
PubChem SID
145189 ; 597357 ; 855570 ; 7848358 ; 7978948 ; 8652487 ; 10321216 ; 10517604 ; 10852043 ; 14803894 ; 17404877 ; 24278320 ; 32247729 ; 47216936 ; 47440424 ; 47515486 ; 47810927 ; 47810928 ; 48110619 ; 48415781 ; 49698416 ; 50012381 ; 50103929 ; 50103930 ; 50103931 ; 50140413 ; 53777420 ; 56422441 ; 56464175 ; 57288760 ; 57409047 ; 81093277 ; 85148348 ; 85173395 ; 85209898 ; 85231348 ; 85788038 ; 89099692 ; 89850280 ; 90340734 ; 92125122 ; 92303637 ; 103224720 ; 103913696 ; 103928925 ; 106681504 ; 110522301 ; 117706973 ; 121361114 ; 121362793
ChEBI ID
ChEBI:31403
CAS Number
298-57-7
TTD Drug ID
D0Q3YO
Formula
C26H28N2
Canonical SMILES
C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
InChI
1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+
InChIKey
DERZBLKQOCDDDZ-JLHYYAGUSA-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-Cinnamylpiperazine DM003167
86803
Oxidation - N-dealkylation; hydrolysis 1 [5]
Cinnamaldehyde DM003166
637511
Oxidation - N-dealkylation 1 [5]
Cinnarizine metabolite M1 DM003163
70048
Unclear 1 [2]
Cinnarizine metabolite M2 DM003164 N. A. Oxidation - Hydrolyzationn 1 [2]
Cinnarizine metabolite M4 DM003165 N. A. Oxidation - Hydrolyzationn 1 [2]
Benzhydrol DM003162
7037
Unclear 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013303 Cinnarizine Cinnarizine metabolite M1 Unclear CYP2C9 ... [2]
MR013304 Cinnarizine Cinnarizine metabolite M2 Oxidation - Hydrolyzationn CYP2D6 [2]
MR013305 Cinnarizine Cinnarizine metabolite M4 Oxidation - Hydrolyzationn CYP2B6 [2]
MR013306 Cinnarizine Cinnamaldehyde Oxidation - N-dealkylation CYP2C9 ... [5]
MR013307 Cinnarizine 1-Cinnamylpiperazine Oxidation - N-dealkylation; hydrolysis CYP2C9 ... [5]
MR013302 Benzophenone Benzhydrol Unclear Unclear [6]
⏷ Show the Full List of 6 MR(s)
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
[3]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_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
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
⏷ Show the Full List of 7  DME(s)
References
1 The effect of cinnarizine and cocculus indicus on simulator sickness. Physiol Behav. 2007 May 16;91(1):180-90.
2 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.
3 Insights into the substrate specificity, inhibitors, regulation, and polymorphisms and the clinical impact of human cytochrome P450 1A2. AAPS J. 2009 Sep;11(3):481-94.
4 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
5 DrugBank : Cinnarizine
6 Oxidative metabolism of cinnarizine in rat liver microsomes

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