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

General Information of Drug (ID: DR5222)
Drug Name
Cyclizine
Synonyms
Ciclizina; Cyclizinum; Emoquil; Marezine; Nautazine; Valoid; Wellcome; Cyclizine chloride; Cyclizine hydrochloride; Marezine hydrochloride; BW 47-83; Ciclizina [INN-Spanish]; Cyclizine (INN); Cyclizinum [INN-Latin]; Emoquil (TN); Marezine (TN); Marzine (TN); Ne-devomit; Neo-devomit; Reis-fit; Valoid (TN); Wellcome preparation 47-83; Wellcome prepn 47-83; Cyclizine [INN:BAN:DCF]; Wellcome prepn. 47-83; N-Benzhydryl-N'-methylpiperazine; N-Methyl-N'-benzhydrylpiperazine; N-Methyl-N'-benzyhydrylpiperazine; (+-)-1-diphenylmethyl-4-methylpiperazine; (-)-1-Diphenylmethyl-4-methylpiperazine; (N-Benzhydryl)(N'-methyl)diethylenediamine; 1-(Diphenylmethyl)-4-methylpiperazine; 1-Benzhydryl-4-methylpiperazin; 1-Benzhydryl-4-methylpiperazine; 1-Diphenylmethyl-4-methylpiperazine
Indication Nausea [ICD11: MD90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 266.4 Topological Polar Surface Area 6.5
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6726
ChEBI ID
CHEBI:3994
CAS Number
82-92-8
TTD Drug ID
D08HRJ
Formula
C18H22N2
Canonical SMILES
CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3
InChIKey
UVKZSORBKUEBAZ-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
Cinnarizine metabolite M1 DM003163
70048
Oxidation - N-Desmethylation 1 [3]
Monohydroxycyclizine DM018548 N. A. Oxidation - Heteroocyclic Hydroxylation 1 [3]
Monohydroxycyclizine DM018548 N. A. Oxidation - Aromatic Hydroxylation 1 [3]
Hydroxynorcyclizine DM018547 N. A. Oxidation - Heterocyclic Ring Hydroxylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010627 Cyclizine Norcyclizine Oxidation - N-Desmethylation Unclear [3]
MR010629 Cyclizine Monohydroxycyclizine Oxidation - Aromatic Hydroxylation Unclear [3]
MR010628 Norcyclizine Hydroxynorcyclizine Oxidation - Heterocyclic Ring Hydroxylation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Homo sapiens
UDB10_HUMAN
2.4.1.17
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7151).
2 N-glucuronidation catalyzed by UGT1A4 and UGT2B10 in human liver microsomes: Assay optimization and substrate identification
3 Biotransformation of cyclizine in greyhounds. 1: Identification and analysis of cyclizine and some basic metabolites in canine urine by gas chromatography-mass spectrometry

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